Convenient Synthetic Approach to 2,4-Disubstituted Quinazolines

Serena Ferrini, Fabio Ponticelli, and Maurizio Taddei*
Dipartimento di Chimica and Dipartimento Farmaco Chimico Tecnologico, Universit degli Studi di Siena, Via A. Moro, 53100 Siena, Italy
Org. Lett., 2007, 9 (1), pp 69–72
DOI: 10.1021/ol062540s
Publication Date (Web): December 7, 2006
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, taddei.m@unisi.it

Abstract

Abstract Image

2,4-Dialkyl or aryl quinazolines have been prepared in three steps starting from easily available anilides. A photochemically induced Fries rearrangement of the anilides gave several ortho-aminoacylbenzene derivatives that were acylated at the NH2. These acylamides underwent rapid cyclization to 2,4-disubstituted quinazolines (and benzoquinazolines) in the presence of ammonium formate under microwave activation. This procedure is compatible with different functional groups and allowed also the preparation of new quinazolines derived from naturally occurring amino acids.

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History

  • Published In Issue January 04, 2007
  • Received October 16, 2006

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