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
作者:Sadao Ohki、Fumiko Hamaguchi、Tokuko Yanagi、Motoyo Yoshino
DOI:10.1248/cpb.14.187
日期:——
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.
通过 1,1-二苯基-1,4-丁二醇 (VII)、2,2-二苯基四氢呋喃 (VI) 或 4-溴-1,1-二苯基-1-丁烯 (V) 与腈-氯化锡络合物的反应,一步合成了 2-取代的 3-二苯亚甲基-1-吡咯啉 (III)。2,5-二甲基(XI)和 2,5,5-三甲基-3-二苯基亚甲基-1-吡咯啉(XII)分别由 1,1-二苯基-1,4-戊二醇(IX)和 1,1-二苯基-4-甲基-1,4-戊二醇(X)制得。与通过里特反应制备 1-吡咯啉(II)相比,从 2-甲基-2,5-戊二醇(XIII)和 2,2-二甲基四氢呋喃(XV)通过相同反应制备 2-甲基-3-异亚丙基-1-吡咯啉(XIV)的事实令人感兴趣。用硼氢化钠还原 III 的碘甲烷,得到 1-甲基-2-烷基-3-二苯基亚甲基吡咯烷。发现 2-甲基化合物 (XVIc) 的碘甲烷具有较强的抗乙酰胆碱活性。