Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides

An efficient cascade reaction involving sulfonylation and [2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides was described for the synthesis of 3-aryl-2,4-disulfonyl-1H-pyrroles. The main highlight of this study is the introduction of a new dual-functional rea...

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Autores principales: Salehi, Parvin, Tanbakouchian, Zahra, Farajinia-Lehi, Noushin, Shiri, Morteza
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8697567/
https://www.ncbi.nlm.nih.gov/pubmed/35423874
http://dx.doi.org/10.1039/d0ra10451e
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author Salehi, Parvin
Tanbakouchian, Zahra
Farajinia-Lehi, Noushin
Shiri, Morteza
author_facet Salehi, Parvin
Tanbakouchian, Zahra
Farajinia-Lehi, Noushin
Shiri, Morteza
author_sort Salehi, Parvin
collection PubMed
description An efficient cascade reaction involving sulfonylation and [2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides was described for the synthesis of 3-aryl-2,4-disulfonyl-1H-pyrroles. The main highlight of this study is the introduction of a new dual-functional reactivity of arylsulfonyl methyl isocyanides as the sulfonyl source as well as a 1,3-dipolar reagent in the same reaction. This system is facilitated by Cs(2)CO(3) mediation in DMSO and 100 °C conditions.
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spelling pubmed-86975672022-04-13 Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides Salehi, Parvin Tanbakouchian, Zahra Farajinia-Lehi, Noushin Shiri, Morteza RSC Adv Chemistry An efficient cascade reaction involving sulfonylation and [2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides was described for the synthesis of 3-aryl-2,4-disulfonyl-1H-pyrroles. The main highlight of this study is the introduction of a new dual-functional reactivity of arylsulfonyl methyl isocyanides as the sulfonyl source as well as a 1,3-dipolar reagent in the same reaction. This system is facilitated by Cs(2)CO(3) mediation in DMSO and 100 °C conditions. The Royal Society of Chemistry 2021-04-12 /pmc/articles/PMC8697567/ /pubmed/35423874 http://dx.doi.org/10.1039/d0ra10451e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/
spellingShingle Chemistry
Salehi, Parvin
Tanbakouchian, Zahra
Farajinia-Lehi, Noushin
Shiri, Morteza
Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides
title Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides
title_full Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides
title_fullStr Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides
title_full_unstemmed Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides
title_short Cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides
title_sort cascade synthesis of 2,4-disulfonylpyrroles by the sulfonylation/[2 + 3]-cycloaddition reactions of gem-dibromoalkenes with arylsulfonyl methyl isocyanides
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8697567/
https://www.ncbi.nlm.nih.gov/pubmed/35423874
http://dx.doi.org/10.1039/d0ra10451e
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