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Short Paper | Special issue | Vol 95, No. 1, 2017, pp.608-614
Published online, 1st December, 2016
DOI: 10.3987/COM-16-S(S)35
2-Arylquinoline Synthesis from Cbz-Protected 2-Aminochalcone Mediated by BF3•Et2O

Tomohiro Maegawa,* Misa Nogata, Takaya Honda, Akira Nakamura, and Yasuyoshi Miki*

*School of Pharmaceutical Sciences, Kindai University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan

Abstract

A novel approach to producing the quinoline skeleton from 2-aminochalcone was developed. Treatment of benzyloxycarbonyl (Cbz)-protected 2-aminochalcones with BF3·Et2O afforded quinoline derivatives via the deprotection of the Cbz group and isomerization of olefin in a one-pot reaction. The reaction of various 2-aminochalcones proceeded to give the corresponding 2-arylquinoline derivatives in good yields. This method is applicable to the rapid synthesis of dubamine.