SYNTHESIS OF BENZOTHIOPHENE ANALOGS OF KETOCONAZOLE AND ITRACONAZOLE

Authors
BOLOS J GUBERT S ANGLADA L SACRISTAN A ORTIZ JA
Citation
J. Bolos et al., SYNTHESIS OF BENZOTHIOPHENE ANALOGS OF KETOCONAZOLE AND ITRACONAZOLE, Journal of heterocyclic chemistry, 34(6), 1997, pp. 1709-1713
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
34
Issue
6
Year of publication
1997
Pages
1709 - 1713
Database
ISI
SICI code
0022-152X(1997)34:6<1709:SOBAOK>2.0.ZU;2-M
Abstract
The synthesis of the benzothiophene analogues of the orally active ant ifungal agents ketoconazole and itraconazole 3a and 3b is reported. Th e key heterocyclic system 3-(1-piperazinyl)benzo[b]thiophene is prepar ed by formation of the enamine between a benzothienone and ethyl 1-pip erazinecarboxylate. After elaboration of the respective N-substituents , the methoxy group is cleaved with boron tribromide, and O-alkylated with the corresponding mesylates.