Cyclization towards Carbon-Carbon Double Bond. III. A New Synthesis of 1-Pyrroline Derivatives and a Synthesis of 1,2-Dialkyl-3-diphenyl-methlenepyrrolidine Alkyl Halide, an Anti-acetylcholine Substance

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概要

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• 2-Subsituted 3-diphenylmethylene-1-pyrrolines (III) were synthesized in one step by the reaction of 1,1-diphenyl-1,4-butanediol (VII), 2,2-diphenyltetrahydrofuran (VI), or 4-bromo-1,1-diphenyl-1-butene (V) with nitrile-stannic chloride complex. 2,5-Dimethyl (XI) and 2,5,5-trimethyl-3-diphenylmethylene-1-pyrroline (XII) were obtained respectively from 1,1-diphenyl-1,4-pentanediol (IX) and 1,1-diphenyl-4-methyl-1,4-pentanediol (X). The fact that 2-methyl-3-isopropylidene-1-pyrroline (XIV) was obtained from 2-methyl-2,5-pentanediol (XIII) and 2,2-dimethyltetrahydrofuran (XV) by the same reaction was of interest in contrast with preparation of 1-pyrrolines (II) by the Ritter reaction. Reduction of the methiodide of III with sodium borohydride gave 1-methyl-2-alkyl-3-diphenylmethylenepyrrolidine. The methiodide of the 2-methyl compound (XVIc) was found to have a comparatively strong anti-acetylcholine activity.

• 社団法人日本薬学会の論文
• 1966-02-25

著者

• 大木 貞雄

  Tokyo College of Pharmacy

• 浜口 文子

  東京薬科大学

• 浜口 文子

  Tokyo College of Pharmacy

• 吉野 元世

  Tokyo College of Pharmacy

• 柳 徳子

  Tokyo College of Pharmacy

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