Go Takashi, Morimatsu Akane, Wasada Hiroaki, Tanabe Genzoh, Muraoka Osamu, Sawada Yoshiharu, Yoshimatsu Mitsuhiro
Department of Chemistry, Faculty of Education, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan.
Department of Chemistry, Faculty of Regional Study, Gifu University, Yanagido 1-1, Gifu 501-1193, Japan.
Beilstein J Org Chem. 2018 Oct 29;14:2722-2729. doi: 10.3762/bjoc.14.250. eCollection 2018.
A unique 1,7-S- and Se-shift reaction under Pummerer reaction conditions of 4-alkenyl-3-sulfinyl- and seleninylpyrroles was described. The usual Pummerer reaction of 4-(alkenylaminomethyl)-3-phenylsulfinylpyrroles and a successive reaction with tetrabutylammonium hydroxide (TBAH) yielded either pyrrolo[3,2-]azepines or -pyrrol-3-ylmethyl--(4-hydroxy-3-sulfanylpropyl)--toluenesulfonamides (diols). -Pummerer reactions of 3-selanylmethylpyrroles also proceeded via in situ generation of selenoxides, followed by a treatment with TBAH.
描述了在4-烯基-3-亚磺酰基和亚硒酰基吡咯的普默勒尔反应条件下独特的1,7-S-和Se-迁移反应。4-(烯基氨基甲基)-3-苯基亚磺酰基吡咯的常规普默勒尔反应以及随后与氢氧化四丁铵(TBAH)的反应产生了吡咯并[3,2-]氮杂卓或-吡咯-3-基甲基-(4-羟基-3-硫烷基丙基)-对甲苯磺酰胺(二醇)。3-硒甲基吡咯的普默勒尔反应也通过原位生成硒氧化物，然后用TBAH处理来进行。
