Abstract
A scheme for the unusually ready selective hydrolysis of three of the cyano groups in 1,1,2,2-tetracyanoethane to 2-cyanoethane-1,1,2-tricarboxamide by the action of pyruvic acid was proposed. Only one cyano group undergoes hydrolysis in the reaction with sodium pyruvate. In the course of this reaction, 2-amino-5-methyl-3, 4-dicyano-4,5-dihydrofuran-4,5-dicarboximide, the structure of which was determined by x-ray diffraction investigation of the monocrystal, is formed.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
O. E. Nasakin, P. M. Lukin, P. B. Terent'ev, A. Kh. Bulai, B. A. Khaskin, and V. Ya. Zakharov, Zh. Org. Khim.,21, 662 (1985).
O. E. Nasakin, V. V. Alekseev, V. K. Promonenkov, A. Kh. Bulai, and S. Yu. Sil'vestrova, Khim. Geterotskikl. Soedin., No. 6, 744 (1981).
O. E. Nasakin, V. V. Pavlov, A. N. Lyshchikov, P. M. Lukin, V. N. Khrustalev, and Yu. T. Struchkov, Mendeleev Commun., No. 6, 236 (1995).
O. E. Nasakin, V. P. Sheverdov, P. M. Lukin, V. A. Tafeenko, and A. Kh. Bulai, Zh. Org. Khim.,28, 1841 (1992).
A. S. 1168554 USSR. O. E. Nasakin, E. G. Nikolaev, L. S. Shevnitsyn, P. B. Terent'ev, A. Kh. Bulai, V. D. Sheludyakov, A. N. Polivanov, and S. D. Danilov, Byull. Izobret., No. 27, 90 (1985).
O. E. Nasakin, P. M. Lukin, V. P. Sheverdov, A. N. Lyshchikov, A. Kh. Bulai, P. B. Terent'ev, and A. B. Zolotoi, Khim. Geterotsikl. Soedin., No. 6, 821 (1990).
Additional information
I. N. Ul'yanov Chuvashsk State University, Cheboksary 428015. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1472–1476, November, 1997.
Rights and permissions
About this article
Cite this article
Nasakin, O.E., Pavlov, V.V., Lyshchikov, A.N. et al. Unusually ready hydrolysis of nitrile groups in 1,1,2,2-tetracyanoethane by pyruvic acid. Chem Heterocycl Compd 33, 1272–1275 (1997). https://doi.org/10.1007/BF02320326
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02320326