INTERACTION OF 4-(ALLYLOXY)-5,6-DIMETHYL-2-(THIOPHEN-2-YL)THIENO[2,3-d]PYRIMIDINE WITH TELLURIUM-CONTAINING ELECTROPHILIC REAGENTS

Abstract

The chemistry of tellurium-containing electrophilic reagents remains less explored and studied compared to other chalcogen-containing electrophiles. This study investigates the interaction of tellurium tetrahalides and p-methoxyphenyltellurium trichloride with 4-(allyloxy)-5,6-dimethyl-2-(thiophen-2-yl)thieno[2,3-d]pyrimidine. It was found that reactions with in situ generated tellurium tetrahalides in glacial acetic acid lead to the formation of adducts with a 1:1 composition of 4-(allyloxy)-5,6-dimethyl-2-(thiophen-2-yl)thieno[2,3-d]pyrimidine-tellurium tetrahalide, confirmed by ¹H NMR spectral data and elemental analysis. Reactions between 4-(allyloxy)-5,6-dimethyl-2-(thiophen-2-yl)thieno[2,3-d]pyrimidine and p-methoxyphenyltellurium trichloride in glacial acetic acid also yielded adducts of an identical composition, indicating that substituting tellurium tetrachlorides with aryl tellurium trichloride does not alter the reaction’s outcome. Experimental data demonstrate that the nature of the electrophilic reagent does not affect the reaction path, enabling regioselective formation of 1:1 substrate-electrophile adducts.