Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation

Sachin D. Gawande, Veerababurao Kavala, Manoj R. Zanwar, Chun Wei Kuo, Wen Chang Huang, Ting Shen Kuo, Hsiu Ni Huang, Chiu Hui He, Ching-Fa Yao

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

An efficient, one-pot method for the synthesis of dibenzodiazepinone derivatives involving copper-catalyzed tandem C-N bond formation is reported. The use of various halo amide and 2-iodoaniline derivatives permitted the synthesis of an array of dibenzodiazepinone derivatives in moderate to good yields. Moreover, a dibenzodiazepinone derivative {2-(11-oxo-5H-dibenzo[b,e][1, 4]diazepin-10(11H)-yl)benzonitrile} was utilized to synthesize the triazapentacyclic ring derivative {12-chloro- 8,15,22-triazapentacyclo[13.7.0. 02,7.09,14.016,21]docosa-1(22),2,4,6,9(14),10, 12,16(21),17,19-decaene}.

Original languageEnglish
Pages (from-to)2599-2608
Number of pages10
JournalAdvanced Synthesis and Catalysis
Volume356
Issue number11-12
DOIs
Publication statusPublished - 2014 Aug 11

Keywords

  • C-N bond formation
  • Ullmann coupling
  • copper catalysts
  • dibenzodiazepinones
  • tandem processes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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    Gawande, S. D., Kavala, V., Zanwar, M. R., Kuo, C. W., Huang, W. C., Kuo, T. S., Huang, H. N., He, C. H., & Yao, C-F. (2014). Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation. Advanced Synthesis and Catalysis, 356(11-12), 2599-2608. https://doi.org/10.1002/adsc.201301020