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Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

Authors :
Eufrânio N. da Silva Júnior
Renata G. Almeida
Irishi N. N. Namboothiri
Soumyaranjan Pati
Source :
Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 762-770 (2021), Beilstein Journal of Organic Chemistry
Publication Year :
2020
Publisher :
Beilstein Institut, 2020.

Abstract

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.

Details

Database :
OpenAIRE
Journal :
Beilstein Journal of Organic Chemistry, Vol 17, Iss 1, Pp 762-770 (2021), Beilstein Journal of Organic Chemistry
Accession number :
edsair.doi.dedup.....84ea5286ba16f693a8a688606c5dd85e
Full Text :
https://doi.org/10.3762/bxiv.2020.134.v1