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5-Substituted 3-Nitro-1-vinyl-1,2,4-triazoles

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Abstract

A series of 5-substituted 3-nitro-1-vinyl-1,2,4-triazoles were synthesized by alkaline treatment of the corresponding 1-(2-haloethyl- or 2-nitroxyethyl)-3-nitro-1,2,4-triazoles and by transvinylation of NH acids of the same series with vinyl acetate. The scope of applicability of the transvinylation procedure was established with respect to the azole pK a value. The vinylic double bond on the nitrogen was shown to be inactive toward both nucleophilic and electrophilic reagents, whereas the halogen atom in position 5 exhibits enhanced reactivity. The latter factor provides the possibility for versatile structural modification via nucleophilic replacement of the 5-halogen atom by various groups, including triazolate ion.

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  1. St. Petersburg State Institute of Technology, Moskovskii pr. 26, St. Petersburg, 198013, Russia

    T. P. Kofman & G. Yu. Kartseva

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  1. T. P. Kofman
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Kofman, T.P., Kartseva, G.Y. 5-Substituted 3-Nitro-1-vinyl-1,2,4-triazoles. Russian Journal of Organic Chemistry 37, 707–716 (2001). https://doi.org/10.1023/A:1012460103654

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