Preparation of Quinazolines via a 2+2+2 Annulation from Aryldiazonium Salts and Nitriles

J Org Chem. 2017 Aug 4;82(15):8290-8295. doi: 10.1021/acs.joc.7b01325. Epub 2017 Jul 24.

Abstract

A (2+2+2) modular synthesis of multisubstituted quinazolines has been realized by the direct reaction of aryldiazonium salts with two equivalent of nitriles. Reaction of aryldiazonium salt with a nitrile provides the initial formation of a reactive nitrilium ion, which is attacked by another molecule of nitrile followed by electrophilic cyclization to deliver the desired product. Notable flexibility in the substitution patterns, readily available substrates, short reaction time, transition metal-free, and gram-scale synthesis are the advantages of this method.

Publication types

  • Research Support, Non-U.S. Gov't