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Nitropyrazoles 15. Synthesis and some transformations of 1-(2,4-dinitrophenyl)-4-methyl-3,5-dinitropyrazole

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Abstract

The method for preparation of 1-(2,4-dinitrophenyl)-4-methyl-3,5-dinitropyrazole has been developed. Due to the larger CH-acidity of 4-Me-group compared to 1,4-dimethyl-3,5-dinitropyrazole, 1-(2,4-dinitrophenyl)-4-methyl-3,5-dinitropyrazole is capable of reacting with substituted benzaldehydes to afford 4-[(E)-2-arylvinyl]-1-(2,4-dinitrophenyl)-3,5-dinitropyrazoles. Under the action of nucleophiles, dinitrophenyl group is detached from the former compounds leading to previously unknown N-unsubstituted 4-[(E)-2-arylvinyl]-3,5-dinitropyrazoles.

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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. A. Zaitsev, I. A. Vatsadze, I. L. Dalinger, V. V. Kachala & S. A. Shevelev

  2. N. A. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    Yu. V. Nelyubina

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  1. A. A. Zaitsev
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  2. I. A. Vatsadze
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  3. I. L. Dalinger
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  4. V. V. Kachala
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  5. Yu. V. Nelyubina
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  6. S. A. Shevelev
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Correspondence to S. A. Shevelev.

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For Part 14, see Ref. 1.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2045—2053, October, 2009.

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Zaitsev, A.A., Vatsadze, I.A., Dalinger, I.L. et al. Nitropyrazoles 15. Synthesis and some transformations of 1-(2,4-dinitrophenyl)-4-methyl-3,5-dinitropyrazole. Russ Chem Bull 58, 2109–2117 (2009). https://doi.org/10.1007/s11172-009-0288-8

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  • DOI: https://doi.org/10.1007/s11172-009-0288-8

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