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An Effective Method To Prepare Imines from Aldehyde, Bromide/Epoxide, and Aqueous Ammonia

Jing-Mei Huang*, Jue-Fei Zhang, Yi Dong and Wen Gong

*School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640, People's Republic of China, Email: chehjmscut.edu.cn

J.-M. Huang, J.-F. Zhang, Y. Dong, W. Gong, J. Org. Chem., 2011, 76, 3511-3514.

DOI: 10.1021/jo102455q (free Supporting Information)


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Abstract

A mild three-component reaction of aromatic aldehydes, alkyl bromides, and aqueous ammonia as the nitrogen source gives imines in very good yields. The reaction conditions are compatible with a range of functional groups. The reaction of aldehydes and aqueous ammonia with epoxides leads to imines bearing a vicinal hydroxyl group regioselectively.

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Key Words

Imines, Alkylation, Multicomponent Reactions


ID: J42-Y2011-1310