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

Chun HuangYou ZhouXiao-Xiao YuLi-Sheng WangYan-Dong WuYan-Dong Wu
Published in: The Journal of organic chemistry (2021)
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.
Keyphrases
  • fatty acid
  • ionic liquid
  • high resolution
  • molecularly imprinted
  • mass spectrometry
  • structure activity relationship