Reaction of 2,2,3,3-tetracyanocyclopropyl ketones with water
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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.
KeywordsCyclopropane Cyano Group Dicarbonitrile Acetone Oxime Tricarbonitrile
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- 1.Bardasov, I.N., Kayukova, O.V., Kayukov, Ya.S., Ershov, O.V., and Nasakin, O.E., Zh. Prikl. Khim., 2009, vol. 82, p. 1332.Google Scholar
- 3.Bardasov, I.N., Kayukova, O.V., Kayukov, Ya.S., Ershov, O.V., Belikov, M.Yu., and Nasakin, O.E., Khim. Geterotsikl. Soedin., 2009, no. 9, p. 1297.Google Scholar
- 8.Sircar, S.S.G., J. Chem. Soc., 1927, p. 1257.Google Scholar
- 11.Brandenburg, K., DIAMOND, Bonn, Germany: Crystal Impact, 2000.Google Scholar