Sequential assembly via Michael addition of 2-(triazolyl)acrylates

Abstract The enhanced reactivity of 2-(1,2,3-triazol-1-yl)acrylic acid esters is demonstrated in the consecutive reactions of 2-azidoacrylates by copper-catalyzed azide–alkyne cycloaddition followed by Michael addition. When using aliphatic amines for the Michael addition to 2-(1,2,3-triazol-1-yl)acrylates, we found that the retro-Michael reaction took place in the purification with silica gel. Hydrolysis of the 2-(triazolyl)propiolic acid esters obtained by Michael addition and subsequent condensation enabled us to synthesize a variety of functionalized amides.