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Updated: Jul 14, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Formation of benzo-fused carbocycles by formal radical cyclization onto an aromatic ring
Derrick L J Clive1, Rajesh Sunasee
1Chemistry Department, University of Alberta, Edmonton, Alberta, Canada. derrick.clive@ualberta.ca
Abstract:
An indirect method for effecting radical carbocyclization onto aromatic rings is described. Cross-conjugated dienones such as 13, readily prepared by Birch reduction of aromatic tert-butyl esters, in situ alkylation, and oxidation (10 --> 11 --> 12 --> 13), undergo radical cyclization; the products (14) are aromatized by silylation, Saegusa oxidation, and treatment with BiCl3.H2O. A noteworthy feature of this route is that it provides opportunities to attach an additional substituent to the original aromatic ring.
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