Synthesis of Substituted Alkoxythiophenes: Thiophene Analogues of Dazoxiben

摘要

The synthesis of the thiophene analogue of dazoxiben-one of the most selective TXA_2-synthase inhibitors- and its derivatization to a chlorinated, more lipophilic product is described. The ethylenoxy moiety was introduced via nucleophilic aromatic substitution of halogenated thiophene carboxylic esters, the imidazol residue, by use of a t-butoxy group as a synthon after ether cleavage and halogenation. Also, at this step chlorination of the thiophene moiety was carried out. After ester hydrolysis the target compounds were obtained as hydrochlorides.