Premium
Synthesis of benzothiophene analogues of ketoconazole and itraconazole
Author(s) -
Bolós Jordi,
Gilbert Santiago,
Anglada Lluis,
Sacristan Aurelio,
Ortiz José A.
Publication year - 1997
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.5570340611
Subject(s) - chemistry , ketoconazole , benzothiophene , itraconazole , enamine , stereochemistry , antifungal , thiophene , organic chemistry , catalysis , medicine , dermatology
The synthesis of the benzothiophene analogues of the orally active antifungal agents ketoconazole and itraconazole 3a and 3b is reported. The key heterocyclic system 3‐(1‐piperazinyl)benzo[ b ]thiophene is prepared by formation of the enamine between a benzothienone and ethyl 1‐piperazinecarboxylate. After elaboration of the respective N ‐substituents, the methoxy group is cleaved with boron tribromide, and O ‐alky‐1ated with the corresponding mesylates.