Keteneおよびその誘導体の研究(第15報) : Quinoline-Diketene付加体とAmmoniaとの反応成績体

概要

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2-Methyl-12a, 13-dihydro-4H-pyrano[2,3-b]-2H-benzo[a]quinolizine-4,5-dione (I) was synthesized from quinoline and diketene and its treatment with ammonia water gave the pyridone compound (II) and the 4-amino compound (III). Treatment of II with phosphoryl chloride gave the 4-chloro compound (IV) which, when treated with sodium methoxide or hydrazine in dehyd. methanol, formed the 4-methoxy compound (VIII) or 4-hydrazino compound (VIII) respectively. Reduction of IV over Raney nickel gave the 4-chloro-11,12-dihydro compound (VI), while catalytic reduction over palladium-carbon gave the dechlorinated compound (V) of VI. III was derived to its acetate (VI) by its treatment with acetic anhydride. Reduction of III was also attempted. The NMR spectra of these products were examined.
公益社団法人日本薬学会の論文
1967-05-25