Acryl Activation by Intramolecular Hydrogen Bond: Morita Baylis Hillman Reaction of Acrylamide with Broad Substrate Scope

摘要

Use of acrylamide as an activated alkene in largely recognized Morita Baylis Hillman (MBH) reaction has been least explored owing to less reactivity of acrylamide as Michael acceptor. Contrary acrylamide have profound applications in synthetic, medicinal and polymer chemistry. An intramolecular Hydrogen bond activated, MBH reaction of N-(2-hydroxyphenyl) acrylamide has been developed. With various control experiments, role of ortho hydroxy was found to be as an activator and was critical for success of reaction. Under the influence of DABCO, designed acrylamides gave wide substrate scope including a number of less reactive aldehydes and chemo selective MBH reactions. Such mode of activation can be helpful in design of other reactions too. An example has been presented by successful Michael addition reaction.