Selenium-Catalyzed Carbonylative Synthesis of 3,4-Dihydroquinazolin-2(1 H)-one Derivatives with TFBen as the CO Source

ACS Comb Sci. 2019 Aug 12;21(8):573-577. doi: 10.1021/acscombsci.9b00090. Epub 2019 Jul 23.

Abstract

An efficient and general carbonylative procedure for the synthesis of 3,4-dihydroquinazolin-2(1H)-one from 1-(halomethyl)-2-nitrobenzenes and aryl/alkyl amines have been explored. In this approach, to avoid of using toxic CO gas, a solid and stable CO precursor, TFBen (benzene-1,3,5-triyl triformate), was utilized. With elemental selenium as the catalyst, a variety of aryl/alkyl amines has been tolerated well to afford the corresponding 3,4-dihydroquinazolin-2(1H)-one products in moderate to excellent yields under mild reaction condition.

Keywords: benzene-1,3,5-triyl triformate; carbonylative procedure; elemental selenium; heterocycle synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene Derivatives / chemistry*
  • Carbon Monoxide / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Formates / chemistry*
  • Molecular Structure
  • Quinazolinones / chemical synthesis*
  • Quinazolinones / chemistry
  • Selenium / chemistry*

Substances

  • Benzene Derivatives
  • Formates
  • Quinazolinones
  • benzene-1,3,5-triyl triformate
  • Carbon Monoxide
  • Selenium