Base-Promoted Synthesis of 2-Aryl Quinazolines from 2-Aminobenzylamines in Water

J Org Chem. 2018 Jul 20;83(14):7423-7430. doi: 10.1021/acs.joc.8b00327. Epub 2018 Apr 19.

Abstract

A transition-metal-free procedure for the synthesis of a highly valuable class of heteroaromatics, quinazolines, was developed by using easily available 2-aminobenzylamines and α,α,α-trihalotoluenes. The transformation proceeded smoothly in the presence of only sodium hydroxide and molecular oxygen in water at 100 °C, furnishing a variety of 2-aryl quinazolines. The crystallization process of the crude reaction mixture for the purification of the solid products circumvents huge solvent-consuming workup and column chromatographic techniques, which make the overall process more sustainable and economical.

Publication types

  • Research Support, Non-U.S. Gov't