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Journal articles on the topic 'Heterocyclic compounds. Stereoisomers'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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1

Adeeva, Valeriya G., Marina S. Bobyleva, Nickolay S. Kulikov, Valentina G. Kharchenko, and Lev M. Yudovich. "Gas chromatography—mass spectrometry of the stereoisomers of heterocyclic compounds. Part 1. Perhydrothioxanthenes." J. Chem. Soc., Perkin Trans. 2, no. 6 (1992): 965–69. http://dx.doi.org/10.1039/p29920000965.

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2

Bobyleva, Marina S., and Nickolay S. Kulikov. "Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 2a.1 Perhydroxanthenes." Journal of the Chemical Society, Perkin Transactions 2, no. 4 (1998): 951–54. http://dx.doi.org/10.1039/a706142k.

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3

Kulikov, Nickolay S., and Marina S. Bobyleva. "Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 2b.1 Perhydroxanthenes." Journal of the Chemical Society, Perkin Transactions 2, no. 4 (1998): 955–58. http://dx.doi.org/10.1039/a706143i.

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4

BOBYLEVA, M. S., and N. S. KULIKOV. "ChemInform Abstract: Gas Chromatography-Mass Spectrometry of the Stereoisomers of Heterocyclic Compounds. Part 2a. Perhydroxanthenes." ChemInform 29, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199831024.

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5

KULIKOV, N. S., and M. S. BOBYLEVA. "ChemInform Abstract: Gas Chromatography-Mass Spectrometry of the Stereoisomers of Heterocyclic Compounds. Part 2b. Perhydroxanthenes." ChemInform 29, no. 31 (2010): no. http://dx.doi.org/10.1002/chin.199831025.

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6

Kulikov, Nickolay S., and Marina S. Bobyleva. "Gas chromatography–mass spectrometry of the stereoisomers of heterocyclic compounds. Part 3.† Perhydro-4-thia-s-indacene." Journal of the Chemical Society, Perkin Transactions 2, no. 3 (2000): 571–76. http://dx.doi.org/10.1039/a904941j.

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7

Sparr, Christof, and Christian Fischer. "Configurationally Stable Atropisomeric Acridinium Fluorophores." Synlett 29, no. 16 (2018): 2176–80. http://dx.doi.org/10.1055/s-0037-1610233.

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Arylated heterocyclic fluorophores are particularly useful scaffolds for numerous applications, such as bioimaging or synthetic photochemistry. While variation of the substitution pattern at the heterocycle and aryl groups allows dye modulation, the bond rotational barriers are also strongly affected. Unsymmetrically substituted ring systems of rotationally restricted arylated heterocycles therefore lead to configurationally stable atropisomeric fluorophores. Herein, we describe these characteristics by determining the properties and configurational stability of atropisomeric, tri-ortho-substi

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8

Żesławska, Ewa, Anna Jakubowska, and Wojciech Nitek. "Conformational study of the 3,6-dihydro-2H-1,4-oxazin-2-one fragment in 8-tert-butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decane-2,10-dione stereoisomers." Acta Crystallographica Section C Structural Chemistry 73, no. 7 (2017): 556–62. http://dx.doi.org/10.1107/s2053229617009068.

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Unnatural cyclic α-amino acids play an important role in the search for biologically active compounds and macromolecules. Enantiomers of natural amino acids with a D configuration are not naturally encoded, but can be chemically synthesized. The crystal structures of two enantiomers obtained by a method of stereoselective synthesis, namely (5R,8S)-8-tert-butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decane-2,10-dione, (1), and (5S,8R)-8-tert-butyl-7-methoxy-8-methyl-9-oxa-6-azaspiro[4.5]decane-2,10-dione, (2), both C14H21NO4, were determined by X-ray diffraction. Both enantiomers crystallize i

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9

Bhagat, S., P. Kumari, N. Sharma, A. Kumar, and S. Mohapatra. "A Highly Efficient Approach for the Synthesis of Novel Trifluoroacetylated Enaminones using DBU as a Base." Synlett 28, no. 15 (2017): 2008–13. http://dx.doi.org/10.1055/s-0036-1588865.

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An efficient methodology has been developed for the synthesis of a variety of novel trifluoroacetylated enaminones by using trifluoroacetic anhydride in DCE as solvent and DBU as a base via electrophilic trifluoroacetylation. X-ray crystallographic studies confirmed the trifluoroacetylation and E stereoisomeric form of the novel compounds. The synthetic strategy has the advantage of using an inexpensive and non-toxic base for producing excellent yields. Synthons bearing variety of functional groups may be further extended for the formation of heterocyclic compounds.

