Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes.
Acrylamide and aromatic aldehydes were found to undergo the Baylis-Hillman reaction at ambient temperature in an aqueous medium in the presence of a stoichiometric amount of base catalyst, DABCO, to give the corresponding 3-hydroxy-2-methylenepropionamides in 61-99% yield. A faster competing, but reversible, non-Baylis-Hillman reaction was initially observed under the conditions to form N-acylhemiaminals, which later disappeared, as the desired Baylis-Hillman adduct was formed as the major product over an extended period of time (12-48 h). This represents the first demonstration of the Baylis-Hillman reaction of aldehydes with acrylamides, which were thought to be inert under atmospheric pressure and at ambient temperature.
Yu
Chengzhi
C
Department of Pharmaceutical Chemistry, College of Pharmacy, Rutgers, the State University of New Jersey, 160 Frelinghuysen Road, Piscataway, New Jersey 08854-8020, USA.
Hu
Longqin
L
D020106:Acrylamide / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D003903:Deuterium; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D013816:Thermodynamics
D000447:Aldehydes; D020106:Acrylamide; D003903:Deuterium