Journal of Organic Chemistry 2011-09-02

K2CO3-promoted domino reactions: construction of functionalized 2,3-dihydrobenzofurans and clofibrate analogues.

Qu-Bo Li, Fei-Ting Zhou, Zheng-Geng Liu, Xue-Feng Li, Wei-Dong Zhu, Jian-Wu Xie

Index: J. Org. Chem. 76(17) , 7222-8, (2011)

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Abstract

The K(2)CO(3)-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.