A Novel Dehydrative Ring-Transformation of 1-Alkyl-3-aroylpyrrolidines into 1-Alkyl-2-aryl-3-methylpyrroles
作者:Shuntaro Mataka、Hirohisa Kitagawa、Takehito Tsukinoki、Masashi Tashiro、Kazufumi Takahashi、Kichinosuke Kamata
DOI:10.1246/bcsj.68.1969
日期:1995.7
role derivatives in good yields. The ring-transformation of 3,4-dibenzoyl-1-methyl-2-phenylpyrrolidine occurred in two directions, giving the corresponding 3-benzyl- and 3-methylpyrrole derivative. Also, bicyclic pyrroles, such as 1H,3H-pyrrolo[1,2-c]thiazole, 2,3-dihydro-1H-pyrrolizine, and 5,6,7,8-tetrahydroindolizine, were prepared by the ring-transformation of bicyclic aroylpyrrolidines obtained
当在醇类溶剂(如乙二醇或丁醇)中加热时,4-取代的 3-芳酰基-1-烷基吡咯烷很容易通过氨基酸、多聚甲醛和 3-取代的 1-芳基-2-丙烯的缩合而获得-1-one,以良好的产率得到4-取代的1-烷基-2-芳基-3-甲基吡咯衍生物。3,4-二苯甲酰基-1-甲基-2-苯基吡咯烷的环转化发生在两个方向,得到相应的3-苄基-和3-甲基吡咯衍生物。此外,双环吡咯,如 1H,3H-吡咯并[1,2-c]噻唑、2,3-二氢-1H-吡咯嗪和 5,6,7,8-四氢茚茚,是通过环转化制备的由相应的环状氨基酸得到的双环芳酰基吡咯烷。提出了环转换的机制。