Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes.
Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes.
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DOI：
10.1021/jo016004j
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发表时间：
2002-01
期刊：
影响因子：
--
通讯作者：
Chengzhi Yu;Longqin Hu
中科院分区：
文献类型：
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作者：
Chengzhi Yu;Longqin Hu
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.
