Synlett 2014; 25(08): 1127-1131
DOI: 10.1055/s-0033-1340986
letter
© Georg Thieme Verlag Stuttgart · New York

Amberlyst A26 OH as a Recyclable Catalyst for Hydration of Nitriles and ­Water-Based Synthesis of 4(1H)-Quinazolinones from 2-Aminobenzonitrile and Carbonyl Compounds

Fatemeh Tamaddon*
Department of Chemistry, Faculty of Science, Yazd University, Yazd 89195-741, Iran   Fax: +98(351)8210644   eMail: ftamaddon@yazduni.ac.ir
,
Farzaneh Pouramini
Department of Chemistry, Faculty of Science, Yazd University, Yazd 89195-741, Iran   Fax: +98(351)8210644   eMail: ftamaddon@yazduni.ac.ir
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Publikationsverlauf

Received: 22. Dezember 2013

Accepted after revision: 19. Februar 2014

Publikationsdatum:
18. März 2014 (online)


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Abstract

Selective hydration of nitriles to primary amides as well the base-catalyzed synthesis of 2-substituted 4(1H)-quinazolinones via reaction of 2-aminobenzonitrile with carbonyl compounds using macroporous Amberlyst A26 OH in H2O–EtOH is described. The latter reaction proceeds via tandem hydration of 2-aminobenzonitrile, condensation of the in situ generated 2-aminobenzamide with carbonyl compounds, and cyclization of the imine intermediate to give the quinazolinone derivatives.