Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles

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 pyrr...

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Bibliographic Details
Main Authors: Takashi Go, Akane Morimatsu, Hiroaki Wasada, Genzoh Tanabe, Osamu Muraoka, Yoshiharu Sawada, Mitsuhiro Yoshimatsu
Format: Article
Language:English
Published: Beilstein-Institut 2018-10-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
hydroamination
Pummerer reaction
pyrrole
pyrroloazepine
1,7-sulfur shift
Online Access:https://doi.org/10.3762/bjoc.14.250
Description
Summary: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-c]azepines or N-pyrrol-3-ylmethyl-N-(4-hydroxy-3-sulfanylpropyl)-p-toluenesulfonamides (diols). Seleno-Pummerer reactions of 3-selanylmethylpyrroles also proceeded via in situ generation of selenoxides, followed by a treatment with TBAH.
ISSN:1860-5397

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