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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 03: 615 - 620

DOI: https://doi.org/10.6023/cjoc201210037

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

  • Zhai Shiyan ,
  • Cao Weiguo ,
  • Zhang Hui
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  • 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 date: 2012-10-19

  Revised date: 2012-11-18

  Online 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).

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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 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]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 615 -620 . DOI: 10.6023/cjoc201210037

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