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

8 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

Fingerprint

Benzodiazepines
Isocyanates
Alkynes
Palladium
propargylamine

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., ... 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

Diversity-oriented synthesis of 1,3-benzodiazepines. / Wang, Gaigai; Liu, Chao; Li, Binbin; Wang, Yingchun; Van Hecke, Kristof; Van der Eycken, Erik V.; Pereshivko, Olga P.; Peshkov, Vsevolod A.

In: Tetrahedron, Vol. 73, No. 44, 02.11.2017, p. 6372-6380.

Research output: Contribution to journalArticle

Wang, G, Liu, C, Li, B, Wang, Y, Van Hecke, K, Van der Eycken, EV, Pereshivko, OP & Peshkov, VA 2017, 'Diversity-oriented synthesis of 1,3-benzodiazepines', Tetrahedron, vol. 73, no. 44, pp. 6372-6380. https://doi.org/10.1016/j.tet.2017.09.034
Wang G, Liu C, Li B, Wang Y, Van Hecke K, Van der Eycken EV et al. Diversity-oriented synthesis of 1,3-benzodiazepines. Tetrahedron. 2017 Nov 2;73(44):6372-6380. https://doi.org/10.1016/j.tet.2017.09.034
Wang, Gaigai ; Liu, Chao ; Li, Binbin ; Wang, Yingchun ; Van Hecke, Kristof ; Van der Eycken, Erik V. ; Pereshivko, Olga P. ; Peshkov, Vsevolod A. / Diversity-oriented synthesis of 1,3-benzodiazepines. In: Tetrahedron. 2017 ; Vol. 73, No. 44. pp. 6372-6380.
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