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Journal articles on the topic 'Macrocyclic synthesis'

Author: Grafiati

Published: 4 June 2021

Last updated: 2 February 2022

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1

Singh, Kartikey, and Rama Pati Tripathi. "An Overview on Glyco-Macrocycles: Potential New Lead and their Future in Medicinal Chemistry." Current Medicinal Chemistry 27, no. 20 (June 7, 2020): 3386–410. http://dx.doi.org/10.2174/0929867326666190227232721.

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Macrocycles cover a small segment of molecules with a vast range of biological activity in the chemotherapeutic world. Primarily, the natural sources derived from macrocyclic drug candidates with a wide range of biological activities are known. Further evolutions of the medicinal chemistry towards macrocycle-based chemotherapeutics involve the functionalization of the natural product by hemisynthesis. More recently, macrocycles based on carbohydrates have evolved a considerable interest among the medicinal chemists worldwide. Carbohydrates provide an ideal scaffold to generate chiral macrocycles with well-defined pharmacophores in a decorated fashion to achieve the desired biological activity. We have given an overview on carbohydrate-derived macrocycle involving their synthesis in drug design and discovery and potential role in medicinal chemistry.

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2

Kandemir, Hakan, Ibrahim F. Sengul, Naresh Kumar, and David StC Black. "Synthesis of Imine and Amine-Linked Macrocycles Containing Tris-Indoles." Australian Journal of Chemistry 70, no. 11 (2017): 1196. http://dx.doi.org/10.1071/ch17264.

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The synthesis of 21-membered imine- and amine-linked tris-indole macrocycles starting from 7-nitroethylindoles is described. The 7-nitroethylindoles are converted to 2,2′-diindolylmethanes and the nitro groups reduced to amino. The resulting diamines undergo reactions with indole-2,7-dicarbaldehydes to form the macrocyclic imines, which can subsequently be reduced to the macrocyclic amines.

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3

Merner, Bradley, Nirmal Mitra, and Caroline Merryman. "Highly Strained para-Phenylene-Bridged Macrocycles from Unstrained 1,4-Diketo Macrocycles." Synlett 28, no. 17 (August 22, 2017): 2205–11. http://dx.doi.org/10.1055/s-0036-1589081.

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The conversion of macrocyclic 1,4-diketones to highly strained para-phenylene rings has recently been reported by our laboratory. This synthetic strategy represents a non-cross-coupling-based approach to arene-bridged macrocycles, and an alternative to palladium- and nickel-mediated processes. In this Synpacts article we discuss the development of endgame aromatization protocols for the synthesis of increasingly strained arene systems, as well as potential advantages of the macrocyclic 1,4-diketone approach to selectively functionalized benzenoid macrocycles for future complexity building reactions.1 Introduction2 A Non-Cross-Coupling-Based Approach to Arene-Bridged Macro cycles3 Macrocyclic 1,4-Diketones: Streamlined Synthesis and Size-Dependent Diastereoselective Grignard Reactions4 Dehydrative Aromatization Reactions: A Powerful Tool for Synthesizing Highly Strained para-Phenylene Units5 Conclusion

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4

Lodeiro, Carlos, Rufina Bastida, Emilia Bértolo, and Adolfo Rodríguez. "A new family of NxOy pyridine-containing macrocycles: Synthesis and characterization of their Y(III), Ln(III), Zn(II), and Cd(II) coordination compounds." Canadian Journal of Chemistry 82, no. 3 (March 1, 2004): 437–47. http://dx.doi.org/10.1139/v03-214.

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Reaction between 2,6-bis(2-formylphenoxymethyl)pyridine and N,N-bis(3-aminopropyl)methylamine or tris(2-aminoethyl)amine has been used as the starting point for the synthesis of seven oxa-aza macrocyclic ligands, five of them never reported previously. They all feature different pendant arms, which provide a wide range of coordination possibilities. The Schiff base macrocycles L1 and L4 and their reduced ligands L2 and L5 are derived from 2,6-bis(2-formylphenoxymethyl)pyridine and tris(2-aminoethyl)amine or N,N-bis(3-aminopropyl)methylamine, respectively. The reaction of L1 with salicylaldehyde forms L3, which features an imine bond in the pendant arm. The ligand L5 has been the precursor for the pendant-armed L6 and L7, by alkylation of the free NH groups with methyl-imidazole or methyl-indole. By a template or a nontemplate approach, we have synthesized different mono- and dinuclear complexes with Y(III), Ln(III), Zn(II), and Cd(II) cations. Both the free macrocyclic ligands and their corresponding metal complexes have been characterized by microanalysis, IR, UVvis, 1H and 13C NMR spectroscopy, FAB mass spectrometry, MS electrospray, and conductivity measurements.Key words: Schiff-base macrocycle, template synthesis, macrocyclic ligand complexes, lanthanide(III) complexes.

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5

Batiste, Suzanne M., and Jeffrey N. Johnston. "Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control." Proceedings of the National Academy of Sciences 113, no. 52 (December 14, 2016): 14893–97. http://dx.doi.org/10.1073/pnas.1616462114.

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Macrocyclic small molecules are attractive tools in the development of sensors, new materials, and therapeutics. Within early-stage drug discovery, they are increasingly sought for their potential to interact with broad surfaces of peptidic receptors rather than within their narrow folds and pockets. Cyclization of linear small molecule precursors is a straightforward strategy to constrain conformationally mobile motifs, but forging a macrocycle bond typically becomes more difficult at larger ring sizes. We report the development of a general approach to discrete collections of oligomeric macrocyclic depsipeptides using an oligomerization/macrocyclization process governed by a series of Mitsunobu reactions of hydroxy acid monomers. Ring sizes of 18, 24, 30, and 36 are formed in a single reaction from a didepsipeptide, whereas sizes of 24, 36, and 60 result from a tetradepsipeptide. The ring-size selectivity inherent to the approach can be modulated by salt additives that enhance the formation of specific ring sizes. Use of chemical synthesis to prepare the monomers suggests broad access to functionally and stereochemically diverse collections of natural product-like oligodepsipeptide macrocycles. Two cyclodepsipeptide natural products were prepared along with numerous unnatural oligomeric congeners to provide rapid access to discrete collections of complex macrocyclic small molecules from medium (18) to large (60) ring sizes.

