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Paper | Regular issue | Vol 71, No. 7, 2007, pp.1589-1600
Published online, 8th May, 2007
DOI: 10.3987/COM-07-11054
Microwave-Assisted Efficient Synthesis of Polymethoxyacetophenones and Natural Polymethoxyflavones, and Their Inhibitory Effects on Melanogenesis

Masao Tsukayama,* Eiji Kusunoki, Mohammad M. Hossain, Yasuhiko Kawamura, and Shinji Hayashi

*Department of Chemical Science and Technology, Faculty of Engineering, University of Tokushima, Minamijosanjima-cho, Tokushima 770-8506, Japan

Abstract

Microwave-assisted Friedel-Crafts acetylation of polymethoxybenzenes with acetic anhydride in the presence of In(CF3SO3)3 under solvent-free conditions was achieved rapidly to give polymethoxyacetophenones in high yields. Microwave-assisted benzoylation of 2’-hydroxypolymethoxyacetophenones with polymethoxybenzoyl chlorides, followed by the rearrangement of the resulting benzoates and the final formation of natural polymethoxyflavones was achieved rapidly and efficiently. The polymethoxyflavones showed inhibitory effects on melanogenesis in human melanoma cells.