Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles
2-Aryl-1,2,3-triazoles were synthesized by cyclization of the corresponding glyoxal arylosazones, generated from commercial arylhydrazines. The deproto-metallation of 2-phenyl-1,2,3-triazole was attempted using different 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal (Zn, Cd, Cu, Co, Fe) co...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2012-07, Vol.10 (25), p.4878-4885 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Chevallier, Floris Blin, Thomas Nagaradja, Elisabeth Lassagne, Frédéric Roisnel, Thierry Halauko, Yury S Matulis, Vadim E Ivashkevich, Oleg A Mongin, Florence |
| description | 2-Aryl-1,2,3-triazoles were synthesized by cyclization of the corresponding glyoxal arylosazones, generated from commercial arylhydrazines. The deproto-metallation of 2-phenyl-1,2,3-triazole was attempted using different 2,2,6,6-tetramethylpiperidino-based mixed lithium-metal (Zn, Cd, Cu, Co, Fe) combinations, giving results in the case of Zn, Cd, and Cu. The lithium-zinc combination was next selected to apply the deprotonation-iodination sequence to all the 2-aryl-1,2,3-triazoles synthesized. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method. |
| doi_str_mv | 10.1039/c2ob25554e |
| format | Article |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acids - chemistry Chemical Sciences Metals - chemistry Models, Molecular Molecular Structure or physical chemistry Organic chemistry Theoretical and Triazoles - chemical synthesis |
| title | Deproto-metallation and computed CH acidity of 2-aryl-1,2,3-triazoles |
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