应用化学2017，Vol.34Issue(7)：757-767,11.DOI:10.11944/j.issn.1000-0518.2017.07.160419
由α-氰基肉桂酸乙酯/N-溴代苯甲酰胺合成2-噁唑啉衍生物
Synthesis of 2-Oxazoline Derivatives from Ethyl α-Cyanocinnamate Derivatives and N-Bromobenzamide
摘要
Abstract
2-Oxazoline derivative belongs to an important class of heterocyclic compounds, new synthetic method and new 2-oxazoline derivatives are eagerly desired.In order to develop a new protocol for the synthesis of deferent structural 2-oxazoline derivatives, a method from ethyl α-cyanocinnamate derivatives and N-bromobenzamide has been explored.The structures of all eleven synthesized products were confirmed by proton nuclear magnetic resonance spectroscopy(1H NMR), and mass spectrometry(MS).The results show that a series of ethyl α-cyanocinnamate derivatives(3a~3k) can be smoothly converted into corresponding 2-oxazoline derivatives(5a~5k).When Na2CO3 was used as the promoter in acetone at room temperature, the corresponding products were obtained in high yield(up to 90%).Not only can ethyl α-cyanocinnamate derivatives be used as substrate, but also ethyl α-carbethoxy-cyanocinnamate(6) can be employed as the substrate, too.Experiment results indicate that N-bromo-p-nitrobenzamide(8) and N-bromoacetamide(9) can tolerate this reaction except N-bromobenzamide(4).Above results indicate that the easy and efficient protocol has application in a large scope of electron-deficient olefins and N-bromoamide.A possible mechanism was proposed which can explain well the full regiospecificity of the reaction.关键词
α-氰基肉桂酸乙酯/N-溴本甲酰胺/噁唑啉衍生物Key words
ethyl α-cyanocinnamate/N-bromobenzamide/oxazoline derivative分类
化学化工引用本文复制引用
惠文萍,刘德娥,侯丹,陈战国..由α-氰基肉桂酸乙酯/N-溴代苯甲酰胺合成2-噁唑啉衍生物[J].应用化学,2017,34(7):757-767,11.基金项目
国家自然科学基金(20572066)、陕西省自然科学基金(2009JM2011)和陕西师范大学研究生创新基金(2008CXB009)资助 （20572066）
Supported by the National Natural Science Foundation of China(No.20572066), the Natural Science Foundation of Shaanxi Province(No.2009JM2001), the Innovation Foundation of Postgraduate Cultivation of Shaanxi Normal University(No.2008CXB009) （No.20572066）
