Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Pati, Soumyaranjan, Almeida, Renata G, da Silva Júnior, Eufrânio N, Namboothiri, Irishi N N
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2021
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
_version_ 1783674892837715968
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
work_keys_str_mv AT patisoumyaranjan synthesisofbtriazolylenonesviametalfreedesulfonylativealkylationofntosyl123triazoles
AT almeidarenatag synthesisofbtriazolylenonesviametalfreedesulfonylativealkylationofntosyl123triazoles
AT dasilvajunioreufranion synthesisofbtriazolylenonesviametalfreedesulfonylativealkylationofntosyl123triazoles
AT namboothiriirishinn synthesisofbtriazolylenonesviametalfreedesulfonylativealkylationofntosyl123triazoles