Relevant bibliographies by topics / Heterocyclic compounds. Stereochemistry

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Academic literature on the topic 'Heterocyclic compounds. Stereochemistry'

Author: Grafiati
Published: 4 June 2021
Last updated: 30 January 2023

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Journal articles on the topic "Heterocyclic compounds. Stereochemistry"

1

Perlmutter, Patrick. "The Nucleophilic Addition/Eiectrophilic Ring Closure Route to Bio-Active Heterocycles." Current Medicinal Chemistry 3, no. 2 (April 1996): 139–52. http://dx.doi.org/10.2174/092986730302220302101738.

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Abstract: Many bio-active compounds contain one or more saturated or partially saturated heterocycles. Most of these contain one or more stereo­ centres. As a result any attempts to synthesize these compounds must take full account of the stereochemistry. In this article a new approach to the stereoselective synthesis of heterocycles is reviewed. The emphasis is on oxygen-containing heterocycles. The approach involves a sequence of a nucleophilic addition reaction followed by an electrophilic ring closure. Examples are given of the stereoselective synthesis of the heterocyclic subunits of macrolide and polyether antibiotics, y­butyrolactone autoregulators, marine polyether toxins and C-glycosides.
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El-Sonbati, A. Z., A. A. M. Belal, S. I. El-Wakeel, and M. A. Hussien. "Stereochemistry of new nitrogen containing heterocyclic compounds." Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 60, no. 4 (March 2004): 965–72. http://dx.doi.org/10.1016/s1386-1425(03)00326-3.

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Azzena, Ugo, Massimo Carraro, and Luisa Pisano. "Addressing Stereochemistry of Heterocyclic Compounds by DFT NMR Calculations." Chemistry of Heterocyclic Compounds 54, no. 4 (April 2018): 380–88. http://dx.doi.org/10.1007/s10593-018-2279-x.

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Larina, Lyudmila I. "The Structure of Biologically Active Functionalized Azoles: NMR Spectroscopy and Quantum Chemistry." Magnetochemistry 8, no. 5 (May 6, 2022): 52. http://dx.doi.org/10.3390/magnetochemistry8050052.

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This review summarizes the data on the stereochemical structure of functionalized azoles (pyrazoles, imidazoles, triazoles, thiazoles, and benzazoles) and related compounds obtained by multipulse and multinuclear 1H, 13C, 15N NMR spectroscopy and quantum chemistry. The stereochemistry of functionalized azoles is a challenging topic of theoretical research, as the correct interpretation of their chemical behavior and biological activity depends on understanding the factors that determine the stereochemical features and relative stability of their tautomers. NMR spectroscopy, in combination with quantum chemical calculations, is the most convenient and reliable approach to the evaluation of the stereochemical behavior of, in particular, nitrogen-containing heteroaromatic and heterocyclic compounds. Over the last decade, 15N NMR spectroscopy has become almost an express method for the determination of the structure of nitrogen-containing heterocycles.
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Askri, Sonia, Amal Dbeibia, Chadlia Mchiri, Sarra Boudriga, Michael Knorr, Emmanuel Roulland, Olivier Laprévote, Nathalie Saffon-Merceron, and Rafik Gharbi. "Antimicrobial Activity and In Silico Molecular Docking Studies of Pentacyclic Spiro[oxindole-2,3′-pyrrolidines] Tethered with Succinimide Scaffolds." Applied Sciences 12, no. 1 (December 30, 2021): 360. http://dx.doi.org/10.3390/app12010360.

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Three-component cascade reactions of (E)-3-arylidene-1-methyl-pyrrolidine-2,5-diones, L-valine and various isatin derivatives are described. A series of 17 spiropyrrolidine derivatives with wide structural complexity and diversity have been thus obtained in moderate to excellent yields under mild reaction conditions. The structure and stereochemistry of these N-heterocyclic cycloadducts has been established by spectroscopic techniques and unambiguously confirmed by a single-crystal X-ray diffraction analysis performed on one derivative. UV-visible spectra have been recorded for all new compounds. Furthermore, the synthesized N-heterocyclic compounds have been screened for their in vitro antibacterial and antifungal activities. Several derivatives exhibited moderate to good activities, comparable to those of the known standard drugs Amphotericin B and Tetracycline. Structural activity relationships (SARs) and molecular docking of the most promising derivatives into the binding sites of glucosamine 6-phosphate synthase (GlcN6P) and methionyl-trna-synthetase (1PFV) were also established. Furthermore, pharmacokinetic studies indicate that the heterocycles exhibit acceptable predictive ADMET (absorption, distribution, metabolism, excretion, and toxicity) properties and good drug ability.
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Boudriga, Sarra, Saoussen Haddad, Vikneswaran Murugaiyah, Moheddine Askri, Michael Knorr, Carsten Strohmann, and Christopher Golz. "Three-Component Access to Functionalized Spiropyrrolidine Heterocyclic Scaffolds and Their Cholinesterase Inhibitory Activity." Molecules 25, no. 8 (April 23, 2020): 1963. http://dx.doi.org/10.3390/molecules25081963.

