Facile Synthesis of Perfluoroalkyl Substituted 1H-Benzo[b][1,4]- diazepine-2(3H)-ones via a Catalyst-Free Process

doi:10.6023/cjoc201210037

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 615-620.DOI: 10.6023/cjoc201210037 Previous Articles Next Articles

无催化剂条件下的全氟烷基取代的1H-苯并[b][1,4]二氮(艹卓)-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 中国科学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 中国科学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 发布日期:2012-11-23
通讯作者: 张慧 E-mail:yehao7171@shu.edu.cn; wgcao@staff.shu.edu.cn
基金资助:
国家自然科学基金(Nos. 21072126, 21272152)、上海市教育委员会重点学科建设资金(No. J50102)资助项目.

Facile Synthesis of Perfluoroalkyl Substituted 1H-Benzo[b][1,4]- diazepine-2(3H)-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 Published:2012-11-23
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21072126, 21272152) and the Leading Academic Discipline Projects of Shanghai Municipal Education Commission (No. J50102).

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 efficient 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 1H-Benzo[b][1,4]- diazepine-2(3H)-ones via a Catalyst-Free Process[J]. Chin. J. Org. Chem., 2013, 33(03): 615-620.

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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(艹卓)-2(3H)-酮的简易合成

Facile Synthesis of Perfluoroalkyl Substituted 1H-Benzo[b][1,4]- diazepine-2(3H)-ones via a Catalyst-Free Process

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