| Abstract: | The synthesis by two alternative routes of 1-(3-benzo[b]thienyloxy)-3-isopropylamino-2-propanol hydrochloride ( 1a HCl), a thiophenic isoster of Propranolol, and related compounds, is reported. The protecting and enolizing properties of the 2-methoxycarbonyl group on benzo[b]thiophene-3-one, along with its facile removal, are utilized in the first route. In the second one, conversion of 3-bromobenzo[b]thiophene in 1-(3-benzo[b]thienyloxy)-2,3-o-isopropylidenepropane is the key step. On the other hand, hydrolysis of 1-(3-benzo[b]furanyloxy)-2,3-o-isopropylidenepropane to the corresponding diol, in order to obtain a furanic isoster of Propranolol (17a ), was unsuccessful. |
