Convenient synthesis of some substituted 5-oxonitriles under aqueous conditions: Synthesis of 3,4-dihydro-2H-pyrrole-2-carbonitriles

被引：14

作者：

Tasheva, D. ^{[1
]}

Petrova, A. ^{[1
]}

Simova, S. ^{[2
]}

机构：

[1] Univ Sofia, Dept Chem, Sofia 1164, Bulgaria

[2] Bulgarian Acad Sci, Inst Organ Chem, Sofia, Bulgaria

来源：

SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 22-24期

关键词：

3,4-dihydro-2H-pyrrole-2-carbonitriles; CH-acidic Schiff bases; Michael reaction;

D O I：

10.1080/00397910701572746

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Michael additions of [(diphenylmethylene)amino]acetonitrile (1) to alpha,beta-unsaturated ketones (chalkones) (2) under aqueous conditions allow for the highly diastereoselective synthesis of substituted 2-amino-5-oxonitriles (3). Selective removal of diphenylmethylene protecting group, followed by in situ cyclization, gives 3,5-diaryl-3,4-dihydro-2H-pyrrole-2-carbonitriles (4).

引用

页码：3971 / 3979

页数：9

共 25 条

[1] DIASTEREOSELECTIVE SYNTHESIS OF SUBSTITUTED GLUTAMIC-ACID DERIVATIVES VIA MICHAEL ADDITIONS OF N-[BIS(METHYLTHIO)METHYLENE]GLYCINATES UNDER SOLID-LIQUID PHASE-TRANSFER CATALYSIS [J].