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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (08): 1249-1253. 上一篇    下一篇

研究论文

三氟亚乙基取代的N-苯甲酰基氮杂环丙烷的合成

吴 伟a ; 黄焰根a; 卿凤翎*,a,b   

  1. (a东华大学化学化工与生物工程学院 上海 201620)
    (b中国科学院上海有机化学研究所有机氟化学重点实验室 上海 200032)
  • 收稿日期:2009-03-22 修回日期:2009-04-29 发布日期:2009-08-30
  • 通讯作者: 卿凤翎

Syntheses of Trifluoroethylidene Substituted N-Benzoyl Aziridines

Wu, Weia; Huang, Yangen a; Qing, Fengling*,a,b   

  1. (a College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620)
    (b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences,
    Shanghai 200032)
  • Received:2009-03-22 Revised:2009-04-29 Published:2009-08-30
  • Contact: Qing, Fengling

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被引次数

1

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, 1H NMR, 19F NMR, MS, HRMS和元素分析进行确证.

关键词: 三氟甲基, 氮杂环丙烷, 开环反应

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.

Key words: aziridine, ring opening reaction, trifluoroethylidene