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Succesful Baylis Hillman Reaction of Acrylamide with Aromatic Aldehydes

Chengzhi Yu and Longqin Hu*

*Department of Pharmaceutical Chemistry, College of Pharmacy, Rutgers, the State University of New Jersey, 08854-8020, Email: LongHurci.rutgers.edu

C. Yu, L. Hu, J. Org. Chem., 2002, 67, 219-223.

DOI: 10.1021/jo016004j (free Supporting Information)


Abstract

Acrylamide and aromatic aldehydes were found to undergo the Baylis-Hillman reaction at ambient temperature and pressure in an aqueous medium in the presence of a stoichiometric amount of DABCO, to give the corresponding 3-hydroxy-2-methylenepropionamides in excellent yield. A faster, but reversible side reaction gave N-acylhemiaminals, which later disappeared, as the desired Baylis-Hillman adducts were formed as major products over an extended period of time.

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Acrylamide is a weak Michael acceptor



Key Words

Baylis-Hillman Reaction, Amides


ID: J42-Y2002-200