

SYNTHESIS OF THIENO[2,3-b]PYRROLE-2(4)-CARBOXYLIC AND 2,4-DICARBOXYLIC ACIDS

Abstract
1-Substituted 5-chloro-4-formylpyrrole-3-carboxylates reacted with thioglycolic acid or ethyl thioglycolate in EtOH containing EtONa at room temperature, forming 4-(ethoxycarbonyl)thieno[2,3-b]pyrrole-2-carboxylic acids or thieno[2,3-b]pyrrole-2,4-dicarboxylates. Cyclocondensation with thioglycolic acid upon refluxing in K2CO3–DMF system was accompanied by decarboxylation and led to the formation of thieno[2,3-b]pyrrole-4-carboxylates. Hydrolysis of the obtained carboxylates with LiOH provided thieno[2,3-b]pyrrole-2(4)-carboxylic and 2,4-dicarboxylic acids.
Keywords
5-chloro-4-formylpyrrole-3-carboxylates, ethyl thioglycolate, thieno[2,3-b]pyrrolecarboxylates, thieno[2,3-b]pyrrolecarboxylic acids, thioglycolic acid, alkaline hydrolysis, cyclocondensation.
Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv