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On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes

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Chemistry of Heterocyclic Compounds Aims and scope

It has been established that the interaction of cyanothioacetamide with 2-acetylcyclohexanone, 2-acetylcyclopentanone, or their enamines (2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes) contrary to the literature data have a non-regiospecific character and leads to the formation of mixtures of 3-cyano-4-methyl-5,6-tri(tetra)methylenepyridine-2(1 H)-thiones and 3-cyano-6-methyl-4,5-tri(tetra)methylene-pyridine-2(1 H)-thiones with a predominance of the latter.

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References

  1. L. A. Rodinovskaya, V. K. Promonenkov, Yu. A. Sharanin, V. P. Litvinov, and A. M. Shestopalov, in: Results in Science and Technology. Organic Chemistry Series [in Russian], Vol. 17, VINITI, Moscow (1989), p. 3.

  2. V. P. Litvinov, V. K. Promonenkov, Yu. A. Sharanin, and A. M. Shestopalov, Results in Science and Technology. Organic Chemistry Series [in Russian], Vol. 17, VINITI, Moscow (1989), p. 72.

  3. V. P. Litvinov, Usp. Khim., 68, 817 (1999).

    Google Scholar 

  4. Yu. A. Sharanin, A. M. Shestopalov, V. K. Promonenkov, and L. A. Rodinovskaya, Zh. Org. Khim., 20, 2432 (1984).

    CAS  Google Scholar 

  5. F. Al-Omran, A. Z. A. Elassar, and A. A. El-Khair, Tetrahedron, 57, 10163 (2001).

    Article  CAS  Google Scholar 

  6. Yu. A. Sharanin, A. M. Shestopalov, L. A. Rodinovskaya, V. K. Promonenkov, and V. P. Litvinov, Zh. Org. Khim., 20, 2442 (1984).

    CAS  Google Scholar 

  7. T. Suzuki, K. Sannohe, T. Ito, M. Maruyama, J. Kamiya, M. Hirayama, T. Kitano, and A. Awaya, US Pat. Appl. 4824952; Ref. Zh. Khim., 5 O69P (1990).

  8. K. Mito, S. Kajitani, T. Ito, T. Kitano, M. Maruyama, and M. Hirayama, Jap. Pat. Appl. 62004270; Ref. Zh. Khim., 8 O98 P (1988); Chem. Abs., 106, 156296 (1987).

    Google Scholar 

  9. F. Freeman, D. K. Farquhar, and R. I. Walker, J. Org. Chem., 33, 3648 (1968).

    Article  CAS  Google Scholar 

  10. F. Freeman and T. I. Ito, J. Org. Chem., 34, 3670 (1969).

    Article  CAS  Google Scholar 

  11. A. I. Ozols, Yu. E. Pelcher, Z. A. Kalme, Yu. Yu. Popelis, I. V. Turovskis, and G. Ya. Duburs, Khim. Geterotsikl. Soedin., 59 (1996). [Chem. Heterocycl. Compd., 32, 52 (1996).]

    Google Scholar 

  12. E. G. Paronikyan, S. N. Sirakanyan, S. V. Lindeman, M. S. Aleksanyan, A. A. Karapetyan, A. S. Noravyan, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 1137 (1989). [Chem. Heterocycl. Compd., 25, 953 (1989).]

    Google Scholar 

  13. E. G. Paronikyan, S. N. Sirakanyan, A. S. Noravyan, and D. A. Melkonyan, Arm. Khim. Zh., 44, 250 (1991).

    CAS  Google Scholar 

  14. V. D. Dyachenko and A. D. Dyachenko, Zh. Org. Khim., 44, 415 (2008).

    Google Scholar 

  15. V. D. Dyachenko, S. G. Krivokolysko, and V. P. Litvinov, Khim. Geterotsikl. Soedin., 81 (1998). [Chem. Heterocycl. Compd., 34, 73 (1998).]

    Google Scholar 

  16. G. Stork, A. Brizzolara, H. Landesman, J. Szmuszkovicz, and R. Terrell, J. Am. Chem. Soc., 85, 207 (1963).

    Article  CAS  Google Scholar 

  17. J. S. A. Brunskill, A. De, and D. F. Ewing, J. Chem. Soc., Perkin Trans. 1, 629 (1978).

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Authors and Affiliations

  1. “ChemEx” Laboratory, Vladimir Dal’ East-Ukrainian National University, 20-A/7 Molodyozhny kv., Lugansk, 91034, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

  2. Enamine Ltd, 67/45 Krasnotkatskaya St., Kiev, 02094, Ukraine

    V. V. Polovinko

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow, 117913, Russia

    V. P. Litvinov

Authors
  1. V. V. Dotsenko
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  2. S. G. Krivokolysko
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  3. V. V. Polovinko
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  4. V. P. Litvinov
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Correspondence to V. V. Dotsenko.

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V. P. Litvinov (Deceased)

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 328-338, February, 2012.

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Dotsenko, V.V., Krivokolysko, S.G., Polovinko, V.V. et al. On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes. Chem Heterocycl Comp 48, 309–319 (2012). https://doi.org/10.1007/s10593-012-0991-5

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  • DOI: https://doi.org/10.1007/s10593-012-0991-5

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