含窒素複素環化合物の研究(第43報)Pyridine誘導体を原料とし4級塩を経由するDicyclopropa[b, d](または[b, e])pyridine誘導体の2Step合成法

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1-Methylpyridinium iodide (1a), derived from pyridine (1a), was stirred in chloroform solution in the presence of sodium hydroxide and triethylbenzylammonium chloride, at room temperature, and a mixture of 1,1,3,3-tetrachloro-1a, 2,2a, 3a, 4,4a-hexahydro-2-methyl-4-trichloromethyl-1H, 3H-dicyclopropa [b, e] pyridine (12a) and 1,1,4,4-tetrachloro-1a, 2,3,3a, 4a, 4b-hexahydro-3-methyl-2-trichloromethyl-1H, 4H-dicyclopropa [b, d] pyridine (13a) formed. Similarly, corresponding dicyclopropa [b, e] pyridine derivative (12b) and dicyclopropa [b, d] pyridine derivative (13b) were obtained from 1-ethylpyridinium iodide (11b). In order to examine the substitution effect, the quaternary salts (11d-m) derived from 2-, 3-, or 4-methylpyridine, 2,3-, 2,4-, 2,6-, 3,4-, or 3,5-dimethylpyridine, and 2,4,6-trimethylpyridine were submitted to the same reaction and only one of either dicyclopropa [b, e] pyridine or dicyclopropa [b, d] pyridine derivative was formed according to the position of the methyl group substituted in the pyridine ring.
公益社団法人日本薬学会の論文
1979-11-25