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

18 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

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Copper
Derivatives
Amides

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Gawande, S. D., Kavala, V., Zanwar, M. R., Kuo, C. W., Huang, W. C., Kuo, T. S., ... 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

Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation. / Gawande, Sachin D.; Kavala, Veerababurao; Zanwar, Manoj R.; Kuo, Chun Wei; Huang, Wen Chang; Kuo, Ting Shen; Huang, Hsiu Ni; He, Chiu Hui; Yao, Ching-Fa.

In: Advanced Synthesis and Catalysis, Vol. 356, No. 11-12, 11.08.2014, p. 2599-2608.

Research output: Contribution to journalArticle

Gawande, SD, Kavala, V, Zanwar, MR, Kuo, CW, Huang, WC, Kuo, TS, Huang, HN, He, CH & Yao, C-F 2014, 'Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation', Advanced Synthesis and Catalysis, vol. 356, no. 11-12, pp. 2599-2608. https://doi.org/10.1002/adsc.201301020
Gawande SD, Kavala V, Zanwar MR, Kuo CW, Huang WC, Kuo TS et al. Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation. Advanced Synthesis and Catalysis. 2014 Aug 11;356(11-12):2599-2608. https://doi.org/10.1002/adsc.201301020
Gawande, Sachin D. ; Kavala, Veerababurao ; Zanwar, Manoj R. ; Kuo, Chun Wei ; Huang, Wen Chang ; Kuo, Ting Shen ; Huang, Hsiu Ni ; He, Chiu Hui ; Yao, Ching-Fa. / Synthesis of dibenzodiazepinones via tandem copper(I)-catalyzed C-N bond formation. In: Advanced Synthesis and Catalysis. 2014 ; Vol. 356, No. 11-12. pp. 2599-2608.
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