Abstract
It was shown that briefly boiling solutions of 2,5-diaryl-3,3,4,4-tetracyanopyrrolidines in DMF caused rearrangement into 5-aryl-2-(N-arylidenamino)-3,4-dicyanopyrroles, which are methylated with diazomethane both at the NH bond and at the carbon atom of the azomethine fragment.
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O. E. Nasakin, A. N. Lyschchinkov, P. M. Lukin, and A. Kh. Bulai, Khim. Geterotsikl. Soedin., No. 3, 353 (1994).
O. E. Nasakin, V. V. Alekseev, V. K. Promonenkov, Yu. P. Belov, A. Kh. Bulai, and S. Yu. Sil'vestrova, Khim. Geterotsikl. Soedin., No. 3, 402 (1981).
O. E. Nasakin, V. V. Alekseev, P. B. Terent'ev, A. Kh. Bulai, and M. Yu. Zabolotskaya, Khim. Geterotsikl. Soedin., No. 8, 1062 (1983).
J. March, Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. 3rd ed., Wiley-Interscience, New York (1985) [Russian translation, Vol. 4, Mir, Moscow (1988), p. 101].
A. B. Zolotoi, A. N. Lyshchikov, P. M. Lukin, A. I. Prokhorov, O. E. Nasakin, A. Kh. Bulai, and L. O. Atovmyan, Dokl. Akad. Nauk,313, 110 (1990).
J. B. Bastus, Tetrahedron Lett., No. 15. 955 (1963).
F. M. Dean and R. S. Johnson, J. Chem. Soc., Perkin Trans. I, No. 1, 224 (1981).
A. I. Prokhorov, A. B. Zolotoi, A. N. Lyshchikov, P. M. Lukin, O. E. Nasakin, and L. O. Atovmyan, Zh. Strukt. Khim.,32, 108 (1991).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 42–46, January, 1995.
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Nasakin, O.E., Lyshchikov, A.N., Lukin, P.M. et al. Thermal rearrangement of 2,5-diaryl-3,3,4,4-tetracyanopyrrolidines. Chem Heterocycl Compd 31, 35–39 (1995). https://doi.org/10.1007/BF01171287
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DOI: https://doi.org/10.1007/BF01171287