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Gallium(III) Triflate Catalyzed Synthesis of Quinazolinonesfrom Isatoic Anhydrides

DOI

23

Citations

0

References

2008

Year

Jie Chen, Deng-Ze Wu, Mingxin Liu, Haihong Wu, Jian Ding, Weiping Su
Synfacts

Abstract

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.