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A novel one-pot [3+2]-cycloaddition reaction of (E)-3-arylidene-1-phenyl-succinimides, cyclic 1,2-diketones (isatin, 5-chloro-isatin and acenaphtenequinone), and diverse α-aminoacids such as 2-phenylglycine or sarcosine is reported. The reaction provides succinimide-substituted dispiropyrrolidine derivatives with high regio- and diastereoselectivities under mild reaction conditions. The stereochemistry of these N-heterocycles has been confirmed by four X-ray diffraction studies. Several synthetized compounds show higher inhibition on acetylcholinesterase (AChE) than butyrylcholinesterase (BChE). Of the 17 synthesized compounds tested, five exhibit good AChE inhibition with IC50 of 11.42 to 22.21 µM. A molecular docking study has also been undertaken for compound 4n possessing the most potent AChE inhibitory activity, disclosing its binding to the peripheral anionic site of AChE enzymes.
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Antus, Sándor, Katalin Gulácsi, László Juhász, Loránd Kiss, and Tibor Kurtán. "Synthesis of naturally occurring o-heterocyclic compounds of biological activity." Pure and Applied Chemistry 76, no. 5 (January 1, 2004): 1025–32. http://dx.doi.org/10.1351/pac200476051025.

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The total synthesis of (−)-cabenegrin A-I was achieved via (−)-6aR,11aR maackiain, which was obtained by optical resolution of racemic maackiain using S-(−)-alpha-methylbenzyl isocyanate. The synthesis of rac-maackiain was performed both with the Heck oxyarylation of 7-benzyloxy-2H-chromene and the BF3OEt2 mediated ring closure of isoflavan-4-ol derivatives, the latter of which provided much higher yields. The first enantioselective synthesis of trans-6aS,11aR-pterocarpan and its conversion to cis-6aS,11aS -ptarocarpan was also presented starting from racemic 2'-benzyloxyflavanone. Their stereochemistry was deduced by circular dichroism (CD) as well as by X-ray analysis of the ketal intermediate.
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Constable, Edwin C., Richard M. Hartshorn, and Catherine E. Housecroft. "1,1′-Biisoquinolines—Neglected Ligands in the Heterocyclic Diimine Family That Provoke Stereochemical Reflections." Molecules 26, no. 6 (March 13, 2021): 1584. http://dx.doi.org/10.3390/molecules26061584.

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1,1′-Biisoquinolines are a class of bidentate nitrogen donor ligands in the heterocyclic diimine family. This review briefly discusses their properties and the key synthetic pathways available and then concentrates upon their coordination behaviour. The ligands are of interest as they exhibit the phenomenon of atropisomerism (hindered rotation about the C1–C1′ bond). A notation for depicting the stereochemistry in coordination compounds containing multiple stereogenic centers is developed. The consequences of the chirality within the ligand on the coordination behaviour is discussed in detail.
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Simoni, Daniele, Riccardo Rondanin, Riccardo Baruchello, Marinella Roberti, Marcello Rossi, Stefania Grimaudo, Natale D'Alessandro, Francesco Paolo Invidiata, and Manlio Tolomeo. "Retinoic acid and analogs as potent inducers of differentiation and apoptosis. New promising chemopreventive and chemotherapeutic agents in oncology." Pure and Applied Chemistry 73, no. 9 (September 1, 2001): 1437–44. http://dx.doi.org/10.1351/pac200173091437.

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In this report we will describe the preparation and the biological activity of a novel class of heterocyclic arotinoids endowed with potent cytotoxic and apoptotic acitivity. Structure­activity relationship studies revealed that the different stereochemistry at the C9 double bond of retinoids seems associated with a different biological activity: potent apoptotic activity for the cis-isomers, whereas differentiating activity for the trans structures. An interesting modified Wittig procedure that allows easily to arotinoids will also be described. The substitution of the alkenyl portion with a more flexible oxymethyl or aminomethyl moiety gave compounds with poor activity, whereas isoxazole-bridged arotinoids allowed compounds active also on multidrug-resistant (MDR) leukemia cell lines.
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HIRTOPEANU, Anca, Cristina FLOREA, and Michaela Dina STANESCU. "Stereochemistry – key role in the rearrangements of dibenzo-C8 and -C9 derivatives." Revue Roumaine de Chimie 66, no. 2 (2021): 105–17. http://dx.doi.org/10.33224/rrch.2021.66.2.01.

