A Novel and Efficient Synthesis of 1-Hydroxyquinazolin-4-ones via Tin(II) Chloride Induced Cyclization of 2-Nitrobenzamides and Ketones

Daqing Shi; Guolan Dou; Yao Zhou

doi:10.1055/s-2008-1067126

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Synthesis 2008(13): 2000-2006
DOI: 10.1055/s-2008-1067126

PAPER

A Novel and Efficient Synthesis of 1-Hydroxyquinazolin-4-ones via Tin(II) Chloride Induced Cyclization of 2-Nitrobenzamides and Ketones

Daqing Shi*^a,b, Guolan Dou^b, Yao Zhou^b
^a Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215123, P. R. of China
e-Mail: dqshi@263.net;
^b Department of Chemistry, Xuzhou Normal University, Xuzhou 221116, P. R. of China

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Publication History

Received 27 February 2008
Publication Date:
11 June 2008 (online)

Abstract
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Abstract

A mild, efficient and novel synthesis of 2,3-dihydro-1-hydroxyquinazolin-4(1H)-ones via cyclization of 2-nitrobenzamides and ketones induced by tin(II) chloride dihydrate is described. This new method has the advantages of accessible starting materials, convenient manipulation, short reaction times, and high yields.

Key words

tin(II) chloride dihydrate - 1-hydroxyquinazolin-4-one - 2-nitrobenzamide - ketone

References

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Crystallographic data for the structures of 3a (CCDC-682915), 5b (CCDC-682916), 7e (CCDC-682917), and 9a (CCDC-682918) have been deposited at the Cambridge Crystallographic Data Centre. Copies of available material can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033; email: deposit@ccdc.cam.ac.uk].