含窒素複素環化合物の研究(第47報)QuinolineからSpiro[cyclopropane-cyclopropa[c]quinoline]誘導体の生成について

概要

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Ouinaldine was dissolved in chloroform not containing any ethanol, 50% sodium hydroxide was added, and was stirred at room temperature in the presence of triethylbenzoylammonium chloride as a phase-transfer catalyst, by which 3'-formyl-1,1,1', 1'-tetrachloro-1a', 2', 3', 7b'-tetrahydrospiro (cyclopropane-2,2'-1H-cyclopropa [c] quinoline) (1a) was formed in a high yield. Treatment of 1a with lithium aluminum chloride in tetrahydrofuran gave a 3'-methyl compound (2a). Formation of 1a passes through the intermediate formation of 1,1-dichloro-1'-formyl-1', 2'-dihydrospiro [cyclopropane-2,2-quinoline] (3a). Presence of a small amount of polar solvent in the reaction mixture during formation of 1a results in the formation of 2-(2-chlorovinyl)-1,1-dichloro-1a, 7b-dihydro-1H-cyclopropa [c] quinoline (6a) as the major product. Reaction for the formation of compounds possessing a spiro ring, like 1a was found to be specific for quinoline derivatives having an active methylene in the 2-position and to have a fair general character. Spiro-ring compound was not formed from 1-methylisoquinoline.
公益社団法人日本薬学会の論文
1980-02-25