Intercepted-Knoevenagel condensation for the synthesis of unsymmetrical fused-tricyclic 4H-pyrans

被引：6

作者：

Shearer, Charles ^{[1
]}

Desaunay, Oriane ^{[1
]}

Zorc, Stephen ^{[1
]}

Richaud, Alexis D. ^{[1
]}

Samanta, Shyam S. ^{[1
]}

Jeedimalla, Nagalakshmi ^{[1
]}

Roche, Stephane P. ^{[1
]}

机构：

[1] Florida Atlantic Univ, Dept Chem & Biochem, Boca Raton, FL 33431 USA

来源：

TETRAHEDRON | 2019年 / 75卷 / 43期

关键词：

Intercepted-Knoevenagel condensation; Multicomponent reaction; 4H-pyrans; Domino reaction; Hydrogen-bond network; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; SOLVENT-FREE; POLYHYDROQUINOLINE DERIVATIVES; 3-COMPONENT SYNTHESIS; HANTZSCH REACTION; IONIC LIQUID; EFFICIENT SYNTHESIS; PHASE SYNTHESIS; 1,4-DIHYDROPYRIDINES;

D O I：

10.1016/j.tet.2019.130606

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4H-Pyrans (4H-Pys) and 1,4-dihydropyridines (1,4-DHPs) are important classes of heterocyclic scaffolds in medicinal chemistry. Herein, an indium(III)-catalyzed one-pot domino reaction for the synthesis of highly functionalized 4H-Pys, and a model of 1,4-DHP is reported. This alternative approach to the challenging Hantzsch 4-component reaction enables the synthesis of fused-tricyclic heterocycles, and the mechanistic studies underline the importance of an intercepted-Knoevenagel adduct to achieve higher chemoselectivity towards these types of unsymmetrical heterocycles. Published by Elsevier Ltd.

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页数：12

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