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Photoinduced Generation of Acyl Radicals from Simple Aldehydes, Access to 3-Acyl-4-arylcoumarin Derivatives, and Evaluation of Their Antiandrogenic Activities

Kazuki Kawaai, Tomoaki Yamaguchi, Eiji Yamaguchi*, Satoshi Endo, Norihiro Tada, Akira Ikari and Akichika Itoh*

*Laboratory of Pharmaceutical Synthetic Chemistry and Laboratory of Biochemistry, Gifu Pharmaceutical University, 1-25-4, Daigaku-nishi, Gifu 501-1196, Japan, Email: yamaguchigifu-pu.ac.jp, itohagifu-pu.ac

K. Kawaai, T. Yamaguchi, E. Yamaguchi, S. Endo, N. Tada, A. Ikari, A. Itoh, J. Org. Chem., 2018, 83, 1988-1996.

DOI: 10.1021/acs.joc.7b02933 (free Supporting Information)


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Abstract

Photocatalysis enables the construction of 3-acyl-4-arylcoumarins in good yields from simple aldehydes and ynoates in the presence of inexpensive 2-tBu-anthraquinone as catalyst. The reaction proceeds through generation of an acyl radical intermediate, that reacts with ynoate, and then cyclization.

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proposed reaction mechanism



Key Words

coumarins, photochemistry, organocatalysis, BPO


ID: J42-Y2018