Abstract
2′-Oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole]-2,2,3,3-tetracarbonitriles reacted with oxygencentered nucleophiles to form addition products at the cyano groups with conservation of the three-membered ring. Reactions of the title compounds with alcohols required the presence of base catalyst, and the products, 2-amino-4,4-dialkoxy-2′-oxo-1′,2′-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1,5-dicarbonitriles, were converted into the corresponding 2-imino-2′,4-dioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1,5-dicarbonitriles and 2,2′,4-trioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1,5-dicarbonitriles by the action of acetic and sulfuric acids, respectively. The reactions with ketone oximes occurred in the absence of a catalyst, yielding 2-amino-4,4-bis(alkylideneaminooxy)-2′-oxo-1′,2′-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1,5-dicarbonitriles. The reactions with thiols, aliphatic amines, and anilines were accompanied by opening of the three-membered ring. In the reactions with triphenylphosphine and thiols 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)malononitrile was obtained, while morpholine and N,N-dimethylaniline gave rise, respectively, to 3,3-diaryl-and 3,3-dimorpholino-1H-indol-2(3H)-ones and tri- and dicyanoethylene derivatives.
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References
Lukin, P.M., Geksatsianotsiklopropan i ego analogi (Hexacyanocyclopropane and Its Analogs), Cheboksary: Poryadok, 2002, p. 101.
Kayukova, O.V., Kayukov, Ya.S., Lapteva, E.S., Bardasov, I.N., Ershov, O.V., and Nasakin, O.E., Russ. J. Org. Chem., 2006, vol. 42, p. 1414.
Yashkanova, O.V., Nasakin, O.E., Urman, Ya.G., Khrustalev, V.N., Nesterov, V.N., Antipin, M.Yu., Lukin, P.M., and Vershinin, E.V., Russ. J. Org. Chem., 1997, vol. 33, p. 484.
Yashkanova, O.V., Nasakin, O.E., Urman, Ya.G., Khrustalev, V.N., Nesterov, V.N., Antipin, M.Yu., and Lukin, P.M., Russ. J. Org. Chem., 1997, vol. 33, p. 475.
Lukin, P.M., Kayukova, O.V., Khrustalev, V.N., Nesterov, V.N., and Antipin, M.Yu., Russ. J. Org. Chem., 1999, vol. 35, p. 1693.
Walter, W., Chem. Ber., 1902, vol. 35, p. 1320.
Bergman, J. and Eklund, N., Tetrahedron, 1980, vol. 36, p. 1445.
Mckasick, B.C., Heckert, R.E., Cairns, T.L., Hoffman, D.D., and Mower, H.F., J. Am. Chem. Soc., 1958, vol. 80, p. 2806.
Schönberg, A. and Singer, E., Chem. Ber., 1965, vol. 983, p. 812.
Ruske, W. and Ruske, E., Chem. Ber., 1958, vol. 91, p. 2496.
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Original Russian Text © Ya.S. Kayukov, O.V. Kayukova, E.S. Kalyagina, I.N. Bardasov, O.V. Ershov, O.E. Nasakin, V.A. Tafeenko, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 3, pp. 400–408.
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Kayukov, Y.S., Kayukova, O.V., Kalyagina, E.S. et al. Reactions of 2′-oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole]-2,2,3,3-tetracarbonitriles with nucleophiles. Russ J Org Chem 47, 392–401 (2011). https://doi.org/10.1134/S1070428011030110
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DOI: https://doi.org/10.1134/S1070428011030110