Facile access to 2-aryl-3-nitro-2H-chromenes and 2,3,4-trisubstituted chromanes

被引：12

作者：

Wang, Ping-An ^{[1
]}

Zhang, Dong-Xu ^{[1
]}

Liu, Xue-Ying ^{[1
]}

机构：

[1] Fourth Mil Med Univ, Sch Pharm, Dept Med Chem, Changle Xilu 169, Xian 710032, Peoples R China

来源：

ARKIVOC | 2014年

基金：

美国国家科学基金会;

关键词：

2-aryl-3-nitro-2H-chromene; 2,3,4-trisubstituted chromane; tandem oxa-Michael-Henry reaction; reductive amination; X-ray diffraction analysis; MICHAEL ADDITION-REACTIONS; CONJUGATE ADDITION; ALDEHYDES; CATALYSIS;

D O I：

10.3998/ark.5550190.p008.801

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Using salicylaldehydes and beta-nitrostyrenes as starting materials, 2-aryl-3-nitro-2H-chromenes were prepared in good yields (up to 83%) through the combination of 30 mol% of pyrrolidine-benzoic acid catalyzed tandem oxa-Michael-Henry reactions in refluxing ethanol. Additionally, the Michael reactions of 2-aryl-3-nitro-2H-chromenes with acetone were also performed by the same catalytic combination in brine to give 2,3,4-trisubstituted chromanes up to 86% yield with excellent stereoselectivities. The structures of 2-aryl-3-nitro-2H-chromenes and 2,3,4-trisubstituted chromanes are confirmed by X-ray single crystal diffraction analysis. The reductive amination of a suitable 2,3,4-trisubstituted chromane with Zn/HOAc affords a fused tricyclic amine in 92% yield.

引用

页码：408 / 419

页数：12

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