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Three-component synthesis of 2-(4-amino-2,5-dihydro-1H-imidazol-5-ylidene)malononitriles

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Abstract

2-(4-Amino-2,5-dihydro-1H-imidazol-4-ylidene)malononitriles were synthesized by three-component reaction of tetracyanoethylene, carbonyl compound, and ammonium acetate. The synthesis can be performed in two steps with intermediate isolation of 2-aminoethene-1,1,2-tricarbonitrile, as well as using preliminarily prepard 2-aminoethene-1,1,2-tricarbonitrile and 1,3,5-trisubstituted 2,4-diazapentadienes.

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References

  1. Middleton, W.J., Heckert, R.E., Little, E.L., and Krespas, C.G., J. Am. Chem. Soc., 1958, vol. 80, p. 2783.

    Article  CAS  Google Scholar 

  2. Sheverdov, V.P., Ershov, O.V., Nasakin, O.E., Chernushkin, A.N., Tafeenko, V.A., and Firgang, S.I., Tetrahedron, 2001, vol. 57, p. 5815.

    Article  CAS  Google Scholar 

  3. Sheverdov, V.P., Ershov, O.V., Nasakin, O.E., Chernushkin, A.N., Tafeenko, V.A., and Bulkin, V.V., Russ. J. Org. Chem., 2001, vol. 37, p. 291.

    Article  CAS  Google Scholar 

  4. Sheverdov, V.P., Ershov, O.V., Nasakin, O.E., Chernushkin, A.N., Efimov, R.N., and Tafeenko, V.A., Russ. J. Gen. Chem., 2002, vol. 72, p. 820.

    Article  CAS  Google Scholar 

  5. Sheverdov, V.P., Ershov, O.V., Nasakin, O.E., Lyshchikov, A.N., Efimov, R.N., Bulkin, V.V., and Tafeenko, V.A., Russ. J. Gen. Chem., 2002, vol. 72, p. 984.

    Article  CAS  Google Scholar 

  6. Smit, V.A., Lazareva, M.I., and Keipl, R., Ross. Khim. Zh., 2001, vol. 45, no. 4, p. 3.

    CAS  Google Scholar 

  7. Eremkin, A.V., Ershov, O.V., Mol’kov, S.N., Sheverdov, V.P., Nasakin, O.E., Kayukov, Ya.S., and Tafeenko, V.A., Russ. J. Org. Chem., 2006, vol. 42, p. 193.

    Article  CAS  Google Scholar 

  8. Eremkin, A.V., Molkov, S.N., Ershov, O.V., Kayukov, Y.S., Nasakin, O.E., Tafeenko, V.A., and Nurieva, E.V., Mendeleev Commun., 2006, vol. 16, p. 115.

    Article  Google Scholar 

  9. Maksimova, V.N., Eremkin, A.V., and Ershov, O.V., Abstracts of Papers, Mezhdunarodnaya konferentsiya molodykh uchenykh po fundamental’nym naukam “LOMONOSOV-2006” (Int. Conf. of Young Scientists on Fundamental Sciences “LOMONOSOV-2006”), Moscow: Sektsiya Khim., 2006, vol. 2, p. 179.

    Google Scholar 

  10. Zefirov, N.S. and Makhon’kov, D.I., Usp. Khim., 1980, vol. 49, p. 637.

    CAS  Google Scholar 

  11. McKusick, B.B., Heckert, R.E., Cairns, T.L., Coffman, D.D., and Mower, H.F., J. Am. Chem. Soc., 1958, vol. 80, p. 2806.

    Article  CAS  Google Scholar 

  12. Middleton, W.J., Little, E.L., Coffman, D.D., and Engelhardt, V.A., J. Am. Chem. Soc., 1958, vol. 80, p. 2795.

    Article  CAS  Google Scholar 

  13. Allen, F.H., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G., and Taylor, R., J. Chem. Soc., Perkin Trans. 2, 1987, p. S1.

  14. Grimmett, M.R., Imidazole and Benzimidazole Synthesis, London: Academic, 1997.

    Google Scholar 

  15. Ohtsuka, Y., J. Org. Chem., 1976, vol. 41, p. 713.

    Article  CAS  Google Scholar 

  16. de Vries, L., J. Org. Chem., 1971, vol. 36, p. 3442.

    Article  Google Scholar 

  17. Begland, R.W., Hartter, D.R., Jones, F.N., Sam, D.J., Sheppard, W.A., Webster, O.W., and Weigert, F.J., J. Org. Chem., 1974, vol. 39, p. 2341.

    Article  CAS  Google Scholar 

  18. Fatiadi, A.J., Synthesis, 1978, p. 165.

  19. Fatiadi, A.J., Synthesis, 1978, p. 241.

  20. Sharanin, Yu.A., Promonenkov, V.K., and Litvinov, V.P., Itogi Nauki Tekhn., Ser. Org. Khim., 1991, vol. 20, no. 1.

  21. Sharanin, Yu.A., Promonenkov, V.K., and Litvinov, V.P., Itogi Nauki Tekhn., Ser. Org. Khim., 1991, vol. 20, no. 2.

  22. Tafeenko, V.A., Paseshnichenko, K.A., Ershov, O.V., Eremkin, A.V., and Aslanov, L.A., Acta Crystallogr., Sect. C, 2005, vol. 61, p. 0434.

    Article  Google Scholar 

  23. Sheldrick, G.M., SHELXL97, Göttingen, Germany: Univ. of Göttingen, 1997.

    Google Scholar 

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Correspondence to O. V. Ershov.

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Original Russian Text © O.V. Ershov, A.V. Eremkin, Ya.S. Kayukov, A.N. Lyshchikov, O.E. Nasakin, V.A. Tafeenko, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 4, pp. 575–581.

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Ershov, O.V., Eremkin, A.V., Kayukov, Y.S. et al. Three-component synthesis of 2-(4-amino-2,5-dihydro-1H-imidazol-5-ylidene)malononitriles. Russ J Org Chem 44, 570–576 (2008). https://doi.org/10.1134/S1070428008040179

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  • DOI: https://doi.org/10.1134/S1070428008040179

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