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6

Moon, Dohyun, Yong Pyo Hong, and Jong-Ha Choi. "Spectroscopic characterization and molecular structure of 3,14-dimethyl-2,6,13,17-tetraazapentacyclo[16.4.0.12,17.16,13.07,12]tetracosane." Acta Crystallographica Section C Structural Chemistry 72, no. 9 (August 25, 2016): 701–4. http://dx.doi.org/10.1107/s2053229616013280.

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Constrained cyclam derivatives have been found to exhibit anti-HIV effects. The strength of binding to the CXCR4 receptor correlates with anti-HIV activity. The conformation of the macrocyclic compound is very important for co-receptor recognition. Therefore, knowledge of the conformation and crystal packing of macrocycles has become important in developing new highly effective anti-HIV drugs. Structural modifications of N-functionalized polyaza macrocyclic compounds have been achieved using various methods. A new synthesis affording single crystals of the title tetraazapentacyclo[16.4.0.12,17.16,13.07,12]tetracosane macrocycle, C22H40N4, is reported. Formaldehyde reacts readily at room temperature with the tetraazatricyclo[16.4.0.02,17]docosane precursor to yield a macropolycycle containing two five-membered rings. Characterization by elemental, spectroscopic and single-crystal X-ray diffraction analyses shows that the asymmetric unit contains half of a centrosymmetric molecule. The molecular structure shows atransconformation for the two methylene bridges owing to molecular symmetry. The crystal structure is stabilized by intramolecular C—H...N hydrogen bonds. NMR and IR spectroscopic properties support the methylene-bridged macrocyclic structure.

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7

Liu, Na, Xing Wang, Hui Cao, Chun Hai Chen, and Wan Jin Zhang. "Synthesis of a Novel Hollow Sphere Having Rigid Binaphthyl Macrocycle as Shell." Solid State Phenomena 121-123 (March 2007): 219–22. http://dx.doi.org/10.4028/www.scientific.net/ssp.121-123.219.

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A novel hollow sphere having rigid binaphthyl macrocycle as shell was prepared by means of sacrifice the silica core. The synthesis of hollow sphere from rigid colloidal silica particles occurs in three steps: a) modification of silica particles with vinyltriethoxysilane as coupling agent, b) immersion in the solution of monomer having rigid binaphthyl macrocycle and polymerization, and c) removal of silica particles. These macrocycles contained in the shell of hollow spheres belong to an important class of host-guest macrocyclic material in which the rigid backbone and C2 symmetry of the binaphthyl unit play an important role in complexing guest molecules. This will endow hollow sphere with new opportunities in molecular recognition and separation.The morphology of colloidal silica particles and hollow spheres was characterized by SEM and TEM.

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8

Pomarico, Giuseppe, Manuela Stefanelli, Sara Nardis, Sara Lentini, Daniel O. Cicero, Gregory T. McCandless, Kevin M. Smith, and Roberto Paolesse. "Synthesis and functionalization of β-alkyl-meso-triarylcorroles." Journal of Porphyrins and Phthalocyanines 19, no. 07 (July 2015): 865–73. http://dx.doi.org/10.1142/s1088424615500613.

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After the definition of efficient synthetic routes for the preparation of triarylcorroles, the functionalization of these macrocycles is becoming a necessary and challenging field of research. One important synthetic step is the introduction of substituents able to influence the electronic distribution in the macrocyclic ring. A valuable target would be a corrole macrocycle with some β-pyrrole positions occupied by methyl groups, while exploiting other positions to introduce electron-withdrawing substituents. To explore the scope of this approach, we investigated the bromination and the nitration of the corrole ring and the desired products have been obtained in moderate to good yield. The successful preparation of selectively halogenated corroles is particularly interesting since they are suitable substrates for the preparation of more complex partially alkylated structures using modern cross coupling methodologies.

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9

Chmielewski, Michał J., Tomasz Zieliński, and Janusz Jurczak. "Synthesis, structure, and complexing properties of macrocyclic receptors for anions." Pure and Applied Chemistry 79, no. 6 (January 1, 2007): 1087–96. http://dx.doi.org/10.1351/pac200779061087.

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Understanding of structure-affinity relationships is crucial for rational receptor design, however, such studies for anion receptors are still limited. Therefore, we investigated this issue in the case of amide-based macrocyclic receptors derived from aromatic diacids (i.e., isophthalic and dipicolinic). Using these model compounds, we examined the macrocyclic effect, the influence of intramolecular hydrogen bonds, and the correlation between the ring size and anion affinity. We found that in contrast to what was known for acyclic diamides, macrocyclic isophthalamide receptors bind anions more weakly than their dipicolinic analogs. Comprehensive structural studies revealed that such behavior is due to intramolecular hydrogen bonds present in isophthalamide receptors. Furthermore, we demonstrated how this obstacle can be overcome by the preparation of a hybrid macrocycle based on both building blocks.

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10

Srinivas, Avula, and Enugala Kalyan Rao. "Synthesis and Anticancer Activity of Triazole Linked Macrocycles and Heterocycles." Acta Chimica Slovenica 68, no. 2 (June 15, 2021): 404–13. http://dx.doi.org/10.17344/acsi.2020.6466.

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Synthesis of macrocylic enones starting from alkyl ether and triazole as a linker was achieved using click reaction and intramolecular aldol condensation. The newly synthesized macrocyclic enone was successfully utilized as a dipolarophile in 1,3-dipolar cycloaddition. The dipoles generated from hydrazine hydrochloride, hydroxylamine and guanidine hydrochloride were reacted with macrocyclic enone to give a new class of spiro aminopyrimidines, phenyl pyrazoles and isoxazoles grafted macrocycles in good yield. The structures of newly synthesized compounds were confirmed with IR, NMR and mass spectroscopy and evaluated for their anti cancer activity.

