From imidates to vinyl-1,2,4-triazoles: Synthesis, mechanistic aspects and first issues of their reactivity
2018
Azzouni, Safa | Abdelli, Abderrahmen | Gaucher, Anne | Arfaoui, Youssef | Efrit, Mohamed Lotfi | Prim, Damien
The reaction of variously substituted acylimidates with hydrazine derivatives represents an efficient and easy to set synthetic entry towards 5-vinyl-1,2,4-triazole derivatives. The construction of the triazole ring allows the installation of variety of substituent combination at the N(1), C(3) and C(5) positions of the five-membered heterocycle in good to high yields. The method reveals selective towards 5-vinyl-1,2,4-triazoles avoiding the potential formation of seven- and five-membered side-products as supported by theoretical calculations and NMR experiments. First lines of Pd-catalyzed arylation of the vinyl fragment towards 5-styryl-1,2,4-triazoles and Cu-catalyzed arylation at the N(1) site are finally described.
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