5-苯硫基吡哩酮及其异构体的合成研究

Synthesis of 5-phenylsulfenyl-2,3-dihydro-1-pyrrolizinone and its isomer

目的研究 1H 2 ,3 二氢 1 吡咯里嗪酮类衍生物的构效关系 ,设计合成了 5 苯硫基 2 ,3 二氢 1 吡咯里嗪酮 (1)。方法以吡咯为原料经Michael加成、苯硫化、分子内Hoesch反应合成目标化合物。结果在生成目标化合物的同时 ,生成了其同分异构体 7 苯硫基 2 ,3 二氢 1 吡咯里嗪酮(5 )。结论推测其生成机制为中间体 2 苯硫基 1 氰乙基吡咯在酸性下的异构化反应。

Aim In order to study the structure-activity relationship of 1 H -2,3-dihydro-1-pyrrolizinones,5-phenylsulfenyl-2,3-dihydro-1-pyrrolizinone(1)was designed.Methods The title compound was synthesized from pyrrole through the Michael addition,phenylsulfenation and cyclization.Results In the synthesis,while the title compound was synthesized,its isomer,7-phenylsulfenyl-2,3-dihydro-1-pyrrolizinone(5)was also obtained.Conclusion It is inferred that the rearrangement of the intermediate,3-(2-phenylsulfenyl-1-pyrrolyl)propionitrile resulted in the formation of compound 5.