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This paper presents the pioneer research being initiated and conducted by the late Acad. C. D. Nenitzescu and Acad. E. Cioranescu in the Department of Organic Chemistry of the University POLITEHNICA Bucharest, and the Center of Organic Chemistry of the Romanian Academy,. A review of these works seems necessary in order to emphasize the importance of the described researches in their theoretical and practical aspects. The dibenzo-cycloalkanes are compounds with interesting behavior, giving different rearranged products, difficult to obtain by other type of syntheses. The modification of the product stability given by adding a carbon atom is also of interest, the steric factor changing radically the behavior of homologue compounds. The potential biological activity of some of these compounds is important for practical applications. The studied compounds were the subject of several PhD theses of the members of Acad. Cioranescu’s research team. It should also be mentioned that the obtained bridged compounds are raw materials for interesting heterocyclic compounds like the tryptycene analogue prepared in collaboration with Acad. A. T. Balaban.
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Dissertations / Theses on the topic "Heterocyclic compounds. Stereochemistry"

1

Fallah, Asadollah. "Stereochemistry and reactivity of some 1,3-heterocyclic compounds." Thesis, University of Portsmouth, 1989. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.328185.

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Luque, Corredera Carlos. "Asymmetric Synthesis of Decahydroquinolines via Organocatalysis: Total Synthesis of (+)-Lycoposerramine Z and (-)-Cermizine B." Doctoral thesis, Universitat de Barcelona, 2014. http://hdl.handle.net/10803/307218.

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1) En primer lloc s’ha desenvolupat una metodologia general per a la síntesi diastereoselectiva de 5-oxodecahidroquinolines mitjançant una reacció one-pot d’anel·lació de Robinson / reacció aza-Michael intramolecular, que permet obtenir el nucli de decahidroquinolina en un sol pas des d’un beta-cetoèster aquiral i acíclic. Aquesta metodologia, no només permet la formació de cis-decahidroquinolines (tipus A i B), sinó que també dóna accés als corresponents isòmers trans-decahidroquinolínics (tipus C i D) . 2) S’ha dissenyat una versió asimètrica de la metodologia desenvolupada per així tenir accés als diferents nuclis decahidroquinolínics enantiopurs per mitjà de organocatàlisis. El mètode ha estat optimitzat després de realitzar estudis de dissolvents, temperatures i catalitzadors. Aquest building block ha estat aplicat a la síntesis total de l’alcaloide licoposerramina Z, el qual s’ha sintetitzat de forma ràpida i eficient (10 etapes, 20% rendiment global). 3) L’aplicació de l’estratègia coneguda com “pot economy” a una síntesis formada per una sèrie de reaccions tàndem pot ser una solució en quant eficiència dels processos i economització de recursos i temps. S’ha realitzat la primera síntesi de l’alcaloide cermizina B de manera eficient i obtenint un gram de producte natural emprant un total de 8 hores treballades en el transcurs de 10 dies naturals. 4) La metodologia descrita no només és aplicable als nuclis decahidroquinolínics conduents a la síntesi d’alcaloides flegmarina, sinó que també pot conduir als altres alcaloides de la familia Lycopodium, completant així una síntesi biomimètica de tots aquests compostos de forma anàloga de com ho fa la natura. A més, la metodologia es pot extrapol·lar a altres tipus de nuclis (morfans o octahidroindols) emprant petites variacions en els materials de partida (així com variacions de número de carbonis en els materials de partida, o l’ instal·lació del nitrògen en el donador o acceptor de Michael)
1) The treatment of a tert-butyl beta-keto ester tethered to an omega-amino monoprotected group with crotonaldehyde using LiOH as the base, furnishes domino reactions involving the consecutive formation of two C-C bonds and one C-N bond in a sequence that comprises an intermolecular Michael process, followed by intramolecular aldol and aza-Michael reactions. This general methodology for the diastereoselective synthesis of 5-oxodecahydroquinolines implies a biscyclization and the formation of three stereocontrolled stereogenic centres in a single operational step. The resulting cis-decahydroquinoline of type A (arising from the dealkoxycarbonylation reaction) allows, through thermodynamic controlled processes, access to all other relative stereochemistries, providing a set of valuable building blocks (decahydroquinolines of Type B, C, and D). 2) The asymmetric Robinson annulation / intramolecular aza-Michael reaction leading to decahydroquinolines in a single step, from an achiral and acyclic simple beta-keto ester, is not feasible using the classical reaction conditions developed by Jørgensen to synthesize cyclohexenones. After the initial organocatalyzed Michael addition, treatment with acid to promote the dealkoxycarbonylation and intramolecular aldol reaction failed, probably due to the presence of the nucleophilic nitrogen atom in the structure. In contrast, if LiOH is added after the organocatalysis step, the Robinson annulation and the following azacyclization take place in very good yield. The method has been optimized after screenings for the solvent, temperature, additives and catalysts. The resulting decahydroquinoline building block has been used in the total synthesis of the phlegmarine alkaloid lycoposerramine Z, which has been efficiently synthesized: 10 steps and 20% overall yield. 3) A potent solution for the problematic stop-and-go procedure, in which it is necessary to stop the synthesis after each operational step to carry out the work-up and purification of intermediates, is the combination of pot economy strategy and tandem reactions. Following this alternative strategy, we have developed an efficient synthesis of the alkaloid cermizine B via an uninterrupted sequence of 7 reactions, which allowed 1 gram of the natural product to be synthesized, employing 8-12 h of operational time over 10 days. 4) The scope of the strategy developed in the experimental studies carried out in the present PhD Thesis has been extended and applied to other research projects. Thus, the described methodology is not only applicable to the decahydroquinoline nucleus for the total synthesis of phlegmarine alkaloids, but can also be potentially applied to the synthesis of other members of the Lycopodium family. Furthermore, the method can also provide access to other nitrogen-containing heterocycles such as morphans or octahydroindoles with some structural changes in the starting materials (such as the number of carbon atoms in the initial beta-keto ester or the installation of the nitrogen atom in the Michael acceptor or in the donor).
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Dumas, Françoise. "Approches stéréoselectives d'antibiotiques de type carbapénème, thiénamycine et dérivés : contrôle relatif des centres asymétriques, construction du squelette bicyclique." Paris 6, 1987. http://www.theses.fr/1987PA066686.

