I2/CuCl2-Copromoted Formal [4 + 1 + 1] Cyclization of Methyl Ketones, 2-Aminobenzonitriles, and Ammonium Acetate: Direct Access to 2-Acyl-4-aminoquinazolines

J Org Chem. 2021 Dec 3;86(23):16916-16925. doi: 10.1021/acs.joc.1c02096. Epub 2021 Nov 9.

Abstract

We herein report an I2/CuCl2-copromoted diamination of C(sp3)-H bonds for the preparation of 2-acyl-4-aminoquinazolines from methyl ketones, 2-aminobenzonitriles, and ammonium acetate. This reaction features operational simplicity, commercially available substrates, mild reaction conditions, and good functional group compatibility. Mechanistic studies indicate that CuCl2 plays a pivotal role in this transformation. This study uses a methyl group as a novel input to construct 2-acyl-4-aminoquinazoline derivatives for the first time.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates
  • Catalysis
  • Cyclization
  • Ketones*
  • Molecular Structure
  • Nitriles
  • Quinazolines

Substances

  • 4-aminoquinazoline
  • Acetates
  • Ketones
  • Nitriles
  • Quinazolines
  • o-aminobenzonitrile
  • ammonium acetate