Russian Journal of Organic Chemistry

, Volume 48, Issue 4, pp 485–490 | Cite as

Reaction of 2,2,3,3-tetracyanocyclopropyl ketones with water

  • Ya. S. Kayukov
  • I. N. Bardasov
  • O. V. Ershov
  • O. E. Nasakin
  • O. V. Kayukova
  • V. A. Tafeenko
Article

Abstract

3-Benzoylcyclopropane-1,1,2,2-tetracarbonitrile reacted with water to give 2-benzoyl-1,3-dicyanocyclopropane-1-carboxamide as a result of hydrolysis of the cyano group in the trans position with respect to the carbonyl group and subsequent decarboxylation. The reaction of 3-benzoyl-3-methylcyclopropane-1,1,2,2-tetracarbonitrile with water involved heterocyclization with participation of the carbonyl group and cis-cyano groups, leading to 8-methyl-3,6-dioxo-1-phenyl-2,7-diazatricyclo[3.2.1.04,8]octane-4,5-dicarbonitrile. Hydrolysis of 3-alkylcyclopropane-1,1,2,2-tetracarbonitrile followed both reaction paths to produce mixtures of products, including 7-alkyl-4-amino-7-hydroxy-1,9-dioxo-3,8-diazatricyclo[4.3.0.01,5]non-3-ene-5-carbonitriles. In all cases, the three-membered ring was retained.

Keywords

Cyclopropane Cyano Group Dicarbonitrile Acetone Oxime Tricarbonitrile 

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Copyright information

© Pleiades Publishing, Ltd. 2012

Authors and Affiliations

  • Ya. S. Kayukov
    • 1
  • I. N. Bardasov
    • 1
  • O. V. Ershov
    • 1
  • O. E. Nasakin
    • 1
  • O. V. Kayukova
    • 2
  • V. A. Tafeenko
    • 3
  1. 1.I.N. Ul’yanov Chuvash State UniversityCheboksaryRussia
  2. 2.Chuvash Agricultural AcademyCheboksaryRussia
  3. 3.Faculty of ChemistryMoscow State UniversityMoscowRussia

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