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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Autores principales: Go, Takashi, Morimatsu, Akane, Wasada, Hiroaki, Tanabe, Genzoh, Muraoka, Osamu, Sawada, Yoshiharu, Yoshimatsu, Mitsuhiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6244179/
https://www.ncbi.nlm.nih.gov/pubmed/30498522
http://dx.doi.org/10.3762/bjoc.14.250
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author Go, Takashi
Morimatsu, Akane
Wasada, Hiroaki
Tanabe, Genzoh
Muraoka, Osamu
Sawada, Yoshiharu
Yoshimatsu, Mitsuhiro
author_facet Go, Takashi
Morimatsu, Akane
Wasada, Hiroaki
Tanabe, Genzoh
Muraoka, Osamu
Sawada, Yoshiharu
Yoshimatsu, Mitsuhiro
author_sort Go, Takashi
collection PubMed
description 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.
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spelling pubmed-62441792018-11-29 Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles Go, Takashi Morimatsu, Akane Wasada, Hiroaki Tanabe, Genzoh Muraoka, Osamu Sawada, Yoshiharu Yoshimatsu, Mitsuhiro Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2018-10-29 /pmc/articles/PMC6244179/ /pubmed/30498522 http://dx.doi.org/10.3762/bjoc.14.250 Text en Copyright © 2018, Go et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Go, Takashi
Morimatsu, Akane
Wasada, Hiroaki
Tanabe, Genzoh
Muraoka, Osamu
Sawada, Yoshiharu
Yoshimatsu, Mitsuhiro
Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
title Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
title_full Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
title_fullStr Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
title_full_unstemmed Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
title_short Unprecedented nucleophile-promoted 1,7-S or Se shift reactions under Pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
title_sort unprecedented nucleophile-promoted 1,7-s or se shift reactions under pummerer reaction conditions of 4-alkenyl-3-sulfinylmethylpyrroles
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6244179/
https://www.ncbi.nlm.nih.gov/pubmed/30498522
http://dx.doi.org/10.3762/bjoc.14.250
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