Diversity-oriented synthesis of 1,3-benzodiazepines

A concise assembly of the 1,3-benzodiazepine core from A3-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. © 2017 Elsevier Ltd

Authors
Wang G.1 , Liu C.1 , Li B.1 , Wang Y.1 , Van Hecke K. , Van Der Eycken E.V. , Pereshivko O.P.1 , Peshkov V.A.1
Journal
Tetrahedron
Number of issue
44
Language
English
Pages
6372-6380
Status
Published
Link
External link
DOI
10.1016/J.TET.2017.09.034
Volume
73
Year
2017
Organizations
  • 1 College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, China
  • 2 XStruct, Department of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281-S3, Ghent, B-9000, Belgium
  • 3 Laboratory for Organic & Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, 3001, Belgium
  • 4 Peoples Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya Street, Moscow, 117198, Russian Federation
Keywords
1,3-Benzodiazepines; A3-coupling; Isocyanates; Medium-rings; Propargylamines; Reductive Heck reaction
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