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Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles
- 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.
- Subjects :
- heterocycles
Letter
azoles
Organic Chemistry
Substitution (logic)
Triazole
Regioselectivity
Single step
Alkylation
Combinatorial chemistry
enones
Cycloaddition
lcsh:QD241-441
Chemistry
chemistry.chemical_compound
chemistry
Tosyl
Metal free
lcsh:Organic chemistry
1,2,3-triazoles
lcsh:Q
lcsh:Science
cycloaddition
Subjects
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