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
收藏
页码：2894 / 2898
页数：5
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