A novel synthesis of cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzo[b]thien-2-yl]methyl]1h-imidazole. A new class of azole antifungal agents

Ring contraction of cis-3-bromo-7-chloro-3,4-dihydro-2H-1-benzothiopyran-4-ol 4 in the presence of imidazole results in formation of cis-6-chloro-2,3-dihydro-2-(1H-imidazol-1-ylmethyl) benzo[b]thiophene-3-ol 8 as the major product. The structure of 8 was defined unequivocally by X-ray analysis of a solvated (ethyl acetate) and an unsolvated crystal form. Alkylation of 8 with 3-(bromomethyl)-2-chlorothiophene gave cis-1-[[6-chloro-3-[(2-chloro-3-thienyl)methoxy]-2,3-dihydrobenzor[b] thien-2-yl]methyl]lH-imidazole 9, a representative of a new class of azole antifungal agents. © 1988.

Duke Scholars

Author Andrew T. McPhail Chemistry