An efficient one-pot strategy for the highly regioselective metal-free synthesis of 1,4-disubstituted-1,2,3-triazoles (original) (raw)
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Synlett, 2011
A metal-free, vinyl sulfone-based synthesis of 1,5-disubstituted-1,2,3-triazoles is reported for the first time. These triazoles are easily formed in a regioselective fashion by heating under reflux a mixture of a substituted vinyl sulfone and an organic azide 'on water'. This powerful and practical route has the potential to be exploited for the synthesis of complex 1,5-disubstituted-1,2,3triazoles.
Chem. Commun, 2015
Metal-free 1,3-dipolar cycloaddition reactions have proven to be a powerful tool for the assembly of key heterocycles, in particular diversely functionalized 1,2,3-triazoles. A number of metal-free (3+2)-cycloaddition approaches have been developed up to date with the aim to circumvent the use of metal catalysts allowing these reactions to take place in biological systems without perturbation of the naturally occurring processes. This feature article specifically provides an overview of emerging metal-free synthetic routes, and their mechanistic features, in the formation of functionalized 1,2,3-triazoles.
1,2,3-Triazoles from carbonyl azides and alkynes: filling the gap
Chemical Communications, 2014
Electron deficient azides are challenging substrates in CuAAC reactions. Particularly, when N-carbonyl azides are applied the formation of N-carbonyl triazoles has not yet been observed. We report herein the first example of this class of reaction, with a copper-based system that efficiently enables the synthesis of N-carbamoyl 1,2,3-triazoles by [3+2] cycloaddition of N-carbamoyl azides and alkynes.
Microwave assisted metal-free approach to access 1,2,3-triazoles through multicomponent synthesis
Current Research in Green and Sustainable Chemistry, 2020
The work illustrates multicomponent reaction of aldehydes, nitroalkanes and sodium azide for the metal-free synthesis of N-unsubstituted-1,2,3-triazoles using anthranilic acid as an organocatalyst under microwave irradiation. This is the first ever green protocol to synthesize 4-aryl-NH-1,2,3-triazoles from aromatic aldehyde, nitroalkane and sodium azide under microwave condition and offers broad substrate scope with good to excellent yields. Furthermore, using this efficient protocol gram scale synthesis of biologically important molecules were successfully carried out.
Journal of the Brazilian Chemical Society, 2013
As isatinas e os 1H-1,2,3-triazóis são duas classes de compostos com grande destaque na síntese orgânica e na química medicinal uma vez que são núcleos heterociclos com elevada reatividade, que permitem a obtenção de diversos compostos com importantes propriedades biológicas. Neste artigo, a síntese de novos 5`-(4-alquil/aril-1H-1,2,3-triazóis)-isatina via reação de cicloadição 1,3-dipolar catalisada por ácido acético é descrita. Isatin and 1H-1,2,3-triazoles are two classes of compounds with great prominence in organic synthesis and medicinal chemistry as they are heterocycle nuclei with a high reactivity allowing to obtain several compounds with important biological properties. Herein, the synthesis of novel 5'-(4-alquil/aril-1H-1,2,3-triazole)-isatin via reaction of 1,3-dipolar cycloaddition catalyzed by acetic acid is reported.