Poster Title

Synthesis and Reactivity of 1,3,7,7-Tetramethyl-4H,10H-6,8,9-trioxa-2-thia Benzo[f]azulen-5-one

Institution

Kentucky State University

Abstract

Meldrum’s acid is an attractive substitute to acylic malonate esters in organic synthesis. Monoalkylated malonic acids and esters have found importance in pharmaceuticals as useful organic synthons. Dialkyl Meldrum’s acids are versatile synthetic intermediates and their applications in organic reactions have been well documented. In this study, we performed reaction of two equivalents of Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione, isopropylidene malonate), with one equivalent of 3,4-bis(chloromethyl)-2,5-dimethyl-thiophene or bis(bromomethyl)-2,5- dimethylthiophene which resulted in the kinetically favored O-alkylated product 1,3,7,7-tetramethyl-4H,10H-6,8,9-trioxa-2-thia-benzo[f]azulen-5-one in high yield.

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Synthesis and Reactivity of 1,3,7,7-Tetramethyl-4H,10H-6,8,9-trioxa-2-thia Benzo[f]azulen-5-one

Meldrum’s acid is an attractive substitute to acylic malonate esters in organic synthesis. Monoalkylated malonic acids and esters have found importance in pharmaceuticals as useful organic synthons. Dialkyl Meldrum’s acids are versatile synthetic intermediates and their applications in organic reactions have been well documented. In this study, we performed reaction of two equivalents of Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione, isopropylidene malonate), with one equivalent of 3,4-bis(chloromethyl)-2,5-dimethyl-thiophene or bis(bromomethyl)-2,5- dimethylthiophene which resulted in the kinetically favored O-alkylated product 1,3,7,7-tetramethyl-4H,10H-6,8,9-trioxa-2-thia-benzo[f]azulen-5-one in high yield.