Journal ArticleDOI
Recent developments in multicomponent synthesis of structurally diversified tetrahydropyridines
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TLDR
In this article, a review of the advancement made in the field of multicomponent synthesis of tetrahydropyridines and their derivatives of the last few years is presented.Abstract:
Tetrahydropyridines (THPDs) have been recognized as a major constituent of naturally occurring alkaloids. Being heterocyclic nitrogenous compounds, they therefore display robust biological and pharmacological profiles. In this context, they are fascinating synthetic targets in synthetic chemistry and as a consequence of this their synthesis through simple and convenient tactics has emerged as an important and challenging task. To meet such challenge, multicomponent reactions (MCRs) are employed as an excellent tool for achieving compounds containing complex diversity in single step and production of their vast libraries. This review represents the advancement made in the field of multicomponent synthesis of THPDs and their derivatives of the last few years.read more
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Journal ArticleDOI
Mechanochemical synthesis of small organic molecules.
TL;DR: A collection of examples on recent developments in organic bond formation reactions like carbon–carbon, carbon–nitrogen (C–N), carbon–oxygen (C-O), carbon-halogen (C –X), etc. is documented.
Journal ArticleDOI
Multicomponent Mannich reactions: General aspects, methodologies and applications
João Francisco Allochio Filho,Bárbara C. Lemos,Acácio S. de Souza,Sergio Pinheiro,Sandro J. Greco +4 more
TL;DR: The multicomponent Mannich reaction is a green and classical method for the preparation of β-aminoketones and β-aminoaldehydes (Mannich bases) and, as such, is one of the most important reactions in organic chemistry as discussed by the authors.
Journal ArticleDOI
Heteropolyacid-Containing Ionic Liquid-Catalyzed Multicomponent Synthesis of Bridgehead Nitrogen Heterocycles: Mechanisms and Mitochondrial Staining.
Haline Gerica de Oliveira Alvim,José R. Corrêa,José Antonio Fagundes Assumpção,Wender A. Silva,Marcelo O. Rodrigues,Julio L. de Macedo,Mariana Fioramonte,Fabio C. Gozzo,Claudia C. Gatto,Brenno A. D. Neto +9 more
TL;DR: The current manuscript describes the use of a heteropolyacid-containing task-specific ionic liquid, supported in imidazolium-based ionic liquids, as the catalyst for an efficient multicomponent synthesis of hexahydroimidazo[1,2-α]pyridine derivatives.
Journal ArticleDOI
Mechanistic knowledge and noncovalent interactions as the key features for enantioselective catalysed multicomponent reactions: a critical review
TL;DR: The problems of a lack of mechanistic knowledge and the importance of the rational design of new catalytic systems, considering the possible noncovalent interactions aimed towards designing "flexible" and adaptative catalysts to fit the key intermediates and reagents, are discussed in light of new concepts and trends.
Journal ArticleDOI
Synthesis of functionalized dihydro-2-oxypyrroles and tetrahydropyridines using 2,6-pyridinedicarboxylic acid as an efficient and mild organocatalyst
TL;DR: In this article, simple and efficient protocols have been developed for the synthesis of diversely functionalized dihydro-2-oxypyrroles and tetrahydropyridines.
References
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A facile synthesis and discovery of highly functionalized tetrahydro-pyridines and pyridines as antimycobacterial agents.
Suresh Kumar Raju,Michael Rajesh Stephen,Perumal Subbu,Banerjee Debjani,Yogeeswari Perumal,Sriram Dharmarajan +5 more
TL;DR: Ethyl 2,6-di(2-bromophenyl)-4-hydroxy-5-(phenylsulfanyl)-3-pyridinecarboxylate was found to be the most active with a minimum inhibitory concentration of 1.33 microM against Mycobacterium tuberculosis and is 5.74 and 38.17 times more potent than the first line anti-tuberculosis drugs, ethambutol and pyrazinamide respectively.
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Curare Alkaloids: Constituents of a Matis Dart Poison.
Gonzalo R. Malca Garcia,Lothar Hennig,Irina V. Shelukhina,Denis S. Kudryavtsev,Rainer W. Bussmann,Victor I. Tsetlin,Athanassios Giannis +6 more
TL;DR: A phytochemical study of dart and arrow poison from the Matis tribe led to the identification of D-(-)-quinic acid, L-malic Acid, ethyldimethylamine, magnoflorine, and five new bisbenzyltetrahydroisoquinoline alkaloids (BBIQAs), 1-5, which contains a unique linkage at C-8 and C-11'.
Journal ArticleDOI
Stereochemistry of the 2-hydroxy-1,2,3,4-tetrahydropyridine intermediate of hantzsch cyclization
Toshihisa Ogawa,Keita Matsumoto,Misa Yoshimura,Katsuo Hatayama,Kunihiro Kitamura,Yasuyuki Kita,Yasuyuki Kita +6 more
TL;DR: Hantzsch cyclization of cyanoethyl 3-aminocrotonate and (E,Z)-4-dialkoxymethyl 2-benzylidene-acetoacetates (5a,b) afforded 3,4-trans-2-hydr.
Journal ArticleDOI
Lithium Perchlorate-, Acetic Anhydride-, and Triphenylphosphine-assisted Multicomponent Syntheses of 4-Unsubstituted 2,5-Dioxooctahydroquinoline-3-carboxylates and 3-carbonitriles.
Xingxian Gu,Gunda I. Georg +1 more
TL;DR: Lithium perchlorate and acetic anhydride were the key additives for the multi-component reaction between 3-aminocyclohex-2-enones, formaldehyde, and malonates yielding adducts that were annulated under acidic conditions to afford bicyclic 2,5-dioxooctahydroquinoline-3-carboxylates.
Journal ArticleDOI
Multicomponent reaction design: a one-pot route to substituted di-O-acylglyceric acid amides from α-diazoketones
TL;DR: In this article, a four-component assembly of substituted di-O-acylglyceric acid amides has been developed from α-diazoketones, which involves copper-catalyzed reaction of the α-doroketone with a carboxylic acid, and subsequent Passerini condensation of the in situ formed α-acylsoxyketone.