Synthesis of benzothiophene analogues of ketoconazole and itraconazole | Zendy

Bolós Jordi | Zendy; Gilbert Santiago | Zendy; Anglada Lluis | Zendy; Sacristan Aurelio | Zendy; Ortiz José A. | Zendy

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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.

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