Three-Component Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Amides and N-Bromosuccinimide

被引：2

作者：

Chen, Zhanguo ^{[1
]}

Hou, Dan ^{[1
]}

Liu, De'e ^{[1
]}

Hui, Wenping ^{[1
]}

机构：

[1] ShaanxiNormal Univ, Sch Chem & Chem Engn, Key Lab Macromol Sci Shaanxi Prov, Xian 710119, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 36卷 / 09期

基金：

中国国家自然科学基金;

关键词：

2-oxazoline; ethyl alpha-cyanocinnamate; amide; N-bromosuccinimide; K3PO4-CATALYZED REGIOSPECIFIC AMINOBROMINATION; CHIRAL NITRIDOMANGANESE COMPLEX; BETA-NITROSTYRENE DERIVATIVES; ONE-POT SYNTHESIS; STEREOSELECTIVE AMINOBROMINATION; CARBOXYLIC-ACIDS; ELECTROPHILIC DIAMINATION; OXAZOLINES; OLEFINS; EFFICIENT;

D O I：

10.6023/cjoc201603032

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An easy and efficient new method for the three-component synthesis of 2-oxazolines from ethyl alpha-cyanocinnamate derivatives with amide and N-bromosuccinimide has been developed. A series of ethyl alpha-cyanocinnamate derivatives can be smoothly converted into corresponding 2-oxazoline derivatives promoted by Na2CO3 in N,N-dimethylformamide (DMF) at room temperature in high yield (up to 94%). The reactions of 11 structurally different substrates with propionamide, acrylamide, isobutyamide and pentanamide were investigated, respectively. The results indicated that the protocol has applicability in a large scope of ethyl a-cyanocinnamate derivatives and amides. A possible mechanism was proposed and it can explain well the full regiospecificity of the reaction. 39 new compounds were achieved via the three-component synthesis reaction and all the products structures were confirmed by their H-1 NMR, C-13 NMR and HRMS analysis.

引用

页码：2191 / 2196

页数：6

共 53 条

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