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
收稿日期: 2016-03-18
修回日期: 2016-04-22
网络出版日期: 2016-05-06
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
Received date: 2016-03-18
Revised date: 2016-04-22
Online 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).
陈战国 , 侯丹 , 刘德娥 , 惠文萍 . 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[J]. 有机化学, 2016 , 36(9) : 2191 -2196 . DOI: 10.6023/cjoc201603032
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
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