K. Turgunov, B. Tashkhodzhaev, T. F. Ibragimov
Jul 1, 2006
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Journal
Chemistry of Natural Compounds
Abstract
In an attempt to synthesize N-hydroxymethylcytisine from cytisine and formaldehyde solution (35%) in ether solution by the literature method [1], a compound with mp 131-132°C was produced. The PMR spectrum was consistent with N,N′-methylenebis-cytisine with mp 220-221°C. The reason for the melting point depression could have been solvate differences or polymorphism of the crystals because the conformational mobility of the bis-alkaloid favors the appearance of these phenomena. An x-ray crystal structure (XCS) of crystals of the product was carried out in order to elucidate the reason and to determine the molcular structure. The XCS results confirmed the structure N,N′-methylenebis-cytisine (1), in which the cytisine molecules are bound through a C14 methylene bridge. Crystals of 1 were the monohydrate, which may be the reason for the low melting point compared with the reported one [1]. Figure 1 shows the molecular structure of N,N′-methylenebiscytisine monohydrate.