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| 三氟亚乙基取代的N-苯甲酰基氮杂环丙烷的合成 | |
| 引用本文： | 吴伟,黄焰根,卿凤翎.三氟亚乙基取代的N-苯甲酰基氮杂环丙烷的合成[J].有机化学,2009,29(8):1249-1253. |
| 作者姓名： | 吴伟 黄焰根 卿凤翎 |
| 作者单位： | 1. 东华大学化学化工与生物工程学院,上海,201620 2. 东华大学化学化工与生物工程学院,上海,201620;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 |
| 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, 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 |
| 收稿时间： | 2009-3-22 |
| 修稿时间： | 2009-4-29 |
Syntheses of Trifluoroethylidene Substituted N-Benzoyl Aziridines |
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| Wu Wei,Huang Yangen,Qing Fengling.Syntheses of Trifluoroethylidene Substituted N-Benzoyl Aziridines[J].Chinese Journal of Organic Chemistry,2009,29(8):1249-1253. | |
| Authors: | Wu Wei Huang Yangen Qing Fengling |
| Institution: | (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) |
| Abstract: | 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. |
| Keywords: | trifluoroethylidene aziridine ring opening reaction |
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