Diversity-oriented synthesis of 1,3-benzodiazepines

Gaigai Wang, Chao Liu, Binbin Li, Yingchun Wang, Kristof Van Hecke, Erik V. Van der Eycken, Olga P. Pereshivko, Vsevolod A. Peshkov

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A concise assembly of the 1,3-benzodiazepine core from A 3 -coupling-derived propargylamines and ortho-bromophenylisocyanates is described. The developed synthetic sequence involves the addition of propargylamine to isocyanate followed by palladium-catalyzed intramolecular alkyne hydroarylation that could be accomplished in a stepwise or one-pot manner.

Original languageEnglish
Pages (from-to)6372-6380
Number of pages9
JournalTetrahedron
Volume73
Issue number44
DOIs
Publication statusPublished - Nov 2 2017
Externally publishedYes

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Keywords

  • 1,3-Benzodiazepines
  • A -coupling
  • Isocyanates
  • Medium-rings
  • Propargylamines
  • Reductive Heck reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Wang, G., Liu, C., Li, B., Wang, Y., Van Hecke, K., Van der Eycken, E. V., Pereshivko, O. P., & Peshkov, V. A. (2017). Diversity-oriented synthesis of 1,3-benzodiazepines. Tetrahedron, 73(44), 6372-6380. https://doi.org/10.1016/j.tet.2017.09.034