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Nitropyrazoles 23. Synthesis of substituted N-amino-3-nitro-5-R-pyrazoles

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Abstract

The study is devoted to nucleophilic substitution of nitro groups in 1-amino-3,5-dinitropyrazole (1) and its amino group derived analogs. Compound 1 upon treatment with S-nucleophiles undergoes regioselective substitution of the nitro group at position 5. Azomethine 5 obtained by the condensation of 1 with benzaldehyde gives the nucleophilic substitution reaction with S-, O-and N-nucleophiles also with involvement of the nitro group at position 5. The synthesized 5-R-substituted azomethines 7–9 upon treatment with hydrazine hydrate form N-amino-5-R-3-nitropyrazoles and benzaldazine.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. V. Kormanov, T. K. Shkineva, I. A. Vatsadze, S. A. Shevelev & I. L. Dalinger

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  1. A. V. Kormanov
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  2. T. K. Shkineva
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  3. I. A. Vatsadze
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  4. S. A. Shevelev
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  5. I. L. Dalinger
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Correspondence to I. L. Dalinger.

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For Part 22, see Ref. 1.

On the occasion of the 80th anniversary of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0435–0442, February, 2014.

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Kormanov, A.V., Shkineva, T.K., Vatsadze, I.A. et al. Nitropyrazoles 23. Synthesis of substituted N-amino-3-nitro-5-R-pyrazoles. Russ Chem Bull 63, 435–442 (2014). https://doi.org/10.1007/s11172-014-0450-9

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