Abstract
5-(N-Isopropylthiocarbamoyl) derivatives of spinaceamine and spinacine have been synthesized for pharmacological testing. First, N-phenacylium salts of the given heterocycle are obtained via interaction of 1- and 1,2-substituted imidazo[4,5-c]pyridines with p -methoxyphenacyl bromide. The reduction of these salts with sodium boronhydride in alcohol leads to the formation of 5-(b-hydroxy-b- p -methoxyphenetyl) spinaceamines, and their boiling with reflux in concentrated hydrochloric acid leads to the terminal C-N 5 bond cleavage that yields 1-substituted and 1,2-disubstituted spinaceamines. The treatment of these compounds with isopropylisothiocyanate leads to the target 5-(N-isopropylthiocarbamoyl)spinaceamine derivatives. The reactions of lithium and potassium salts of spinacine with isopropylisothiocyanate yield thioureas, which have been converted into hydrochlorides by treating their ethanol solutions with hydrogen chloride.
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