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

doi:10.6023/cjoc201603032

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (9): 2191-2196.DOI: 10.6023/cjoc201603032 Previous Articles Next Articles

ARTICLE

α-氰基肉桂酸乙酯/酰胺/N-溴代丁二酰亚胺三组分合成2-噁唑啉

陈战国, 侯丹, 刘德娥, 惠文萍

陕西师范大学化学化工学院陕西省大分子科学实验室西安 710119

收稿日期:2016-03-18 修回日期:2016-04-22 发布日期:2016-05-06
通讯作者: 陈战国 E-mail:chzhg@snnu.edu.cn
基金资助:
国家自然科学基金（No.20572066）、陕西省自然科学基金（No.2009JM2001）、陕西师范大学研究生创新基金（No.2008CXB009）资助项目.

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

Chen Zhanguo, Hou Dan, Liu De'e, Hui Wenping

Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Chemical Engineering, ShaanxiNormal University, Xi'an 710119

Received:2016-03-18 Revised:2016-04-22 Published:2016-05-06
Supported by:
Project supported by the National Natural Science Foundation of China (No.20572066), the Natural Science Foundation of Shaanxi Province (No.2009JM2001) and the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University (No.2008CXB009).

1. Three-Component Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Amides and N-Bromosuccinimide.PDF(1578KB)

Abstract

An easy and efficient new method for the three-component synthesis of 2-oxazolines from ethyl α-cyanocinnamate derivatives with amide and N-bromosuccinimide has been developed. A series of ethyl α-cyanocinnamate derivatives can be smoothly con-verted 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 α-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 ¹H NMR, ¹³C NMR and HRMS analysis.

Key words: 2-oxazoline, ethyl α-cyanocinnamate, amide, N-bromosuccinimide

Cite this article

Chen Zhanguo, Hou Dan, Liu De'e, Hui Wenping. Three-Component Synthesis of 2-Oxazolines from Ethyl α-Cyanocinnamate Derivatives with Amides and N-Bromosuccinimide[J]. Chin. J. Org. Chem., 2016, 36(9): 2191-2196.

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α-氰基肉桂酸乙酯/酰胺/N-溴代丁二酰亚胺三组分合成2-噁唑啉

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

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