摘要
发展了一种制备三氟亚乙基取代的N-苯甲酰基氮杂环丙烷的新颖方法.三氟甲基取代的炔丙胺化合物1在盐酸作用下脱去叔丁基亚磺酰基得到三氟甲基炔丙胺盐酸盐2,当用NaOH作碱对2进行苯甲酰化反应时意外地以中等产率获得了N-苯甲酰基-2-三氟亚乙基氮杂环丙烷类化合物3a～3c.在类似条件下也可以从1出发采用"一锅法"制得氮杂环丙烷3d和3e.化合物3b可以在酸催化下发生开环反应得到化合物6b.化合物3和6的结构经IR,1HNMR,19FNMR,MS,HRMS和元素分析进行确证.
A novel method for preparation of trifluoroethylidene substituted N-benzoyl aziridine compounds was developed. Trifluoromethylated propargyl sulfinamides （1） were converted to trifluoromethylated propergylamine hydrochloride 2 via acidic cleavage of the tert-butanesulfinyl groups. N-Benzoyl-2-trifluoroethylideneaziridines 3a-3c were surprisingly obtained in moderate yields by the ben- zoylation reaction of 2 when using NaOH as base. Aziridines 3d-3e can also be obtained in a one pot process starting from propargyl sulfinamides 1.3b can undergo ring opening reaction under acidic condition to afford compound 6b. The structures of products 3 and 6 were confirmed by IR, 1H NMR, 19F NMR, MS spectra and elemental analyses.
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2009年第8期1249-1253,共5页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(Nos.20832008,20672020)资助项目
关键词
三氟亚乙基
氮杂环丙烷
开环反应
trifluoroethylidene
aziridine
ring opening reaction
