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Synthesis of 1,2,4,5-tetrazines, symmetrically and unsymmetrically 3,6-disubstituted by N-nucleophiles

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Abstract

6-R-3-(3,5-Dimethylpyrazol-1-yl)-1,2,4,5-tetrazines with aliphatic, cycloaliphatic, and aromatic amines, and also with NH-heterocycles undergo a nucleophilic substitution of the dimethylpyrazole moiety yielding symmetrically and unsymmetrically substituted 1,2,4,5-tetrazines. In the 3,6-diimidazolyl-and 3,6-dibenzotriazolyl derivatives reactions of nucleophilic substitution of the heterocyclic moiety also occur. In some cases an ipsosubstitution of amino, hydrazino, and azido groups is observed.

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Authors and Affiliations

  1. Postovskii Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, Yekaterinburg, 620219, Russia

    G. L. Rusinov, N. I. Latosh, I. I. Ganebnykh, R. I. Ishmetova, N. K. Ignatenko & O. N. Chupakhin

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  1. G. L. Rusinov
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  2. N. I. Latosh
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  3. I. I. Ganebnykh
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  4. R. I. Ishmetova
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  5. N. K. Ignatenko
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  6. O. N. Chupakhin
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Original Russian Text © G.L. Rusinov, N.I. Latosh, I.I. Ganebnykh, R.I. Ishmetova, N.K. Ignatenko, O.N. Chupakhin, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 5, pp. 772–780.

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Rusinov, G.L., Latosh, N.I., Ganebnykh, I.I. et al. Synthesis of 1,2,4,5-tetrazines, symmetrically and unsymmetrically 3,6-disubstituted by N-nucleophiles. Russ J Org Chem 42, 757–765 (2006). https://doi.org/10.1134/S1070428006050198

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  • DOI: https://doi.org/10.1134/S1070428006050198

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