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Synfacts 2008(8): 0807-0807  
DOI: 10.1055/s-2008-1077943
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Gallium(III) Triflate Catalyzed Synthesis of Quinazolinones from Isatoic Anhydrides

Contributor(s): Victor Snieckus, Jignesh J. Patel
J. Chen, D. Wu, F. He, M. Liu, H. Wu*, J. Ding, W. Su*
Wenzhou University and Zhejiang University of Technology, Hangzhou, P. R. of China
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

A one-pot Lewis acid catalyzed synthesis of 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones from isatoic anhydrides, aromatic aldehydes, and ammonium acetate or primary amines is described. Among various solvents (CH2Cl2, H2O, MeCN, MeNO2) and triflate salts (of Cu, Zn, Mg, Sc and lanthanide metals) which were tested, the combination of EtOH and Ga(OTf)3 was found to be the couple of choice. EtOH as solvent gives A while DMSO acts as a mild oxidant that oxidizes A into B. The scope of the reaction was well tested with respect to the aldehyde but neither to the isatoic anhydride nor the amine component.