We have presented simple and general methodologies to obtain (Z)-β-amino α-substituted-α,β-unsaturated amides from formamidine with phenoxyacetyl chloride and 2-(phenylthio)acetyl chloride in the presence of triethylamine. Replacement of the dimethylamino group from above compounds with primary and secondary amines generated a set of substituted (Z)-β-amino-α-substituted-α,β-unsaturated amides by both microwave and thermal heating. The reactions generated the Z-isomer only and a mechanism was proposed. The corresponding products have been further studied by palladium catalyzed Suzuki coupling reactions with boronic acids to generate biphenyl amides.

Novel syntheses of (Z)-β-amino α-substituted-α,β-unsaturated amides via rearrangement- replacement and Suzuki reactions

255th National Meeting (2018)

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