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11

Shurpik, Dmitriy N., Alan A. Akhmedov, Peter J. Cragg, Vitaliy V. Plemenkov, and Ivan I. Stoikov. "Progress in the Chemistry of Macrocyclic Meroterpenoids." Plants 9, no. 11 (November 15, 2020): 1582. http://dx.doi.org/10.3390/plants9111582.

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In the last decade, the chemistry of meroterpenoids—conjugated molecules formed from isoprenyl fragments through biosynthetic pathways—has developed rapidly. The class includes some natural metabolites and fully synthetic fragments formed through nonbiological synthesis. In the field of synthetic receptors, a range of structures can be achieved by combining fragments of different classes of organic compounds into one hybrid macrocyclic platform which retains the properties of these fragments. This review discusses the successes in the synthesis and practical application of both natural and synthetic macrocycles. Among the natural macrocyclic meroterpenoids, special attention is paid to isoprenylated flavonoids and phenols, isoprenoid lipids, prenylated amino acids and alkaloids, and isoprenylpolyketides. Among the synthetic macrocyclic meroterpenoids obtained by combining the “classical” macrocyclic platforms, those based on cyclodextrins, together with meta- and paracyclophanes incorporating terpenoid fragments, and meroterpenoids obtained by macrocyclization of several terpene derivatives are considered. In addition, issues related to biomedical activity, processes of self-association and aggregation, and the formation of host–guest complexes of various classes of macrocyclic merotenoids are discussed in detail.

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12

Thirunarayanan, Ayyavu, Sivasamy Selvarani, Gracia Francisco, and Perumal Rajakumar. "Efficient Straightforward Synthesis of Amidopiperazinophanes as Versatile Novel Supramolecular Scaffolds." SynOpen 03, no. 04 (October 2019): 157–63. http://dx.doi.org/10.1055/s-0039-1690333.

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A simple one-pot synthesis of amidopiperazinophanes with a combination of electron-deficient amide groups and electron-rich alkyne and piperazine functionalities has been achieved by using multicomponent reaction (MCR) methodology with the Mannich reaction. Herein, we demonstrate the synthesis of macrocyclic amide structures in good yields. These macrocycles, with electron donor/acceptor sites, are versatile molecules for host–guest and binding.

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13

Atkinson, Ian M., Davar M. Boghai, Leonard F. Lindoy, Bahram Ghanbari, George V. Meehan, and Vinod Saini. "New Macrocyclic Ligands. VIII Di- and Tri-linked Macrocyclic Systems Incorporating N2O2-Donor Atoms." Australian Journal of Chemistry 52, no. 5 (1999): 351. http://dx.doi.org/10.1071/ch99054.

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The synthesis and characterization of new lipophilic di- and tri-linked O2N2-donor macrocycles is reported. The synthesis of the dilinked species involved the initial alkylation of one secondary nitrogen of the parent 15-membered, O2N2-donor macrocycle (1) with 2-bromoethanol or with ethylene oxide to yield (2), followed by protection of the appended alcohol group by reaction with t-butyldiphenylsilyl chloride to give (3). Two such moieties were then bridged via a diacylation reaction with ClCO(CH2)8COCl to yield the corresponding diamide product (4). Deprotection of the alcohol functions followed by reduction of the both amide linkages resulted in formation of theN,N′-alkyl-linked species (5) incorporating two pendant hydroxyethyl groups. This product was then converted [via the corresponding dichloro derivative (6)] into the diether (7) by condensation with 4-t-butylphenol. By use of analogous chemistry, the trilinked trismacrocycle species (12), based on a phloroglucinol core, has also been synthesized. An aim of the present study was thus the preparation of new ‘linked’ macrocyclic systems that might be expected to show higher lipophilicity than their corresponding single-ring systems. These were designed for future use as ionophores in metal ion membrane transport (and solvent extraction) experiments.

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14

Mpassi, Michel, Gérald Guillaumet, Gérard Coudert, Madeleine Tissier, and Jean Juillard. "Macrocycles polyoxygénés à structure benzodioxinique. Synthèse et étude de la complexation du sodium et du potassium dans le methanol." Canadian Journal of Chemistry 67, no. 7 (July 1, 1989): 1132–38. http://dx.doi.org/10.1139/v89-170.

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The synthesis of two new series of polyoxygenated macrocyclic derivatives, 1 and 2, was realised. All these compounds have a 1,4-benzodioxinic moiety and are related to crown ethers, benzocrown ethers, and lariat ethers. The complexing properties of sodium and potassium ions were studied using potentiometry in methanol; results thus obtained are compared to data, previously reported in the literature, for classical polyoxygenated macrocyclic compounds. Keywords: polyoxygenated macrocycles, 1,4-benzodioxin, lariat ethers, sodium and potassium complexes, solvent methanol.

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15

Maurya, Sushil K., and Rohit Rana. "An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks." Beilstein Journal of Organic Chemistry 13 (June 9, 2017): 1106–18. http://dx.doi.org/10.3762/bjoc.13.110.

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An efficient, eco-compatible diversity-oriented synthesis (DOS) approach for the generation of library of sugar embedded macrocyclic compounds with various ring size containing 1,2,3-triazole has been developed. This concise strategy involves the iterative use of readily available sugar-derived alkyne/azide–alkene building blocks coupled through copper catalyzed azide–alkyne cycloaddition (CuAAC) reaction followed by pairing of the linear cyclo-adduct using greener reaction conditions. The eco-compatibility, mild reaction conditions, greener solvents, easy purification and avoidance of hazards and toxic solvents are advantages of this protocol to access this important structural class. The diversity of the macrocycles synthesized (in total we have synthesized 13 macrocycles) using a set of standard reaction protocols demonstrate the potential of the new eco-compatible approach for the macrocyclic library generation.

