Quaternary salts of 2H-imidazoles
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2065-2069
- https://doi.org/10.1039/p19830002065
Abstract
Treatment of the 4,5-diphenyl-2H-imidazoles (1a–e) with alkyl iodides gives novel 1H+,2H-imidazolium salts (2) and (3). The metho-salt (2)N-methyl protons are readily exchanged for deuterium, and anions formed by the action of base give, with m-chlorobenzaldehyde, 2,3,5,7a-tetrahydroimidazo[5,1-b]-oxazoles (4), hydrolysable in acid to 2-(3-chlorophenyl)-2-hydroxyethylamine (6). Borohydride reduction of the metho-salt (2a) gave a dihydro-1H-imidazole (7) which with acid yielded 2-methylamino-1,2-diphenylethanone (8), and with methyl iodide a metho-salt (10). Direct (peracid) oxidation of 2H-imidazoles to N,N′-dioxides is reported for the first time.Keywords
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