Synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with acetamide and N-bromosuccinimide

被引：13

作者：

Chen Zhan-guo ^{[1
]}

Xia Wei ^{[1
]}

Wen Hua ^{[1
]}

Wang Dan ^{[1
]}

Li Ya-nan ^{[1
]}

Hu Jun-li ^{[1
]}

机构：

[1] Shaanxi Normal Univ, Sch Chem & Chem Engn, Key Lab Macromol Sci Shaanxi Prov, Xian 710062, Peoples R China

来源：

CHEMICAL RESEARCH IN CHINESE UNIVERSITIES | 2013年 / 29卷 / 04期

基金：

中国国家自然科学基金;

关键词：

One-pot synthesis; Oxazoline; Acetamide; N-Bromosuccinimide(NBS); Regioselectivity; Nucleophilic addition-cyclization; ONE-POT SYNTHESIS; K3PO4-CATALYZED REGIOSPECIFIC AMINOBROMINATION; CHIRAL NITRIDOMANGANESE COMPLEX; BETA-NITROSTYRENE DERIVATIVES; STEREOSELECTIVE AMINOBROMINATION; CARBOXYLIC-ACIDS; OXAZOLINES; OLEFINS; LIGANDS; AMINOHALOGENATION;

D O I：

10.1007/s40242-013-2420-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An efficient method for the one-pot synthesis of 2-oxazolines from ethyl alpha-cyanocinnamate derivatives with acetamide and N-bromosuccinimide(NBS) in the presence of K3PO4 was developed. The reaction was performed smoothly and cleanly to give 2-oxazolines in good to excellent yields(up to 95%) in acetone at room temperature. Thirteen examples were investigated and the results indicated that a large range of alpha-cyanocinnamate derivatives could be suitable for this method. Based on the outcomes of experiment, a possible consecutive nucleophilic addition-cyclization pathway was proposed.

引用

页码：699 / 705

页数：7

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