クラリン関連化合物の合成研究 (第12報)
2-Ketocularimineの還元成績体について (複素環式化合物の合成研究 第113報)
1965 年 85 巻 8 号 p. 667-673
詳細
1965 年 85 巻 8 号 p. 667-673
The reduction product of 2-ketocularimine (III) with lithium aluminum hydride was submitted to alumina chromatography and cularimine (I), 2-hydroxycularimine (IX), and III were obtained. IX was acetylated with acetic anhydride and pyridine to a diacetyl compound (X), while Eschweiler-Clarke reaction of IX gave the N-methyl compound (XI) and dehydration of IX with phosphorus pentoxide afforded XV, whose reduction produced I. 2, 3, 6-Trimethoxydibenz [b, f] oxepin-10 (11H)-one was synthesized and its Pomeranz-Fritsch reaction with polyphosphoric acid gave 6, 9, 10-trimethoxy-12H benz [6, 7] oxepin-[2, 3, 4-i, j] isoquinoline (XX), whose oxidation with pyridine-chromic acid complex produced a ketone compound (XVII) identical with the product obtained by oxidation of cularimine with pyridine-chromic acid complex. Catalytic reduction of XX gave a product agreeing with authentic sample of cularimine.
