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
Faculty Advisor/ Mentor
Kazi Javed
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.
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.