One-Pot Synthesis of Trifluoromethylated Quinazolin-4(3 H)-ones with Trifluoroacetic Acid as CF3 Source

J Org Chem. 2018 May 4;83(9):5104-5113. doi: 10.1021/acs.joc.8b00389. Epub 2018 Apr 12.

Abstract

A novel and convenient one-pot sequential cascade method for the preparation of 2-trifluoromethylquinazolin-4(3 H)-ones is described. Trifluoroacetic acid (TFA) was employed as inexpensive and readily available CF3 source, which in the presence of T3P was condensed with a variety of anthranilic acids and amines to provide the products in up to 75% yield. The protocol was proved to be robust on 80 g scale, and the synthetic versatility of the prepared quinazolinon-4-ones was demonstrated by derivatization to further useful building blocks.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Methylation
  • Quinazolines / chemical synthesis*
  • Quinazolines / chemistry*
  • Trifluoroacetic Acid / chemistry*

Substances

  • Quinazolines
  • Trifluoroacetic Acid