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K2CO3-Promoted Domino Reactions: Construction of Functionalized 2,3-Dihydrobenzofurans and Clofibrate Analogues

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posted on 02.09.2011, 00:00 by Qu-Bo Li, Fei-Ting Zhou, Zheng-Geng Liu, Xue-Feng Li, Wei-Dong Zhu, Jian-Wu Xie
The K2CO3-catalyzed domino reactions (Michael alkylation, Mannich alkylation, and aldol alkylation) of salicylic aldehyde derivatives (2-hydroxyaryl-α,β-unsaturated ketones, 2-hydroxyarylnitroalkenes, 2-hydroxyarylimines, and salicylic aldehydes) and 2-halo-1,3-dicarbonyl compounds (diethyl α-bromomalonate, diethyl α-chloromalonate, ethyl 2-chloroacetoacetate, and 3-chloropentane-2,4-dione) were carried out under mild conditions to provide a series of functionalized 2,3-dihydrobenzofurans in moderate to excellent yields. The novel transformations simultaneously gave a series of clofibrate analogues, which possess various substitution patterns.