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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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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Journal ArticleDOI
Synthesis of fused tetrahydropyrido[2,3-c]coumarin derivatives as potential inhibitors for dopamine d3 receptors, catalyzed by hydrated ferric sulfate
TL;DR: In this paper, furo-and pyrano-tetrahydropyrido[2,3-c]coumarin derivatives were synthesized using one-pot three component reactions between aromatic aldehydes, 3-aminocoumarins and cyclic enol ethers in the presence of 10 mol% hydrated ferric sulphate [Fe2(SO4)3·xH2O] in refluxing acetonitrile.
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The first example of glucose-containing carbene Brønsted acid synthesis and catalysis: efficient synthesis of five substituted tetrahydropyridines
Qiu-ju Zhou,Yu Wan,Xiao-xiao Zhang,Li-zhuo Zhang,Huan Zou,Hao Cui,Sheng-liang Zhou,Hai-ying Wang,Hui Wu +8 more
TL;DR: In this article, β-1-Imidazole-2,3,4,6-tetrasulfonic-D-glucopyranosyl bisulfate ([Bmim-G-(SO 3 H) 4 ] + [HSO 4 ] −, I ) was synthesized for the first time and used as an efficient catalyst to prepare five-substituted tetrahydropyridines via the three-component condensation of aromatic aldehyde, aromatic aniline and ethyl acetoacetate in ethanol
Journal ArticleDOI
Expedient, catalyst-free, three-component synthesis of fused tetrahydropyridines in water
Perumal Vinoth,P. S. Ram Prasad,Thavaraj Vivekanand,C. Uma Maheswari,Subbiah Nagarajan,J. Carlos Menéndez,Vellaisamy Sridharan +6 more
TL;DR: A catalyst-free, three-component reaction between amino alcohols, 1,3-dicarbonyl compounds and α,β-unsaturated aldehydes was developed for the synthesis of fused tetrahydropyridines in water as discussed by the authors.
Journal ArticleDOI
3-(5-Alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridines: a novel class of central nicotinic receptor ligands
TL;DR: A novel class of central nicotinic acetylcholine receptor ligands, 3-(5-alkylamino-4-isoxazolyl)-1,2,5,6-tetrahydropyridine 4a-f, was synthesized, and extended the alkylamino chain beyond one, compound, changed the pharmacological profile of the compounds in an antagonistic direction.
Journal ArticleDOI
Enaminone-Based Three-Component Reactions for the Diastereoselective Synthesis of Fused Tetrahydropyridines
TL;DR: An environmentally benign multicomponent synthetic method has been realized for the diastereoselective construction of fused tetrahydropyridines as discussed by the authors, in the presence of lactic acid in water-ethanol media.