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Reactions of 2-(2-hetaryl)-2-(tetrahydrofuran-2-ylidene)acetonitriles with tertiary amines

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Chemistry of Heterocyclic Compounds Aims and scope

The reactions of 2-(2-hetaryl)-2-(tetrahydrofuran-2-ylidene)acetonitriles with conformationally rigid and heterocyclic tertiary amines were investigated. Compounds with bipolar structures were obtained: 1-cyano-1-(2-hetaryl)-5-(pyridinium-1-yl)-1-penten-2-olates and 5-(4-aza-1-azoniobicyclo[2.2.2]oct-1-yl)-1-cyano-1-(2-hetaryl)pent-1-en-2-olates.

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References

  1. A. W. Erian, Chеm. Rev., 93, 1991 (1993).

    Article  CAS  Google Scholar 

  2. M. Pätzel and J. Liebscher, Synthesis, 879 (1995).

  3. M. Pätzel and J. Liebscher, J. Heterocycl. Chem., 28, 1257 (1991).

    Article  Google Scholar 

  4. W. J. Middleton and V. A. Engelhardt, J. Am. Chem. Soc., 80, 2829 (1958).

    Article  CAS  Google Scholar 

  5. R. Neidlein, D. Kikelj, and W. Kramer, J. Heterocycl. Chem., 26, 1335 (1989).

    Article  CAS  Google Scholar 

  6. R. Neidlein and T. Eichinger, Helv. Chim. Acta, 75, 124 (1992).

    Article  CAS  Google Scholar 

  7. S. Rajappa and B. G. Advani, Indian J. Chem., 15B, 890 (1977).

    CAS  Google Scholar 

  8. R. Neidlein, G. Schröder, C. Krieger, and D. Kikelj, Helv. Chim. Acta, 75, 1039 (1992).

    Article  CAS  Google Scholar 

  9. R. Neidlein and S. Li, Synth. Commun., 25, 2379 (1995).

    Article  CAS  Google Scholar 

  10. R. Neidlein and S. Li, J. Heterocycl. Chem., 33, 1943 (1996).

    Article  CAS  Google Scholar 

  11. Yu. M. Volovenko, O. V. Khilya, and T. A. Volovnenko. Khim. Geterotsikl. Soedin., 439 (2003). [Chem. Heterocycl. Compd., 39, 394 (2003).]

  12. O. V. Khilya, T. A. Volovnenko, A. V. Turov, R. I. Zubatyuk, O. V. Shishkin, and Yu. V. Volovenko, Khim. Geterotsikl. Soedin., 1385 (2011). [Chem. Heterocycl. Compd., 47, 1141 (2011).]

  13. O. V. Khilya, Thesis for Cand. Chem. Sci. [in Ukrainian], Kiev (2003).

  14. Yu. M. Volovenko, O. V. Khilya, and T. A. Volovnenko, in: Oxygen- and Sulfur-Containing Heterocycles [in Russian], Vol. 1, IBS PRESS, Moscow (2003), p.217.

  15. O. V. Khilya, T. A. Volovnenko, A. V. Turov, R. I. Zubatyuk, O. V. Shishkin, and Yu. M. Volovenko, Khim. Geterotsikl. Soedin., 1891 (2012). [Chem. Heterocycl. Compd., 48, 1770 (2012).]

  16. M. R. Detty, J. Org. Chem., 44, 2073 (1979).

    Article  CAS  Google Scholar 

  17. E. Bellur and P. Langer, Tetrahedron, 62, 5426 (2006).

    Article  CAS  Google Scholar 

  18. O. V. Khilya, Ya. V. Baglai, and Yu. M. Volovenko, Khim. Geterotsikl. Soedin., 1157 (2010). [Chem. Heterocycl. Compd., 46, 934 (2010).]

  19. H.-B. Bürgi and J. D. Dunitz, Structure Сorrelation, Vol. 2, VCH, Weinheim (1994), p. 741.

  20. W. J. Middleton and V. A. Engelhardt, J. Am. Chem. Soc., 80, 2788 (1958).

    Article  CAS  Google Scholar 

  21. F. S. Babichev and Yu. M. Volovenko, Khim. Geterotsikl. Soedin., 1147 (1976). [Chem. Heterocycl. Compd., 12, 949 (1976).]

  22. Yu. M. Volovenko, T. V. Shokol, A. S. Merkulov, and F. S. Babichev, Ukr. Khim. Zh., 59, 55 (1993).

    CAS  Google Scholar 

  23. Yu. M. Volovenko, A. V. Tverdokhlebov, and T. A. Volovnenko, Khim. Geterotsikl. Soedin., 952 (2001). [Chem. Heterocycl. Compd., 37, 876 (2001).]

  24. Yu. M. Volovenko, T. A. Volovnenko, and A. V. Tverdokhlebov, Khim. Geterotsikl. Soedin., 1101 (2001). [Chem. Heterocycl. Compd., 37, 1011 (2001).]

  25. Y. M. Volovenko and E. V. Resnyanskaya, Mendeleev Commun., 12, 119 (2002).

    Article  Google Scholar 

  26. Yu. M. Volovenko, O. V. Khilya, T. A. Volovnenko, and A. V. Turov, Dop. NAN Ukrainy, No. 4, 128 (2003).

  27. G. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

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Correspondence to D. S. Milokhov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1881-1890, December, 2012.

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Milokhov, D.S., Khilya, O.V., Turov, A.V. et al. Reactions of 2-(2-hetaryl)-2-(tetrahydrofuran-2-ylidene)acetonitriles with tertiary amines. Chem Heterocycl Comp 48, 1761–1769 (2013). https://doi.org/10.1007/s10593-013-1207-3

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