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16

Ndibwami, Alexis, Serge Lamothe, Daniel Guay, Raymond Plante, Pierre Soucy, Solo Goldstein, and Pierre Deslongchamps. "Transannular Diels–Alder reactions on 14-membered macrocyclic trienes. Part I: stereoselective syntheses of the macrocyclic trienes precursors." Canadian Journal of Chemistry 71, no. 5 (May 1, 1993): 695–713. http://dx.doi.org/10.1139/v93-094.

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Transannular Diels–Alder reactions on 14-membered macrocycles containing properly located diene and methyl-substituted dienophile units lead to A.B.C.[6.6.6] tricycles related to steroids. To study the influence of the olefin and diene geometry on the stereochemical outcome of the Diels–Alder reaction it was necessary to prepare macrocyclic trienes of well-defined stereochemistry. Eight different types of macrocyclic trienes might be obtained by the coupling of appropriate dienophiles and dienes, namely, TTC, TTT, TCC, TCT, CTC, CTT, CCC, and CCT. In this paper (first in a series of two), the synthesis of appropriately functionalized dienophile and diene synthons, as well as their coupling reaction affording macrocyclic triene precursors, is described.

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17

Gu, Meng-Di, Yao Lu, and Mei-Xiang Wang. "Synthesis and anion binding properties of phthalimide-containing corona[6]arenes." Beilstein Journal of Organic Chemistry 15 (August 21, 2019): 1976–83. http://dx.doi.org/10.3762/bjoc.15.193.

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Functionalized O6-corona[3]arene[3]tetrazines were synthesized efficiently and conveniently by means of a macrocyclic condensation reaction between N-functionalized 3,6-dihydroxyphthalimides and 3,6-dichlorotetrazine under mild conditions in a one-pot reaction manner. The novel macrocycles exist as a mixture of rapidly interconvertible conformers in solution while in the solid state they adopt the conformation in which three phthalimide units are cis,trans-orientated. Acting as electron-deficient macrocyclic hosts, the synthesized O6-corona[3]arene[3]tetrazines self-regulated conformational structures to complex anions in the gas phase and in the solid state owing to the anion–π noncovalent interactions between anions and the tetrazine rings.

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18

He, Zhenfeng, Yufeng Huo, Chao Wang, Duo Pan, Binbin Dong, Mingli Wang, Li Guo, Zhuolin Hu, and Zhanhu Guo. "Synthesis of dynamic imine macrocyclic supramolecular polymers via synchronized self-assembly based on dynamic covalent bonds and noncovalent interactions." Chemical Communications 56, no. 65 (2020): 9288–91. http://dx.doi.org/10.1039/d0cc02991b.

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19

Fenton, Ronald R., Leonard F. Lindoy, Jason R. Price, Brian W. Skelton, and Allan H. White. "New Macrocyclic Ligands. XVI. Synthesis of a Series of N-Benzylated Macrocycles Incorporating N4O2-Donor Set." Australian Journal of Chemistry 56, no. 11 (2003): 1141. http://dx.doi.org/10.1071/ch03079.

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The synthesis of five 20-membered, N-benzylated macrocyclic ligands incorporating N4O2-donor sets and from one to three benzyl substituents for use in metal-ion recognition studies is described. The new derivatives were obtained by both benzylation of the pre-formed parent macrocycle using benzyl chloride in acetonitrile in the presence of base or, in one case, by performing macrocyclic ring closure using the appropriate N-benzylated triamine precursor by means of a bis-Schiff base condensation with the corresponding dialdehyde, followed by in situ reduction of the diamine linkages so formed. The single crystal X-ray structure of the symmetrically substituted, di-N-benzylated derivative is reported.

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20

Hilvano, Edward Gabrielle V., Guang Yang, Inno A. Emnacen, Elena V. Rybak-Akimova, Junie B. Billones, Maria Constancia O. Carrillo, Bruce C. Noll, and Voltaire G. Organo. "Synthesis and crystal structure of [2,7,12-trimethyl-3,7,11,17-tetraazabicyclo[11.3.1]heptadeca-1(17),13,15-triene-κ4N]copper(II) bis(perchlorate)." Acta Crystallographica Section E Crystallographic Communications 72, no. 7 (June 21, 2016): 1009–12. http://dx.doi.org/10.1107/s2056989016009701.

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The title copper(II) complex of a pyridine-containing macrocycle (PyMAC), [Cu(C16H28N4)](ClO4)2, has been prepared. The crystal structure reveals the CuIIatom to be octahedrally coordinated by a tetradentate aminopyridine macrocyclic ligand surrounding the metal cation in a square-planar geometry. Two weakly bound perchlorate counter-ions occupy the axial sites above and below the macrocyclic plane. The crystal studied was refined as a two-component pseudo-merohedral twin; the refined fractional contribution of the minor component is 38.77 (8)%

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21

Yampolska, H., S. Kharchenko, A. Kozytskyi, A. Kyrylchuk, Z. Voitenko, and O. Grygorenko. "SYNTHESIS OF A 1,2,3-TRIAZOLE-CONTAINING MACROCYCLE BASED ON THE "CLICK CHEMISTRY" REACTION AND ANALYSIS OF ITS PLANAR CHIRALITY USING NMR AND DFT CALCULATIONS." Bulletin of Taras Shevchenko National University of Kyiv. Chemistry, no. 1 (57) (2020): 55–61. http://dx.doi.org/10.17721/1728-2209.2020.1(57).14.

