Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes

Chengzhi Yu, Longqin Hu

Research output: Contribution to journalArticlepeer-review

103 Scopus citations

Abstract

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 reverible, 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.

Original languageEnglish (US)
Pages (from-to)219-223
Number of pages5
JournalJournal of Organic Chemistry
Volume67
Issue number1
DOIs
StatePublished - Jan 11 2002

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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