Abstract
Although the structure of kokusaginine has been determined by Anet et al., it was also confirmed by the following procedure. Catalytic reduction of kokusaginine with PtO2 in ethanolic solution produced colorless cubic crystals of the formula, C14H17O4N (IV), m.p. 182-183°, which by demethylation with conc. HCl, gave the compound, C13H15O4N (V), m.p. 263-264°. With acetic anhydride and pyridine it yielded a monoacetate, C15H17O5N, m.p. 235-236°, in colorless prisms. (IV) and (V) are assumed to be 3-ethyl-4, 6, 7.-trimethoxycarbostyril and 6, 7.-dimethoxy-3-ethyl-4-hydroxycarbostyril, respectively, as in the case of dictamnine, skimmianine, and kokusagine. On the other hand, the compound (V) was prepared synthetically as follows: Methyl 6-aminoveratrate and butyric anhydride gave methyl 6-(N-butyrylamino) veratrate (X), m.p. 107.5-108.5°, which, when treated with Na in toluene, afforded 6, 7.-dimethoxy-3-ethyl-4-hydroxycarbostyril, m.p. 263-264° (monoacetate, m.p. 235.5-236°). This substance is identical with (V) (as was also the acetate). The structure of kokusaginine, therefore, is 6, 7.-dimethoxydictamnine.
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