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Macrocycles represent previously unexplored promising drug candidates, that can be useful for treating protein-protein interactions. Atropoisomerism is an inherent feature of the natural macrocyclic peptides that is significant for their activity and selectivity, and, therefore, should be introduced into newly synthesized macrocycles. Synthesis of the libraries of artificial macrocycles faces many challenges due to their structure and size. Herein we report on the preparation of a 16-membered macrocycle containing 1,2,3-triazole ring, spiro-piperidine, and phenyl moieties, as well as a chiral carbon atom. Our approach to the macrocycle was inspired by the "build/couple/pair" (B/C/P) strategy, a part of diversity-oriented synthesis methodology. We have employed readily accessible starting materials and robust synthetic procedures which allowed us to obtain the target macrocycle in a high yield. Standard methods of amide bond formation were used for the coupling of macrocycle building blocks. Click chemistry azide-alkyne cycloaddition was exploited at the final ring closure step. The assignment of signals in 1H and 13C NMR spectra of the macrocycle was performed using a series of 2D NMR techniques. The macrocycle displayed planar chirality, which, in a combination with a stereocenter with the known configuration, was sufficient to propose possible structures of diastereomers. The diastereomers could differ by the relative position of triazole ring. Their racemization could occur through a "rope skipping" motion involving the cyclic chain crossing the plane of 1,2,3-triazole ring. The supposed structures of diastereomers were corroborated by means of a various NMR spectroscopy techniques and DFT calculations. Analysis of the amide NH chemical shift temperature coefficients coupled with the data on optimized geometries obtained by DFT convincingly demonstrated that the intramolecular hydrogen bonds play a major role in stabilization of the diastereomer structures. According to the variable temperature NMR experiment, the interconversion of two diastereomers did not occur even at heating up to 70 °C.

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22

Lízal, Tomáš, and Vladimír Šindelář. "Bambusuril analogs based on alternating glycoluril and xylylene units." Beilstein Journal of Organic Chemistry 15 (June 11, 2019): 1268–74. http://dx.doi.org/10.3762/bjoc.15.124.

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The glycoluril monomer is a popular building block in supramolecular chemistry as it is used for the synthesis of versatile host molecules which can interact with cationic, anionic or neutral guest molecules. Here we present the design and synthesis of a new hybrid macrocycle containing glycoluril and aromatic units. The reaction afforded a mixture of macrocyclic homologues from which a two-membered macrocycle was isolated as the main product. Two disastereomers of the macrocycle were separated and characterized by means of NMR spectroscopy and X-ray crystallography. Conformational changes of these diastereomers were investigated using DFT models and variable-temperature NMR.

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23

Kumar, Anuj, and Vinod Kumar Vashistha. "Design and synthesis of CoIIHMTAA-14/16 macrocycles and their nano-composites for oxygen reduction electrocatalysis." RSC Advances 9, no. 23 (2019): 13243–48. http://dx.doi.org/10.1039/c9ra02169h.

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The major concerns in the design of macrocycle based-ORR catalysts are understanding the macrocyclic, π-conjugation, central metal and substituent effects on electrocatalysis; and their use on the electrode surface for the retention of activity due to poor stability.

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24

Lapenta, Rosita, Nicola Alessandro De Simone, Antonio Buonerba, Carmen Talotta, Carmine Gaeta, Placido Neri, Alfonso Grassi, and Stefano Milione. "Dinuclear zirconium complex bearing a 1,5-bridged-calix[8]arene ligand as an effective catalyst for the synthesis of macrolactones." Catalysis Science & Technology 8, no. 10 (2018): 2716–27. http://dx.doi.org/10.1039/c7cy02537h.

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“Macrocyclization of Cycles with a Macrocycle.” The intramolecular cooperation of metal centres in a novel dinuclear complex has been postulated as responsible for the observed high rate of formation of macrocyclic polyesters.

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25

Thapa, Rajesh, and Stefan M. Kilyanek. "Synthesis and structural characterization of iridium(I) complexes of 20-membered macrocyclic rings bearing chelating bis(N-heterocyclic carbene) ligands." Acta Crystallographica Section C Structural Chemistry 75, no. 12 (November 25, 2019): 1652–57. http://dx.doi.org/10.1107/s2053229619015006.

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The reactivities of two 20-membered macrocyclic ligands, each containing two N-heterocyclic carbene (NHC) and two amine groups, towards [IrCl(COD)]2 (COD is cycloocta-1,5-diene) were investigated. Macrocycles containing imidazolin-2-ylidene groups formed the monometallic complex [(1,2,5,6-η)-cycloocta-1,5-diene](5,16-dibenzyl-1,5,9,12,16,20-hexaazatricyclo[18.2.1.19,12]tetracosa-10,21-dien-21,22-diylidene)iridium(I) bromide dichloromethane monosolvate, [Ir(C8H12)(C32H42N6)]Br·CH2Cl2, 2a. The structure of iridium complex 2a at 100 K has triclinic P\overline{1} symmetry. The ligand in 2a coordinates to the Ir center through the NHC moieties in a cis fashion. Additionally, the ligand adopts an umbrella-like structure that appears to envelope the Ir center. The structure displays C—H...Br interactions. Macrocycles containing benzimidazolin-2-ylidene groups formed the bimetallic complex [μ-5,20-dibenzyl-1,5,9,16,20,24-hexaazapentacyclo[22.6.1.19,16.010,15.025,30]dotriaconta-10(15),11,13,25(30),26,28-hexaene-31,32-diylidene]bis{bromido[(1,2,5,6-η)-cycloocta-1,5-diene]iridium(I)}, [Ir2Br2(C8H12)2(C40H46N6)], 2b. The structure of complex 2b at 100 K has orthorhombic Pbca symmetry. Each NHC moiety in 2b coordinates in a monodentate fashion to an Ir(COD) fragment. The structure exhibits disorder of the main molecule. This disorder is found in the portion of the macrocycle containing an amine group. This structure also displays C—H...Br interactions. Finally, the structure of the hexafluorophosphate salt of the imidazolin-2-ylidene-containing macrocycle, namely 5,16-dibenzyl-1λ5,5,9,12λ5,16,20-hexaazatricyclo[18.2.1.19,12]tetracosa-1(23),10,12(24),21-tetraene-1,12-diium bis(hexafluorophosphate), C32H44N6 2+·2PF6 −, 1c, was determined. The structure of macrocycle 1c at 100 K has triclinic P\overline{1} symmetry and was found to contain C—H...F interactions.

