From imidates to vinyl-1,2,4-triazoles: Synthesis,mechanistic aspects and first issues of their reactivity |
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| Authors: | Safa Azzouni Abderrahmen Abdelli Anne Gaucher Youssef Arfaoui Mohamed Lotfi Efrit Damien Prim |
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| Affiliation: | 1. ILV, UVSQ, CNRS, University Paris-Saclay, 78035 Versailles France;2. Laboratory of Heterocyclic and Selective Organic Chemistry, Department of Chemistry, Faculty of Sciences of Tunis, University of Tunis El Manar, 2092 Tunis Tunisia;3. Laboratory of Physical Chemistry of Condensed Materials, Faculty of Sciences of Tunis, University of Tunis El Manar, 2092 Tunis Tunisia |
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| Abstract: | 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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| Keywords: | Acylimidates 1,2,4-triazoles DFT calculations Pd-catalyzed arylation |
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