One-pot synthesis of highly functionalized 1,2-dihydropyridines from primary alkylamines, alkyl isocyanides, and acetylenic esters

Yavari, Issa; Bayat, Mohammad; Sirouspour, Mehdi; Souri, Sanaz

doi:10.1016/j.tet.2010.08.016

Cited by 58 publications

(24 citation statements)

References 14 publications

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“…1,2 MCRs are particularly useful to generate diverse chemical libraries of drug-like molecules for biological screening. 3 A broad spectrum of biological activity have been reported for dihydropyrimidinones and pyridazine derivatives.…”

Section: Introductionmentioning

confidence: 99%

The first practical approach to new pyrimido[4,5-d]pyridazines: novel chemoselective and regioselective reactions

Karami

Akrami²,

Khodabakhshi³

et al. 2013

Arkivoc

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A new three-component condensation of aryl glyoxals, acetylacetone and urea in the presence of a small amounts of tungstate sulfuric acid (TSA) leads to novel functionalized 5-acetyl-4-(aryloyl)-3,4-dihydropyrimidinones which these heterocycles can undergo the Knorr condensation with hydrazines to produce new pyrimido [4,5-d]pyridazines in good yields. These approaches are consistent with principles of green chemistry due to some factors, such as the use of a safe and recyclable catalyst under solvent-free conditions.

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Section: Introductionmentioning

confidence: 99%

The first practical approach to new pyrimido[4,5-d]pyridazines: novel chemoselective and regioselective reactions

Karami

Akrami²,

Khodabakhshi³

et al. 2013

Arkivoc

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“…Yavari, et al 17 has reported one pot synthesis of highly functionalized 1,2-dihydropyridines from alkyl isocyanide 60a-b, acetylenic esters 61a-b and primary alkylamine (62a-i). The reaction of alkyl isocyanides 60a-b, dimethyl acetylenedicarboxylate (61a), and primary amines 57a, 62a-h, proceeded smoothly in CH 2 Cl 2 at room temperature and produced tetramethyl 4-(alkylamino)-1-alkyl(aryl)-1,2-dihydropyridine-2,3,5,6-tetracarboxylates 63a-k in good yields aer purication (Scheme 17).…”

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confidence: 99%

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

2017

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Dihydropyridine (DHP) is among the most beneficial scaffolds that have revolutionised pharmaceutical research with unprecedented biological properties. Over the years, metamorphosis of easily accessible 1,2-and 1,4-dihydropyridine (1,4-DHP) intermediates by synthetic chemists has generated several drug molecules and natural products such as alkaloids. The 1,4-dihydropyridine (1,4-DHP) moiety itself is the main fulcrum of several approved drugs. The present review aims to collate the literature of 1,2-and the 1,4-DHPs relevant to synthetic and medicinal chemists. We will describe various methodologies that have been used for the synthesis of this class of compounds, including the strategies which can furnish enantiopure DHPs, either by asymmetric synthesis or by chiral resolution.We will also elaborate the significance of DHPs towards the synthesis of natural products of medicinal merit.

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“…5,6 One-pot MCRs continue to be of interest in the synthesis of heterocyclic compounds owing to the fast assembly of the same without the isolation of unstable intermediates. [7][8][9][10] Hence, the production of biologically active heterocycles by means of MCRs has attracted significant attention over the past decades. 11,12 The combination of pyrrolidines or pyrrolizidines with spirooxindole ring systems provides the central skeletons for numerous alkaloids and pharmacologically important compounds.…”

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confidence: 99%

Synthesis of new bis-spirooxindolopyrrolizidine(pyrrolidine) derivatives via a pseudo five-component 1,3-dipolar cycloaddition reaction

Taghizadeh

Javidan

Keshipour

2015

Chem Heterocycl Comp

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One-pot synthesis of highly functionalized 1,2-dihydropyridines from primary alkylamines, alkyl isocyanides, and acetylenic esters

Cited by 58 publications

References 14 publications

The first practical approach to new pyrimido[4,5-d]pyridazines: novel chemoselective and regioselective reactions

The first practical approach to new pyrimido[4,5-d]pyridazines: novel chemoselective and regioselective reactions

Synthesis, utility and medicinal importance of 1,2- & 1,4-dihydropyridines

Synthesis of new bis-spirooxindolopyrrolizidine(pyrrolidine) derivatives via a pseudo five-component 1,3-dipolar cycloaddition reaction

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