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Chemospecific reactions of as-triazine ring reduction in sulfonyl derivatives of pyrazolo[5,1-c][1,2,4]triazines

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Chemistry of Heterocyclic Compounds Aims and scope

This study describes the reduction of 4-methyl- and 4-phenyl-3-(methylsulfonyl)pyrazolo[5,1-c][1,2,4]triazines and 3-[(4-methylphenyl)sulfonyl]pyrazolo[5,1-c][1,2,4]triazines, which were obtained by reactions of pyrazole-3(5)-diazonium salts with the appropriate β-ketosulfones. The interaction of sulfonyl derivatives of pyrazolo[5,1-c][1,2,4]triazines with sodium dithionite or thiourea 1,1-dioxide under mild conditions resulted in chemospecific partial reduction of the as-triazine ring. The configuration of the obtained pyrazolo[5,1-c][1,2,4]triazine dihydro derivatives was established by X-ray structural analysis.

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This study was supported by a grant from the Russian Science Foundation (project No. 15-13-10007).

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Authors and Affiliations

  1. Saratov State University named after N. G. Chernyshevsky, 83 Astrakhanskaya St, Saratov, 410012, Russia

    Irina V. Ledenyova & Alevtina Yu. Egorova

  2. Voronezh State University, 1 Universitetskaya Sq, Voronezh, 394006, Russia

    Irina V. Ledenyova, Pavel A. Kartavtsev & Khidmet S. Shikhaliev

Authors
  1. Irina V. Ledenyova
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  2. Pavel A. Kartavtsev
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  3. Khidmet S. Shikhaliev
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  4. Alevtina Yu. Egorova
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Correspondence to Irina V. Ledenyova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1128–1133

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Ledenyova, I.V., Kartavtsev, P.A., Shikhaliev, K.S. et al. Chemospecific reactions of as-triazine ring reduction in sulfonyl derivatives of pyrazolo[5,1-c][1,2,4]triazines. Chem Heterocycl Comp 53, 1128–1133 (2017). https://doi.org/10.1007/s10593-017-2183-9

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