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Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides

A highly diastereoselective dearomative [3 + 2] 1,3-dipolar cycloaddition reaction of nitrobenzothiophenes with an in situ-generated nonstabilized azomethine ylides has been developed. The transformation provides a series of functionalized fused tricyclic benzo[4,5]thieno[2,3-c]pyrroles in good yiel...

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Autores principales: Wang, Kai-Kai, Xie, Yan-Xin, Li, Yan-Li, Chen, Rongxiang, Wang, Zhan-Yong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055820/
https://www.ncbi.nlm.nih.gov/pubmed/35520074
http://dx.doi.org/10.1039/d0ra05687a
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author Wang, Kai-Kai
Xie, Yan-Xin
Li, Yan-Li
Chen, Rongxiang
Wang, Zhan-Yong
author_facet Wang, Kai-Kai
Xie, Yan-Xin
Li, Yan-Li
Chen, Rongxiang
Wang, Zhan-Yong
author_sort Wang, Kai-Kai
collection PubMed
description A highly diastereoselective dearomative [3 + 2] 1,3-dipolar cycloaddition reaction of nitrobenzothiophenes with an in situ-generated nonstabilized azomethine ylides has been developed. The transformation provides a series of functionalized fused tricyclic benzo[4,5]thieno[2,3-c]pyrroles in good yields (up to 92%) under mild reaction conditions. In addition, a gram-scale experiment and the synthetic transformation of the cycloadduct further highlighted the synthetic utility. The relative configurations of the typical products were clearly confirmed by X-ray crystallography.
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spelling pubmed-90558202022-05-04 Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides Wang, Kai-Kai Xie, Yan-Xin Li, Yan-Li Chen, Rongxiang Wang, Zhan-Yong RSC Adv Chemistry A highly diastereoselective dearomative [3 + 2] 1,3-dipolar cycloaddition reaction of nitrobenzothiophenes with an in situ-generated nonstabilized azomethine ylides has been developed. The transformation provides a series of functionalized fused tricyclic benzo[4,5]thieno[2,3-c]pyrroles in good yields (up to 92%) under mild reaction conditions. In addition, a gram-scale experiment and the synthetic transformation of the cycloadduct further highlighted the synthetic utility. The relative configurations of the typical products were clearly confirmed by X-ray crystallography. The Royal Society of Chemistry 2020-08-04 /pmc/articles/PMC9055820/ /pubmed/35520074 http://dx.doi.org/10.1039/d0ra05687a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Wang, Kai-Kai
Xie, Yan-Xin
Li, Yan-Li
Chen, Rongxiang
Wang, Zhan-Yong
Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
title Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
title_full Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
title_fullStr Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
title_full_unstemmed Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
title_short Dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
title_sort dearomative [3 + 2] cycloaddition reaction of nitrobenzothiophenes with nonstabilized azomethine ylides
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9055820/
https://www.ncbi.nlm.nih.gov/pubmed/35520074
http://dx.doi.org/10.1039/d0ra05687a
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