Eine alternative Synthese von Homohistamin und strukturverwandten (Imidazol-4-yl)alkylaminen/An Alternative Synthesis of Homohistamine and Structurally Related (Imidazole-4-yl)alkylamines

Abstract

Abstract 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 a-methyl-(1b) and 2-methylhomohistamine (1c) are synthesized. The resolution of 1b is achieved using (+)-and (-)-di-0-(4-toluoyl)tartaric acid. 1 are intermediates in the synthesis of impromidine like, H2 -histaminergic compounds.