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26

Muranaka, Atsuya, Fumiko Kyotani, Xingmei Ouyang, Daisuke Hashizume, and Masanobu Uchiyama. "Synthesis and properties of palladium(II) complexes of aromatic hemiporphyrazines." Journal of Porphyrins and Phthalocyanines 18, no. 10n11 (October 2014): 869–74. http://dx.doi.org/10.1142/s1088424614500667.

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Palladium(II) complexes of aromatic hemiporphyrazines were prepared by the reaction of bis(dibenzylideneacetone)palladium(0) with the corresponding metal-free macrocycles. Single crystal X-ray analysis revealed that a palladium(II) ion was coordinated inside the macrocyclic cavity to form two Pd – C bonds. Electronic properties of the metalloorganic compounds were characterized by NMR, UV-vis-NIR, and magnetic circular dichroism (MCD) spectroscopy.

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27

Yousaf, Muhammad, Ximena Zarate, Eduardo Schott, Alan J. Lough, and Bryan D. Koivisto. "Photophysical behaviour of BODIPY-phenylacetylene macrocyclic dyads for light-harvesting applications." RSC Advances 8, no. 50 (2018): 28533–37. http://dx.doi.org/10.1039/c8ra03384f.

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The synthesis and study of a family of BODIPY-phenylacetylene macrocycles where donor groups have been added to the macrocycle in order to tune the physicochemical properties and absorption profile is reported.

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28

Butler, Eibhlin, Lucia Florentino, Damien Cornut, Gonzalo Gomez-Campillos, Hao Liu, Andrew C. Regan, and Eric J. Thomas. "Synthesis of macrocyclic precursors of the vioprolides." Organic & Biomolecular Chemistry 16, no. 38 (2018): 6935–60. http://dx.doi.org/10.1039/c8ob01756e.

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Convergent syntheses have been developed of macrocycles that may be useful for the synthesis of vioprolide D. Preliminary studies have also been carried out into the introduction of the thiazoline and (E)-dehydrobutyrine components.

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29

Xu, Yao-Chang, Andrew L. Roughton, Pierre Soucy, Solo Goldstein, and Pierre Deslongchamps. "Stereocontrolled construction of 1,7-dimethyl A.B.C.[6.6.6] tricycles. Part II. Transannular Diels–Alder reaction of 14-membered macrocycles containing cis-dienophiles." Canadian Journal of Chemistry 71, no. 8 (August 1, 1993): 1169–83. http://dx.doi.org/10.1139/v93-153.

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The synthesis and transannular Diels–Alder reactions of 14-membered macrocyclic trienes containing a methyl-substituted diene and a methyl-substituted cis-dienophile moiety are described. As a result of the dienophile cis geometry the 1,7-dimethyl A.B.C.[6.6.6] tricycles obtained from the Diels–Alder reaction have a different stereochemistry at the four chiral centers than similar tricycles that were the subject of the preceding paper in this series. Thus trans-syn-cis (TSC) tricycle 30 was the sole product obtained from the trans-cis-cis (TCC) macrocycle 1b. In a similar fashion TCC macrocycle 1d afforded only trans-syn-cis (TSC) tricycle 31. On the contrary, the transannular Diels–Alder reaction in cis-trans-cis (CTC) macrocycle 1a and trans-trans-cis (TTC) macrocycle 1c led to a mixture of the same four tricyclics (30, 32–34) but in different ratio. The above experimental results are rationalized by taking into consideration the interconversion of macrocyclic trienes 1a, 1b, and 1c. Pathways for these interconversions are also proposed.

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30

Lehn, Jean-Marie, and Pierre G. Potvin. "Synthesis of rigid, chiral 1,5-diamino-3-oxapentanes and incorporation into chiral macrocyclic polyether ligands." Canadian Journal of Chemistry 66, no. 1 (January 1, 1988): 195–200. http://dx.doi.org/10.1139/v88-032.

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The syntheses of 2,5-anhydro-1,6-di-C-amino-1,6-dideoxy-3,4-di-O-methyl-D-mannitol 11 and its N,N′-dimethyl analogue 15 are described, as are couplings to bis-tartaro-18-crown-6 1 to give a macrobicyclic cryptand 16, and macrocycles 17 and 18 bearing four lateral groups, which are potential precursors of a cylindrical stacked macrocyclic system such as 6.

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31

Elizbarashvili, Elizbar, Tea Matitaishvili, and Khatuna Topuria. "Synthesis of macrocyclic polyazomethines." Journal of the Brazilian Chemical Society 18, no. 6 (2007): 1254–58. http://dx.doi.org/10.1590/s0103-50532007000600022.

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32

Fuhrmann, G., J. Krömer, and P. Bäurele. "Synthesis of macrocyclic oligothiophenes." Synthetic Metals 119, no. 1-3 (March 2001): 125–26. http://dx.doi.org/10.1016/s0379-6779(00)01173-5.

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33

DanielFigueroa-Villar, José, and Fábio C. Clemente. "Synthesis of Macrocyclic Barbiturates." Synthetic Communications 28, no. 23 (December 1998): 4325–32. http://dx.doi.org/10.1080/00397919808004466.

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34

Chak, B. CM, and A. McAuley. "The synthesis and characterization of the pendant-armed ligand N,N′-bis(2′-pyridylmethyl)-1,7-dithia-4,11-diazacyclotetradecane (L4) and crystal structures of L4 and the copper(II) complex [Cu(L4)](ClO4)2 Crystal structure of the nickel(II) complex of N-(2′-pyridylmethyl)-1,4,7-trithia-11-azacyclotetradecane (L2), [Ni(L2)(CH3CN)](ClO4)2·CH3CN." Canadian Journal of Chemistry 84, no. 2 (February 1, 2006): 187–95. http://dx.doi.org/10.1139/v05-241.

