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Report | Regular issue | Vol 23, No. 6, 1985, pp.1483-1491
Published online, 1st January, 1970
DOI: 10.3987/R-1985-06-1483
Synthesis of Phenolic Metanolites of an Antifugal Imidazole Derivatives (Cloconazole Hydrochloride)

Kimio Takahashi, Sumio Shimizu, and Masaru Ogata*

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan

Abstract

Syntheses of phenolic metabolites of antifungal vinylimidazole derivative 6·HCl (Cloconazole hydrochloride) are described. Phenolic compound 8 was prepared from 2 using selective mono THP protection, followed by imidazolation and deprotection. 10 was synthesized from 12 and spontaneously decomposed to 4 and 19 in acidic methanol. Synthesis of 11 started from 20 via nucleophilic aromatic substitution to introduce an oxygen function at the m-position of the chlorine substituent.