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Paper | Regular issue | Vol 78, No. 12, 2009, pp.3023-3036
Published online, 28th September, 2009
DOI: 10.3987/COM-09-11815
Bifunctional Organocatalyst to Promote the Biginelli Reaction under Mild Conditions

Nobuyuki Mase,* Daisuke Nakamura, Yasuhiro Kawano, Yuka Suzuki, and Kunihiko Takabe*

*Department of Molecular Science, Faculty of Engineering, Shizuoka University, 3-5-1 Johoku, Hamamatsu 432-8561, Shizuoka, Japan

Abstract

Binaphthyl compounds, which include a pyridinium ion moiety as an acid and pyridine moiety as a base, have been synthesized and evaluated as bifunctional organocatalysts for the three-component Biginelli reaction. 3,3'-(2,2'-Dimethoxy-1,1'-binaphthyl-3,3'-diyl)dipyridine in the presence of equimolar amount of methanesulfonic acid catalyzed the Biginelli reaction to give the desired product in up to 79% yield even at 25 °C.