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: yamaguchi
gifu-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
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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
