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Et(3)N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties

A robust transition-metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et(3)N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrocha...

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Detalles Bibliográficos
Autores principales: Singh, Dharmender, Kumar, Vipin, Singh, Virender
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7385337/
https://www.ncbi.nlm.nih.gov/pubmed/32765794
http://dx.doi.org/10.3762/bjoc.16.146
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author Singh, Dharmender
Kumar, Vipin
Singh, Virender
author_facet Singh, Dharmender
Kumar, Vipin
Singh, Virender
author_sort Singh, Dharmender
collection PubMed
description A robust transition-metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et(3)N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrochalcones followed by an incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed excellent light-emitting properties with quantum yields (Φ(F)) up to 47%.
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spelling pubmed-73853372020-08-05 Et(3)N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties Singh, Dharmender Kumar, Vipin Singh, Virender Beilstein J Org Chem Full Research Paper A robust transition-metal-free strategy is presented to access novel β-carboline-tethered benzothiophenone derivatives from 1(3)-formyl-β-carbolines using elemental sulfur activated by Et(3)N/DMSO. This expeditious catalyst-free reaction proceeds through the formation of β-carboline-based 2-nitrochalcones followed by an incorporation of sulfur to generate multifunctional β-carboline-linked benzothiophenones in good to excellent yields. The synthetic strategy could also be extended towards the synthesis of β-carboline-linked benzothiophenes. Moreover, the afforded products emerged as promising fluorophores and displayed excellent light-emitting properties with quantum yields (Φ(F)) up to 47%. Beilstein-Institut 2020-07-20 /pmc/articles/PMC7385337/ /pubmed/32765794 http://dx.doi.org/10.3762/bjoc.16.146 Text en Copyright © 2020, Singh 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
Singh, Dharmender
Kumar, Vipin
Singh, Virender
Et(3)N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
title Et(3)N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
title_full Et(3)N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
title_fullStr Et(3)N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
title_full_unstemmed Et(3)N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
title_short Et(3)N/DMSO-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
title_sort et(3)n/dmso-supported one-pot synthesis of highly fluorescent β-carboline-linked benzothiophenones via sulfur insertion and estimation of the photophysical properties
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7385337/
https://www.ncbi.nlm.nih.gov/pubmed/32765794
http://dx.doi.org/10.3762/bjoc.16.146
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