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Short Paper | Special issue | Vol 93, No. 2, 2016, pp.816-823
Published online, 10th December, 2015
DOI: 10.3987/COM-15-S(T)59
Yb(OTf)3-Catalyzed Synthesis of 2-Substituted 4(3H)-Quinazolinones via Cleavage of a Carbon-Carbon Bond

Tsutomu Yoshimura, Shun-ichi Naito, Di Yuanjun, Aoi Son, Yu Kimura, Akio Toshimitsu, and Teruyuki Kondo*

*Advanced Biomedical Engineering Research Unit, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan

Abstract

A general, selective, and practical one-pot synthesis of 2-substituted 4(3H)-quinazolinones by the Yb(OTf)3-catalyzed cyclo-condensation of 2-aminobenzamides with acyclic or cyclic 1,3-diketones (β-diketones) under mild and neutral reaction conditions has been developed, which involves the highly selective cleavage of a C-C bond in 1,3-diketones by Yb(OTf)3 catalyst. For example, the Yb(OTf)3-catalyzed cyclo-condensation of 2-aminobenzamide (1a) with 1-phenylbutane-1,3-dione (2c) gave 2-methyl-4(3H)-quinazolinone (3a) in 90% yield, together with acetophenone in 65% yield. Ring-opening cyclo-condensation of 2-aminobenzamides (1a) with cyclic 1,3-diketones (2i and 2k-m), except for cyclopentane-1,3-dione (2j), gave 2-substitued 4(3H)-quinazolinones (3i and 3k-m) with one carbonyl group.