Convenient Synthetic Approach to 2,4-Disubstituted Quinazolines

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...

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Bibliographic Details
Published in:Organic letters 2007-01, Vol.9 (1), p.69-72
Main Authors: Ferrini, Serena, Ponticelli, Fabio, Taddei, Maurizio
Format: Article
Language:English
Subjects:
Anilides - chemistry
Molecular Structure
Quinazolines - chemical synthesis
Quinazolines - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol062540s