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Books on the topic "Heterocyclic compounds. Stereochemistry"

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Fallah, Asadollah. Stereochemistry and reactivity of some 1,3-heterocyclic compounds. Portsmouth: PortsmouthPolytechnic, Dept. of Chemistry, 1989.

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Holte, P. ten, I. N. N. Namboothiri, Peter Metz, A. Hassner, and U. Nubbemeyer. Stereoselective Heterocyclic Synthesis III. Springer London, Limited, 2007.

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Metz, Peter. Stereoselective Heterocyclic Synthesis Iii. Springer, 2010.

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P, Metz, ed. Stereoselective heterocyclic synthesis. Berlin: Springer, 1997.

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P, Metz, ed. Stereoselective heterocyclic synthesis. Berlin: Springer, 1999.

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Metz, Peter. Stereoselective Heterocyclic Synthesis I. Edited by Peter Metz. SPRINGER-VERLAG, 1997.

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Katritzky, Alan R. Advances in Heterocyclic Chemistry, Volume 75 (Advances in Heterocyclic Chemistry). Academic Press, 1999.

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Advances in Heterocyclic Chemistry, Volume 75 (Advances in Heterocyclic Chemistry). Academic Press, 1999.

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(Contributor), A. Hassner, P. ten Holte (Contributor), I.N.N. Namboothiri (Contributor), U. Nubbemeyer (Contributor), S. D. Rychnovsky (Contributor), C. J. Sinz (Contributor), B. Zwanenburg (Contributor), and Peter Metz (Editor), eds. Stereoselective Heterocyclic Synthesis 3 (Topics in Current Chemistry). Springer, 2001.

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Advances in Heterocyclic Chemistry. Academic Press, 1987.

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Book chapters on the topic "Heterocyclic compounds. Stereochemistry"

1

Ahluwalia, V. K. "Stereochemistry of Some Heterocyclic Compounds." In Stereochemistry of Organic Compounds, 447–75. Cham: Springer International Publishing, 2022. http://dx.doi.org/10.1007/978-3-030-84961-0_16.

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Romers, C., C. Altona, H. R. Buys, and E. Havinga. "Geometry and Conformational Properties of Some Five- and Six-Membered Heterocyclic Compounds Containing Oxygen or Sulfur." In Topics in Stereochemistry, 39–97. Hoboken, NJ, USA: John Wiley & Sons, Inc., 2007. http://dx.doi.org/10.1002/9780470147139.ch2.

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