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10

Merouani, Hafida, Christophe Morell, Nadia Ouddai, and Henry Chermette. "DFT study of the stereo-selectivity of oxygenated heterocycles from 10 to 12 links." Canadian Journal of Chemistry 91, no. 9 (2013): 811–20. http://dx.doi.org/10.1139/cjc-2012-0521.

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Intra-molecular Diels–Alder (IMDA) reactions of tethered trienes can furnish two distinct diastereoisomeric products, the cis (i.e., endo) stereoisomer and the trans (i.e., exo) stereoisomer. Experimental evidence shows a quite high cis stereo-selectivity for 10-link compounds (cis/trans = 70:30), while 11- and 12-links compounds exhibit no particular selectivity. DFT (B3LYP/6-31G*) computations provide useful insights into the origins of this amazing stereo-selectivity. The cyclization path towards trans stereo-isomer is always thermodynamically favored, whatever the size of the system. The h

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11

Reznikov, Alexander N., Dmitry S. Nikerov, Anastasiya E. Sibiryakova, Victor B. Rybakov, Evgeniy V. Golovin, and Yuri N. Klimochkin. "Convenient access to pyrrolidin-3-ylphosphonic acids and tetrahydro-2H-pyran-3-ylphosphonates with multiple contiguous stereocenters from nonracemic adducts of a Ni(II)-catalyzed Michael reaction." Beilstein Journal of Organic Chemistry 16 (August 25, 2020): 2073–79. http://dx.doi.org/10.3762/bjoc.16.174.

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A new synthetic strategy toward nonracemic phosphoryl-substituted pyrrolidines and tetrahydropyranes with three and five contiguous stereocenters is presented. Readily available β-keto phosphonates react with conjugated nitroolefins in the presence of a chiral Ni(II) complex to give nitro keto phosphonates with two stereocenters with excellent enantioselectivity and moderate to high diastereoselectivity. These products were used for a reductive cyclization leading to pyrrolidin-3-ylphosphonic acid and for reactions with aldehydes yielding tetrahydropyranylphosphonates as individual stereoisome

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12

Breau, L., N. K. Sharma, I. R. Butler, and T. Durst. "Synthesis and X-ray crystal structure determination of 3,4-diphenyl-6-(diphenylmethyl)-1,5-dioxa-2-thiane-2-oxide." Canadian Journal of Chemistry 69, no. 2 (1991): 185–88. http://dx.doi.org/10.1139/v91-029.

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Erythro and threo-1,2-diphenyl-2-tert-butylsulfinylethanols 5 and 8 were prepared from the condensation of the α-lithio derivative of benzyl-tert-butyl sulfoxide with benzaldehyde. Reaction of 5 with sulfuryl chloride gave the title compound, (2R*,3S*,4R*,6R*)-3,4-diphenyl-6-(diphenylmethyl)-1,5-dioxa-2-thiane-2-oxide 6, the first representative of a new heterocyclic ring system. Similar treatment of 8 resulted in the formation of 7, a stereoisomer of 6. This same compound was also obtained by photolysis of 6. In both 6 and 7 the S=O bond is in an axial orientation. Key words: sulfuryl chlorid

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13

Bringmann, Gerhard, Doris Feineis, Wael Saeb, Christiana Hesselmann, Eva-Maria Peters, and Karl Peters. "Endogenous Alkaloids in Man, Part 33. Dimethyl (2S,4S)-and (2R,4S)-5,5-Dimethyl-1,3-thiazolidine-2,4-dicarboxylates, Two Diastereomeric Glyoxylate-Derived Heterocycles." Zeitschrift für Naturforschung B 55, no. 2 (2000): 208–12. http://dx.doi.org/10.1515/znb-2000-0213.

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Both title compounds were obtained in stereochemically pure form by refluxing 5,5-dim ethyl-1 ,3-thiazolidine-2,4-dicarboxylic acid (3) with methanolic HCl, followed by a separation of the two diastereomers 4a and 4b on silica gel. The X-ray structure analyses of these stereoisomers confirm the relative configuration to be cis for 4a and trans for 4b with respect to the two carboxymethyl substituents at C(2) and C(4). For both molecules, an envelopetype conformation of the thiazolidine ring was found with C(5)-S(1)-C(2)-N(3) being located in a plane showing a small ring torsion angle of -11.2°

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14

González-Romero, Carlos, Pablo Bernal, Fabiola Jiménez, et al. "Conjugate systems in the construction of heterocycles and quaternary stereocenters." Pure and Applied Chemistry 79, no. 2 (2007): 181–91. http://dx.doi.org/10.1351/pac200779020181.

