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Reaction of tetracyanocyclopropyl ketones with hydrazine hydrate

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Abstract

The reaction of 2,2,3,3-tetracyanocyclopropyl ketones with hydrazine involved the addition at the carbonyl and cyano groups and resulted in the formation of previously unknown polycyclic systems whose common feature was the presence in the structure of a pyridazine ring. In the general case 3-substituted 6-amino-8-oxo-4,5,7-tptriazatricyclo[4.3.0.02.9]-non-3-ene-1,9-dicarbonitriles were obtained. The reaction with 3-pivaloylcyclopropane-1,1,2,2-tetracarbonitrile took another route with the opening of the three-membered ring and the formation of 3-amino-7a-tert-butyl-6-oxo-5,6,7,7a-tetrahydro-4aH-pyrrolo[2,3-c]pyridazine-4,5-dicarbonitrile.

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, Cheboksary, 428015, Russia

    Ya. S. Kayukov, I. N. Bardasov, O. V. Kayukova, O. V. Ershov, O. E. Nasakin & A. V. Eremkin

  2. Lomonosov Moscow State University, Moscow, Russia

    V. A. Tafeenko

Authors
  1. Ya. S. Kayukov
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  2. I. N. Bardasov
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  3. O. V. Kayukova
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  4. O. V. Ershov
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  5. O. E. Nasakin
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  6. A. V. Eremkin
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  7. V. A. Tafeenko
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Corresponding author

Correspondence to Ya. S. Kayukov.

Additional information

Original Russian Text © Ya.S. Kayukov, I.N. Bardasov, O.V. Kayukova, O.V. Ershov, O.E. Nasakin, A.V. Eremkin, V.A. Tafeenko, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 5, pp. 717–722.

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Kayukov, Y.S., Bardasov, I.N., Kayukova, O.V. et al. Reaction of tetracyanocyclopropyl ketones with hydrazine hydrate. Russ J Org Chem 47, 722–727 (2011). https://doi.org/10.1134/S1070428011050113

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  • DOI: https://doi.org/10.1134/S1070428011050113

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