L. М. Pevzner, N. P. Stepanova
Feb 1, 2020
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Journal
Russian Journal of General Chemistry
Abstract
Abstract Based on reactions of phosphorylated derivatives of halomethylfuroic acid esters with thioglycolic acid ester in the presence of bases, a method for the synthesis of mono-and bisphosphosphorylated esters of (2-ethoxy-2-oxoethylthio)methyl derivatives of furoic acids, containing an ester group in the position adjacent to the sulfide moiety was developed. Obtained compounds are relatively easily metallized with potassium tert -butylate, but intramolecular cyclization proceeds smoothly only in the case of 5-(diethoxyphosphorylmethyl)-2-(ethoxycarbonylmethylthiomethyl)furan-3-carboxylic acid. The resulting 1,3-dicarbonyl derivative of 7 H -thiopyrano[3,4- b ]furan is hydrolytically unstable, but its enol O -methyl ether is stabile. Alkaline hydrolysis of the latter compound was studied, and it was shown that it proceeds at the ester as well as at the phosphonate group.