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The synthesis and characterization of the mixed donor ligand N,N′-bis(2′-pyridylmethyl)-1,7-dithia-4,11-diazacyclotetradecane (L4) containing two pendant pyridine arms is described. The macrocycle formation involves reaction of N-tosylbis(2-bromoethyl)amine with N-tosylbis(3-mercaptopropyl)amine at high dilution followed by detosylation at the nitrogen atoms using LiAlH4 in view of the presence of the thioether groups. An X-ray study of the ligand shows the sulphur atoms lie exo to the macrocyclic ring. The nickel(II) and copper(II) complexes of L4 have been characterized and the X-ray structure of the Cu(II) ion exhibits a five-coordinate copper ion despite the presence of six available donor atoms. In the case of ligand N-(2-pyridylmethyl)-1,4,7-trithia-11-azacyclotetradecane (L2), with a single pendant N donor, the Ni(II) complex is distorted octahedral with a molecule of acetonitrile in the sixth site. Details of UVvis, ESR spectra, and electrochemical studies on the complexes are presented.Key words: synthesis, pendant-armed, mixed donor S,N macrocycles, copper, nickel.

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35

Mitchell, Gavin M., Amelia Hesketh, Christie Lombardi, Cally Ho, and Thomas M. Fyles. "A membrane-spanning macrocyclic bolaamphiphile lipid mimic of archaeal lipids." Canadian Journal of Chemistry 95, no. 3 (March 2017): 253–62. http://dx.doi.org/10.1139/cjc-2016-0252.

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The synthesis of a 72-membered macrocyclic tetraester bolaamphiphile is accomplished in six chemical steps from commercially available starting materials using copper-accelerated azide–alkyne coupling to close the macrocycle in high yield. Related diester amphiphiles and an acyclic tetraester bolaamphiphile were also prepared. The set of lipids bearing nitrophenyl phosphate head groups were incorporated into phospholipid vesicles but failed to undergo phosphate hydrolysis in basic conditions, undergoing efficient elimination in competition. The same lipid cores bearing phosphate-linked nitrobenzoxadiazole (NBD) head groups also incorporated into phospholipid vesicles and the NBD fluorescence was quenched with cobalt ions. The proportion of membrane-spanning bolaamphiphiles was determined from the ratio of cobalt quenching in the presence and in the absence of a detergent. The macrocyclic bolaamphiphile is incorporated into phospholipid vesicles such that 48 ± 4% of the NBD head groups are in the outer leaflet, consistent with a membrane-spanning orientation. The acyclic bolaamphiphile is incorporated with 75 ± 3% of the NBD head groups accessible to quencher in the absence of a detergent suggesting U-shaped incorporation in the outer leaflet of the bilayer membrane. In ring size and spanning ability, the macrocyclic bolaamphiphile mimics naturally occurring macrocyclic archaeal lipids.

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36

SHARMAN, W. M., and J. E. VAN LIER. "Use of palladium catalysis in the synthesis of novel porphyrins and phthalocyanines." Journal of Porphyrins and Phthalocyanines 04, no. 05 (August 2000): 441–53. http://dx.doi.org/10.1002/1099-1409(200008)4:5<441::aid-jpp275>3.0.co;2-a.

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Palladium catalysts offer a rich and highly versatile chemistry for the synthesis of novel porphyrins and phthalocyanines. These mild and flexible reactions have been used extensively in the preparation of interesting porphyrins and phthalocyanines, either in the synthesis of substituted precursors or in the modification of pre-existing macrocycles. For these tetrapyrrolic compounds, metal-mediated reactions such as these offer extensive benefits, which have been taken advantage of in order to add novel substituents, synthesize naturally occurring molecules and prepare multi-macrocyclic arrays. This review gives an overview of the use of palladium catalysts in the synthesis of porphyrins and phthalocyanines along with the applications of some of the compounds prepared.

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37

Ebadi, Abdol Ghaffar, and Somayeh Alami. "Synthesis of Nano Machines Based on Catenanes and Rotaxanes." Applied Mechanics and Materials 110-116 (October 2011): 3807–9. http://dx.doi.org/10.4028/www.scientific.net/amm.110-116.3807.

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A nanomachine is an assembly of a discrete number of supramolecular components designed to perform mechanical like movements as a consequence of appropriate external stimuli. In this research work we wish report synthesis of a part of nanomachines are based on interlocked macrocycle named rotaxanes, catenanes, pseudorataxane and knots, that Bis aza thiacrown compound (5) was synthesized by macrocyclic diamide (4) and 2, 6-dicarbonyldicholoride pyridine in dry CH2Cl2 and was refluxed in presence of Et3N in good yield. The structures of these compounds were confirmed by IR, 1H NMR, 13C NMR and elemental analysis.

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38

Tykwinski, Rik R., Mojtaba Gholami, Sara Eisler, Yuming Zhao, Frederic Melin, and Luis Echegoyen. "Expanded radialenes: Modular synthesis and properties of cross-conjugated enyne macrocycles." Pure and Applied Chemistry 80, no. 3 (January 1, 2008): 621–37. http://dx.doi.org/10.1351/pac200880030621.

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During the past two decades, shape-persistent conjugated macrocycles with a broad spectrum of attributes and topologies have been synthesized. This includes macrocycles with remarkable electronic, optical, and supramolecular properties, as well as intriguing frameworks. Expanded radialenes are a class of conjugated shape-persistent macrocycles that arise from the formal insertion of acetylene units into a radialene framework. A related class of macrocycles, the expanded radiaannulenes, contains both endo- and exocyclic vinylene and vinylidene segments, respectively, and accordingly exhibits properties intermediate between radialenes and annulenes. Enyne building blocks have been developed that are suitable for forming a macrocyclic framework through a step-wise sequence of Pd-catalyzed cross-coupling reactions. This "building-block" approach allows us to explore a range of molecular architectures that will ultimately provide for an understanding of π-delocalization in these compounds. The synthesis and structural characterization of the first members of this new class of expanded radialenes and radiaannulenes are described.

