Reactions of 1,2,4,5-tetrazines with S-nucleophiles |
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Authors: | Tolshchina S. G. Ishmetova R. I. Ignatenko N. K. Korotina A. V. Ganebnykh I. N. Ol’shevskaya V. A. Kalinin V. N. Rusinov G. L. |
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Affiliation: | 1.I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620990, Ekaterinburg, Russian Federation ;2.A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation ; |
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Abstract: | The reactions of 3,6-disubstituted and azoloannulated 1,2,4,5-tetrazines containing heterocyclic leaving groups with S-nucleophiles were studied. The methods of introduction of functionalized thiols, including thiol derivatives of 1,7- and 1,2-dicarba-closo-dodecaboranes, into the tetrazine ring were developed. It was established for the first time that, instead of replacement of a leaving group in the tetrazine ring, the attack of S-nucleophile at the unsubstituted carbon atom occurs in the case of imidazo[1,2-b][1,2,4,5]tetrazines to form previously unknown products of nucleophilic substitution of the hydrogen atom. |
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