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4‐ and 5‐trifluoromethylimidazoles. Novel cyclization of trifluoroacetylated aldehyde dimethylhydrazones
Author(s) -
Kamitori Yasuhiro,
Hojo Masaru,
Masuda Ryōtichi,
Ohara Seiji,
Kawasaki Kazuyoshi,
Kawamura Yoshihiko,
Tanaka Masakazu
Publication year - 1990
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.5570270303
Subject(s) - chemistry , trifluoromethyl , aldehyde , aryl , toluene , organic chemistry , medicinal chemistry , silica gel , catalysis , alkyl
Thermally induced cyclization reaction of trifluoroacetylated arylaldehyde dimethylhydrazones 1 in refluxing toluene afforded 1‐methyl ‐4 ‐aryl ‐5 ‐trifluoromethylimidazoles 2 in good yields. In contrast thermal cyclization of 1 in the presence of silica gel gave regioisomeric 1‐methyl ‐4 ‐trifluoromethyl ‐5 ‐aryl‐imidazoles 5 as major products. These reactions could be extended to the syntheses of related several 1,4,5‐trisubstituted imidazoles.