- An Alternative Synthesis of Homohistamine and Structurally Related (Imidazole-4-yl)alkylamines
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Bromination of N-(4-oxopentyl)phthalimide (3) leads to isomeric bromoketones 2a and 2e, which undergo cyclisation with formamidine in liquid ammonia to yield homohistamine (1a) and 5-methylhistamine (1e).Similarly racemic α-methyl- (1b) and 2-methylhomohistamine (1c) are synthesized.The resolution of 1b is achieved using (+)- and (-)-di-O-(4-toluoyl)tartaric acid. 1 are intermediates in the synthesis of impromidine like, H2-histaminergic compounds. - Key words: Bromination of Methylketones, Halomethylketones, Histamine H2-Agonists, Homohistamine, Chiral Aminoalkylimidazoles
- Elz, Sigurd,Schunack, Walter
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p. 238 - 242
(2007/10/02)
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- A Short Synthesis of 5-Methylhistamine
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Methoxybromination of 4,5-dihydro-2-methylfuran (4), followed by treatment of the resulting bromoketal 5 with hot formamide, gave 4-(2-hydroxyethyl)-5-methyl-1H-imidazole (3) in 25percent yield.This method provides easy access to the selective H2-agonist 4-methylhistamine (1) via the chloromethyl intermediate 2.
- Pfister, Juerg R.,Kurz, Walter,Harrison, Ian T.
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p. 831 - 832
(2007/10/02)
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- 2H-imidazole-2-thione derivatives
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Imidazole derivatives which are useful intermediates for the production of compounds having pharmacological activity at histamine H2 receptors. A specific compound of the present invention is 4-(4-aminobutyl)-1,3-dihydro-5-methyl-2H-imidazole-2
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