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39

Singh, Dharmpal, and Krishan Kumar. "Macrocyclic complexes: Synthesis and characterization." Journal of the Serbian Chemical Society 75, no. 4 (2010): 475–82. http://dx.doi.org/10.2298/jsc091021028s.

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A novel series of complexes of the type [M(C28H24N4)X]X2, where M = Cr(III), Fe(III) or Mn(III), X = Cl?, NO3 ?, CH3COO? and (C28H24N4) corresponds to the tetradentate macrocyclic ligand, were synthesized in methanolic media by the template condensation of 1,8-diaminonaphthalene and 2,3- butanedione (diacetyl) in the presence of trivalent metal salts. The complexes were characterized by elemental analyses, conductance and magnetic measurements, and UV/Vis, NMR and IR spectroscopy. Based on these studies, a five-coordinate square pyramidal geometry for all the prepared complexes is proposed. All the synthesized macrocyclic complexes were tested for their in vitro antifungal activity against some fungal strains viz. Aspergillus niger and A. fumigatus. The results obtained were compared with the standard antifungal drug fluconazole.

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40

Bosseray, Pascal, Gérard Coudert, Gérald Guillaumet, Georges Jeminet, Madeleine Tissier, and Jean Juillard. "Polyether carboxylic acids incorporating a benzodioxinic subunit: synthesis and complexing ability of sodium and potassium." Canadian Journal of Chemistry 70, no. 3 (March 1, 1992): 828–35. http://dx.doi.org/10.1139/v92-109.

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We report here the synthesis of new polyoxygenated macrocyclic derivatives with a benzodioxinic subunit and a carboxylic side chain (2, 3), along with some of their corresponding acyclic polyethers (1). Formation constants of sodium and potassium complexes with both the acid and anion forms of these compounds were obtained from potentiometric measurements. The enhancement of both complexing ability and selectivity afforded by the presence of a carboxylic side chain is discussed. Keywords: polyether carboxylic acids, macrocycles, benzo-1,4-dioxin, sodium and potassium complexes, solvent methanol.

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41

Tolbin, Alexander Yu, Victor E. Pushkarev, Evgeny V. Shulishov, and Larisa G. Tomilova. "Directed synthesis of bi- and polynuclear clamshell-type phthalocyanines and their physico-chemical investigations." Journal of Porphyrins and Phthalocyanines 16, no. 04 (April 2012): 341–50. http://dx.doi.org/10.1142/s108842461250037x.

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Novel bi-, tri- and tetranuclear butyl- and tert-butyl-substituted clamshell-type phthalocyanines were synthesized starting from 2-hydroxyphthalocyanines with quantitative yields. The structures of the obtained compounds were characterized by a complex of NMR spectroscopy and mass spectrometry techniques. Applying electronic absorption spectroscopy (UV-vis) and density functional theory (DFT) showed the complicated conformation equilibria for the spacer-bonded macrocyclic compounds and led us to estimate their behavior dependent on the number and relative orientation of macrocycles.

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42

Mandl, Christian, Manfred Zabel, and Burkhard König. "Synthesis and Structure of New Macrocyclic Bisindolylmaleimides." Collection of Czechoslovak Chemical Communications 68, no. 5 (2003): 899–906. http://dx.doi.org/10.1135/cccc20030899.

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We report synthesis and structure of three new macrocyclic bisindolylmaleimides. The UV spectra of the xylene-bridged compounds4and6show significant differences. A dependence of the absorption properties on the maleimide-indole torsion angles is likely. A first attempt to use induced changes in ring conformation of the more flexible macrocyclic crown ether derivative8to signal the presence of metal cations failed.

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43

Lu, Wei, and Charles J. Sih. "Chemoenzymatic synthesis of macrocyclic polyamines." Tetrahedron Letters 40, no. 27 (July 1999): 4965–68. http://dx.doi.org/10.1016/s0040-4039(99)00954-5.

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44

Tamm, Christoph, and Nicolas Jeker. "Synthesis of macrocyclic trichothecene mycotoxins." Tetrahedron 45, no. 8 (January 1989): 2385–415. http://dx.doi.org/10.1016/s0040-4020(01)83438-4.

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45

Guo, Zhi Wei, and Charles J. Sih. "Enzymic synthesis of macrocyclic lactones." Journal of the American Chemical Society 110, no. 6 (March 1988): 1999–2001. http://dx.doi.org/10.1021/ja00214a073.

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46

Shi, Zhen, and Jian-hua Wang. "Synthesis of Dibridged Macrocyclic Tetraazaparacyclophanes." Synthetic Communications 27, no. 13 (July 1997): 2235–39. http://dx.doi.org/10.1080/00397919708003376.

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47

Mehta, Barun, Dandela Rambabu, Guttikonda Raja, ASG Prasad, Jim-Min Fang, and Mandava Rao. "Synthesis of Novel Macrocyclic Tetraamides." Letters in Drug Design & Discovery 11, no. 6 (May 31, 2014): 756–61. http://dx.doi.org/10.2174/1570180811666140116215724.

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48

Williams, Alvin S. "The Synthesis of Macrocyclic Musks." Synthesis 1999, no. 10 (October 1999): 1707–23. http://dx.doi.org/10.1055/s-1999-3581.

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49

Sharghi, Hashem, and Hossein Eshghi. "Efficient synthesis of macrocyclic diamides." Tetrahedron 51, no. 3 (January 1995): 913–22. http://dx.doi.org/10.1016/0040-4020(94)00980-9.

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50

Mulay, Sandip V., Or Dishi, Yuan Fang, Muhammad R. Niazi, Linda J. W. Shimon, Dmitrii F. Perepichka, and Ori Gidron. "A macrocyclic oligofuran: synthesis, solid state structure and electronic properties." Chemical Science 10, no. 37 (2019): 8527–32. http://dx.doi.org/10.1039/c9sc03247a.

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The first π-conjugated macrocyclic system with an oligofuran backbone display planar conformation and forms large π-aggregates, in contrast to the twisted conformation of small macrocyclic oligothiophenes.

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