An Efficient, One-Pot Regioselective Synthesis of Highly Functionalized Chromen-5-ones and Pyrano[3,2-c]chromen-5-ones via a Tandem Knoevenagel-Michael-Cyclization Sequence

被引：24

作者：

Kamalraja, Jayabal ^{[1
]}

Muralidharan, Doraiswamy ^{[1
]}

Perumal, Paramasivan Thirumalai ^{[1
]}

机构：

[1] Cent Leather Res Inst, CSIR, Div Organ Chem, Madras 600020, Tamil Nadu, India

来源：

SYNLETT | 2012年 / 20期

关键词：

NMSM; Michael addition; regioselectivity; chromenes and pyranochromenes; one-pot synthesis; SOLVENT-FREE CONDITIONS; MULTICOMPONENT REACTIONS; ORGANIC-SYNTHESIS; AQUEOUS-MEDIA; IMINOCOUMARIN DERIVATIVES; 3-COMPONENT SYNTHESIS; ASYMMETRIC-SYNTHESIS; ALPHA-AMINO; HETEROCYCLES; CHROMENES;

D O I：

10.1055/s-0032-1317543

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile, convenient, efficient, and high-yielding regioselective synthesis of a combinatorial library of hitherto unreported highly functionalized chromen-5-ones and pyrano[3,2-c]chromen-5-ones has been developed by one-pot three-component coupling of substituted aromatic aldehydes, dimedone/4-hydroxycoumarin with NMSM in the presence of catalytic amount of piperidine in ethanol medium. This transformation presumably proceeds via domino Knoevenagel condensation-Michael addition-intermolecular cyclization sequence creating three new bonds (two C-C and one C-O) and one stereocenter in a single operation.

引用

页码：2894 / 2898

页数：5