S. A. Sokov, I. Odin, S. S. Zlotskii
Oct 1, 2020
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Journal
Russian Journal of Organic Chemistry
Abstract
Three-component reaction of dimethyl malonate with α,β-acetylenic aldehydes and cyclic secondary amines (pyrrolidine, piperidine, morpholine, and piperazine) under mild conditions afforded dimethyl 2-(3-aminoprop-2-en-1-ylidene)malonates in 50–91% yields. The products were formed preferentially as E isomers, and the described reaction provides a convenient method for the synthesis of push–pull buta-1,3-dienes that are interesting as fluorescent, solvatochromic, and nonlinear optical materials and starting compounds in the synthesis of carbo- and heterocycles. A plausible reaction mechanism involves Knoevenage condensation of dimethyl malonate with α,β-acetylenic aldehyde to give dimethyl 2-(prop-2-yn-1-ylidene)malonate and subsequent nucleophilic addition of cyclic amine to the latter.