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Analogs of propranolol. Synthesis of 3‐alkylamino‐1‐(3‐benzo[ b ]thienyloxy)‐2‐propanols
Author(s) -
Conde Santiago,
Corral Carlos,
Lissavetzky Jaime
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170518
Subject(s) - chemistry , thiophene , hydrolysis , propranolol hydrochloride , hydrochloride , propranolol , stereochemistry , organic chemistry , medicinal chemistry , medicine
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.