Facile Synthesis of Perfluoroalkyl Substituted 1,5-Benzodiazepine-2-ones via a Catalyst-free Process

doi:10.6023/cjoc201210037

Chin. J. Org. Chem. ›› 0, Vol. ›› Issue (0): 0-0.DOI: 10.6023/cjoc201210037

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无催化剂条件下的全氟烷基取代的1H-苯并[b][1,4]二氮?-2(3H)-酮的简易合成

翟士燕^a, 曹卫国^a,b,c, 张慧^a

a 上海大学化学系上海 200444;
b 中科院上海有机化学研究所金属有机国家重点开放实验室上海 200032;
c 中科院上海有机化学研究所氟化学重点开放实验室上海 200032

收稿日期:2012-10-19 修回日期:2012-11-18 出版日期:2012-12-31 发布日期:2012-11-23
通讯作者: 曹卫国, 张慧 E-mail:yehao7171@shu.edu.cn; wgcao@staff.shu.edu.cn

Facile Synthesis of Perfluoroalkyl Substituted 1,5-Benzodiazepine-2-ones via a Catalyst-free Process

Zhai Shiyan^a, Cao Weiguo^a,b,c, Zhang Hui^a

a Department of Chemistry, Shanghai University, Shanghai 200444;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
c Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2012-10-19 Revised:2012-11-18 Online:2012-12-31 Published:2012-11-23
Supported by:
Project supported by the National Natural Science Foundation of China (Grant Nos. 21072126 and 21272152) and the Leading Academic Discipline Projects of Shanghai Municipal Education Commission (Grant No. J50102).

Abstract

1,5-Benzodiazepin-2-one is a privileged scaffold and compounds containing such substructures exhibit a range of biological activities. Perfluoroalkyl groups can favorably affect the physical and biological properties of organic compounds. Accordingly, the development of methods to introduce perfluoroalkyl groups into 1,5-benzodiazepin-2-ones has become increasingly important. Herein, an ef?cient and simple route for preparation of perfluoroalkylated 1,5-benzodiazepine-2-ones is described. The reaction of methyl 3-perfluoroalkyl-2-alkynoate as the fluorinated building block with o-arylenediamine proceeds smoothly in dry toluene at 80 ℃ for 24 h without any catalyst to afford the titled compounds in good yields.

Key words: perfluoroalkyl, 1,5-benzodiazepine-2-one, methyl 3-perfluoroalkyl-2-alkynoate, o-arylenediamine

Cite this article

Zhai Shiyan, Cao Weiguo, Zhang Hui. Facile Synthesis of Perfluoroalkyl Substituted 1,5-Benzodiazepine-2-ones via a Catalyst-free Process[J]. Chin. J. Org. Chem., 0, (0): 0-0.

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无催化剂条件下的全氟烷基取代的1H-苯并[b][1,4]二氮?-2(3H)-酮的简易合成

Facile Synthesis of Perfluoroalkyl Substituted 1,5-Benzodiazepine-2-ones via a Catalyst-free Process

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