Organic Chemistry Portal

Abstracts

Search:

Convenient Synthetic Approach to 2,4-Disubstituted Quinazolines

Serena Ferrini, Fabio Ponticelli and Maurizio Taddei*

*Dipartimento di Chimica and Dipartimento Farmaco Chimico Tecnologico, UniversitÓ degli Studi di Siena, Via A. Moro, 53100 Siena, Italy, Email: taddei.munisi.it

S. Ferrini, F. Ponticelli, M. Taddei, Org. Lett., 2007, 9, 69-72.

DOI: 10.1021/ol062540s (free Supporting Information)


Abstract

A photochemically induced Fries rearrangement of anilides gave several ortho-aminoacylbenzene derivatives that were acylated. These acylamides underwent rapid microwave-assited cyclization to 2,4-disubstituted quinazolines (and benzoquinazolines) in the presence of ammonium formate.

see article for more reactions

see article for more examples

proposed mechanism



Key Words

Quinozalines, Fries Rearrangement, Microwave Synthesis


ID: J54-Y2007-0090