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Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles
Desulfonylative alkylation of N-tosyl-1,2,3-triazoles under metal-free conditions leading to β-triazolylenones is reported here. The present study encompasses the synthesis of triazoles with a new substitution pattern in a single step from cyclic 1,3-dicarbonyl compounds and N-tosyl triazole in mode...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8022205/ https://www.ncbi.nlm.nih.gov/pubmed/33828620 http://dx.doi.org/10.3762/bjoc.17.66 |
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author | Pati, Soumyaranjan Almeida, Renata G da Silva Júnior, Eufrânio N Namboothiri, Irishi N N |
author_facet | Pati, Soumyaranjan Almeida, Renata G da Silva Júnior, Eufrânio N Namboothiri, Irishi N N |
author_sort | Pati, Soumyaranjan |
collection | PubMed |
description | Desulfonylative alkylation of N-tosyl-1,2,3-triazoles under metal-free conditions leading to β-triazolylenones is reported here. The present study encompasses the synthesis of triazoles with a new substitution pattern in a single step from cyclic 1,3-dicarbonyl compounds and N-tosyl triazole in moderate to high yields. Our synthesis takes place with complete regioselectivity as confirmed by crystallographic analysis which is rationalized by a suitable mechanistic proposal. This method provides an efficient, versatile and straightforward strategy towards the synthesis of new functionalized 1,2,3-triazoles. |
format | Online Article Text |
id | pubmed-8022205 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-80222052021-04-06 Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles Pati, Soumyaranjan Almeida, Renata G da Silva Júnior, Eufrânio N Namboothiri, Irishi N N Beilstein J Org Chem Letter Desulfonylative alkylation of N-tosyl-1,2,3-triazoles under metal-free conditions leading to β-triazolylenones is reported here. The present study encompasses the synthesis of triazoles with a new substitution pattern in a single step from cyclic 1,3-dicarbonyl compounds and N-tosyl triazole in moderate to high yields. Our synthesis takes place with complete regioselectivity as confirmed by crystallographic analysis which is rationalized by a suitable mechanistic proposal. This method provides an efficient, versatile and straightforward strategy towards the synthesis of new functionalized 1,2,3-triazoles. Beilstein-Institut 2021-03-31 /pmc/articles/PMC8022205/ /pubmed/33828620 http://dx.doi.org/10.3762/bjoc.17.66 Text en Copyright © 2021, Pati et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/terms/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 author(s) and source are credited and that individual graphics may be subject to special legal provisions. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms/terms) |
spellingShingle | Letter Pati, Soumyaranjan Almeida, Renata G da Silva Júnior, Eufrânio N Namboothiri, Irishi N N Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles |
title | Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles |
title_full | Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles |
title_fullStr | Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles |
title_full_unstemmed | Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles |
title_short | Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles |
title_sort | synthesis of β-triazolylenones via metal-free desulfonylative alkylation of n-tosyl-1,2,3-triazoles |
topic | Letter |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8022205/ https://www.ncbi.nlm.nih.gov/pubmed/33828620 http://dx.doi.org/10.3762/bjoc.17.66 |
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