Copper-catalyzed ligand-free amidation of aryl iodides and amino acid amides to synthesize C3-(Z)-1H-benzo[e][1,4]diazepin-2(3H)-ones

Mol Divers. 2015 Nov;19(4):695-701. doi: 10.1007/s11030-015-9603-5. Epub 2015 Jun 7.

Abstract

An effective synthetic method for C3-chiral 1,4-benzodiazepine-2-ones is described in this paper, reporting good yields and high enantioselectivity with a novel approach to an ipso-halo displacement-cyclization benzodiazepine route.

Keywords: Amidation; C3-(Z)-1H-benzo[e][1, 4]diazepin-2(3H)-ones; Copper-catalyzed; Cyclization; Diazepinones.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry*
  • Amino Acids / chemistry
  • Benzodiazepines / chemical synthesis*
  • Benzodiazepines / chemistry
  • Copper / chemistry
  • Cyclization
  • Iodides / chemistry*
  • Molecular Structure

Substances

  • Amides
  • Amino Acids
  • Iodides
  • Benzodiazepines
  • Copper