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The synthetic application of 4,5-bis-alkylidene-1,3-oxazolidin-2-ones led to the efficient and regioselective synthesis of 2-(3H)-benzoxazolones and diarylamines with a short methodology. They were also valuable synthons in a total synthesis of naturally occurring carbazoles. New enantiopure 4-oxazoline-2-one and 4-methylene-2-oxazolidinone were prepared via a one-pot microwave (MW)-promoted condensation of α-ketols and an enantiopure isocyanate. These enamides were efficient nucleophiles when added to Michael acceptors to give a series of compounds with quaternary stereocenters in fairly good

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15

Dembitsky, V. M., G. A. Tolstikov та M. Srebnik. "Boranes in Organic Chemistry 2. β-Aminoalkyl- and β-sulfanylalkylboranes in organic synthesis". Eurasian Chemico-Technological Journal 4, № 3 (2017): 153. http://dx.doi.org/10.18321/ectj528.

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<p>Problems on using of β-aminoalkyl- and β-sulfanylalkylboranes in organic synthesis are considered in this review. The synthesis of boron containing a-aminoacids by Curtius rearrangement draws attention. The use of β-aminoalkylboranes available by enamine hydroboration are described. Examples of enamine desamination with the formation of alkenes, aminoalcohols and their transformations into allylic alcohol are presented. These conversions have been carried out on steroids and nitrogen containing heterocyclic compounds. The dihydroboration of N-vinyl-carbamate and N-vinyl-urea have been

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16

Braune, Annett, Michael Gütschow, and Michael Blaut. "An NADH-Dependent Reductase from Eubacterium ramulus Catalyzes the Stereospecific Heteroring Cleavage of Flavanones and Flavanonols." Applied and Environmental Microbiology 85, no. 19 (2019). http://dx.doi.org/10.1128/aem.01233-19.

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ABSTRACT The human intestinal anaerobe Eubacterium ramulus is known for its ability to degrade various dietary flavonoids. In the present study, we demonstrate the cleavage of the heterocyclic C-ring of flavanones and flavanonols by an oxygen-sensitive NADH-dependent reductase, previously described as enoate reductase, from E. ramulus. This flavanone- and flavanonol-cleaving reductase (Fcr) was purified following its heterologous expression in Escherichia coli and further characterized. Fcr cleaved the flavanones naringenin, eriodictyol, liquiritigenin, and homoeriodictyol. Moreover, the flava

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17

Li Petri, Giovanna, Maria Valeria Raimondi, Virginia Spanò, Ralph Holl, Paola Barraja, and Alessandra Montalbano. "Pyrrolidine in Drug Discovery: A Versatile Scaffold for Novel Biologically Active Compounds." Topics in Current Chemistry 379, no. 5 (2021). http://dx.doi.org/10.1007/s41061-021-00347-5.

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AbstractThe five-membered pyrrolidine ring is one of the nitrogen heterocycles used widely by medicinal chemists to obtain compounds for the treatment of human diseases. The great interest in this saturated scaffold is enhanced by (1) the possibility to efficiently explore the pharmacophore space due to sp3-hybridization, (2) the contribution to the stereochemistry of the molecule, (3) and the increased three-dimensional (3D) coverage due to the non-planarity of the ring—a phenomenon called “pseudorotation”. In this review, we report bioactive molecules with target selectivity characterized by

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18

Lee, Hwa-Kyung, Jonghwa Lee, Junghak Lee, Joon-Kwan Moon, and Jeong-Han Kim. "X-ray crystal structure of endosulfan sulfate." Applied Biological Chemistry 62, no. 1 (2019). http://dx.doi.org/10.1186/s13765-019-0466-9.

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Abstract X-ray crystallography is an important method used to confirm the three-dimensional structure of a chemical compound. In this study, the crystal structure of endosulfan sulfate was investigated. Endosulfan sulfate is the major metabolite of the insecticide endosulfan, which is composed of two stereoisomers (α and β). From GC–MS analysis, α- and β-endosulfan each gave a single peak in the endosulfan sample, but only one peak was observed for endosulfan sulfate. Interestingly, in X-ray crystallography, two conformers of endosulfan sulfate (A and B) were observed at a ratio of 2(A):1(B).

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