ストレプトニグリン関連化合物の合成研究(第5報) : ストレプトニグリン型構造を有する化合物の合成 : 複数環式化合物の合成研究第169報

概要

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Following previous work on the partial syntheses of AB and CD rings in I and II, and synthesis of ABCD skeleton possessing a substituent that can be derived to the C-ring, possibility of synthesizing I and II by the condensation of AB and CD rings was examined. The Ullmann reaction of 6-bromo-2,3-dimethyl-4-phenylpyridine (Vc) and 2-bromoquinoline (VIIa) afforded, through in a low yield, 2,3-dimethyl-4-phenyl-6-(2-quinolyl)pyridine (VIII), with a by-product formation of a dipyridyl derivative (IX). For the synthesis of the ABCD skeleton, XVIII, obtained in a good yield from 2-cyanoquinoline, was hydrolyzed with alkali and then with acid to 2-acetylquinoline and this was submitted to the Claisen-Schmidt reaction with piperonal and vanillin. The condensation products (XVIb〜c) were condensed with cyanoacetamide in the presence of piperidine and the pyridone derivatives (XVIIb〜c) with the ABCD skeleton were finally obtained.
社団法人日本薬学会の論文
1967-03-25