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A novel synthesis of 2‐(disubstituted amino)‐5(4)phenylimidazoles
Author(s) -
Nishimura Tamio,
Nakano Katsuo,
Shibamoto Shinji,
Kitajima Koji
Publication year - 1975
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.5570120305
Subject(s) - chemistry , solvolysis , hydrochloric acid , methanol , hydroxymethyl , catalysis , medicinal chemistry , organic chemistry , catalytic hydrogenation , hydrolysis
The reaction of 1‐phenyl‐1,2‐propanedione with 1,1‐disubstituted guanidines in methanol yielded 2‐(disubstituted amino)‐4‐hydroxy‐4‐methyl‐4 H ‐imidazoles (III). Compound III produced 5(4)methylimidazoles by catalytic hydrogenation and 5(4)chloromethylimidazoles (IV) by concentrated hydrochloric acid treatment. Solvolysis of IV in water and alcohols gave 5(4)hydroxymethyl‐ and 5(4)alkoxymethylimidazoles, respectively.