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Unusual regioselective reaction of 2,6-dichloro-4-methylnicotinonitrile with malononitrile dimer

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Abstract

The reaction of 2,6-dichloro-4-methylnicotinonitrile with malononitrile dimer in the presence of triethylamine leads to regioselective nucleophilic substitution of the chlorine atom at position 6 with the formation of triethylammonium 2-amino-3-(6-chloro-5-cyano-4-methyl-pyridin-2-yl)-1,1,3-tricyanoprop-2-en-1-ide. The structure of the product was confirmed by spectral methods and X-ray diffraction analysis.

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References

  1. V. K. Promonenkov, K. I. Kobrakov, M.-G. A. Shvehgeimer, V. A. Rudenko, M. V. Shimanskaya, L. Ya. Leitis, Sredstva zashchity rasteniy na osnove galogenpiridinov [Plant Protection Agents Based on Halopyridines], in Itogi nauki i tekhniki. Ser. Organicheskaya khimiya [Results of Science and Technology. Ser. Organic Chemistry], Volume 16, ed. M. I. Kabachnik, Moscow, VINITI, 1990, p. 314 (in Russian).

    Google Scholar 

  2. V. D. Strelkov, L. V. Dyadyuchenko, I. G. Dmitrieva, Sintez novykh gerbitsidnykh antidotov dlya podsolnechnika [Synthesis of New Herbicide Antidotes for Sunflower], Krasnodar, Prosveshchenie-Yug, 2014, p. 53 (in Russian).

    Google Scholar 

  3. V. V. Zakharychev, A. V. Kuzenkov, A. M. Martsynkevich, Chem. Heterocycl. Compd. (Engl. Transl.), 2020, 56, 1491.

    Article  CAS  Google Scholar 

  4. E. V. Babaev, Rev. J. Chem. (Engl. Transl.), 2011, 1, 161.

    Google Scholar 

  5. E. V. Babaev, Chem. Heterocycl. Compd. (Engl. Transl.), 2016, 52, 666.

    Article  CAS  Google Scholar 

  6. J. M. Blackburn, J. L. Roizen, Asian J. Org. Chem., 2019, 8, 920.

    Article  CAS  Google Scholar 

  7. K. Undheim, T. Benneche, Adv. Heterocycl. Chem., 1995, 62, 305.

    Article  CAS  Google Scholar 

  8. V. V. Dotsenko, D. S. Buryi, D. Yu. Lukina, S. G. Krivokolysko, Russ. Chem. Bull., 2020, 69, 1829.

    Article  CAS  Google Scholar 

  9. M. A. Bastrakov, A. K. Fedorenko, A. M. Starosotnikov, Russ. Chem. Bull., 2020, 69, 394.

    Article  CAS  Google Scholar 

  10. M. A. Bastrakov, A. M. Starosotnikov, I. V. Fedyanin, I. L. Dalinger, Chem. Heterocycl. Compd. (Engl. Transl.), 2021, 57, 95.

    Article  CAS  Google Scholar 

  11. Y. G. Shtyrlin, A. S. Petukhov, A. D. Strelnik, N. V. Shtyrlin, A. G. Iksanova, M. V. Pugachev, R. S. Pavelyev, M. S. Dzyurkevich, M. R. Garipov, K. V. Balakin, Russ. Chem. Bull., 2019, 68, 911.

    Article  CAS  Google Scholar 

  12. F. Vuillermet, J. Bourret, G. Pelletier, J. Org. Chem., 2021, 86, 388.

    Article  CAS  PubMed  Google Scholar 

  13. V. P. Litvinov, V. V. Dotsenko, S. G. Krivokolysko, Russ. Chem. Bull., 2005, 54, 864.

    Article  CAS  Google Scholar 

  14. E. A.-G. Bakhite, Phosphorus, Sulfur, Silicon, Relat. Elem., 2003, 178, 929.

    Article  CAS  Google Scholar 

  15. V. P. Litvinov, V. V. Dotsenko, S. G. Krivokolysko, Adv. Heterocycl. Chem., 2007, 93, 117.

    Article  CAS  Google Scholar 

  16. O. V. Ershov, M. A. Shishlikova, M. Yu. Ievlev, M. Yu. Belikov, V. N. Maksimova, Tetrahedron, 2019, 75, 130465.

    Article  CAS  Google Scholar 

  17. M. A. Gouda, J. Heterocycl. Chem., 2011, 48, 1.

    Article  CAS  Google Scholar 

  18. C. R. Hardy, Adv. Heterocycl. Chem., 1984, 36, 343.

    Article  CAS  Google Scholar 

  19. V. P. Litvinov, Russ. Chem. Rev., 2004, 73, 637.

    Article  CAS  Google Scholar 

  20. E. V. Babaev, V. L. Alifanov, A. V. Efimov, Russ. Chem. Bull., 2008, 57, 845.

    Article  CAS  Google Scholar 

  21. N. M. Tverdokhleb, G. E. Khoroshilov, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 56.

    Article  CAS  Google Scholar 

  22. D. A. Ponomarenko, G. E. Khoroshilov, D. A. Krasnikov, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 560.

    Article  CAS  Google Scholar 

  23. N. M. Tverdokhleb, G. E. Khoroshilov, V. V. Dotsenko, Tetrahedron Lett., 2014, 55, 6593.

    Article  CAS  Google Scholar 

  24. G. E. Khoroshilov, N. M. Tverdokhleb, V. S. Brovarets, E. V. Babaev, Tetrahedron, 2013, 69, 4353.

    Article  CAS  Google Scholar 

  25. N. M. Tverdokhleb, G. E. Khoroshilov, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 1141.

    Article  CAS  Google Scholar 

  26. N. M. Tverdokhleb, G. E. Khoroshilov, R. I. Zubatyuk, O. V. Shishkin, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 720.

    Article  CAS  Google Scholar 

  27. G. Khoroshilov, I. Demchak, T. Saraeva, Synthesis, 2008, 1541.

  28. G. E. Khoroshilov, T. A. Saraeva, K. Yu. Kuznetsov, Chem. Heterocycl. Compd. (Engl. Transl.), 2008, 44, 895.

    Article  CAS  Google Scholar 

  29. O. V. Ershov, I. N. Bardasov, Chem. Heterocycl. Compd. (Engl. Transl.), 2017, 53, 1178.

    Article  CAS  Google Scholar 

  30. V. V. Dotsenko, S. G. Krivokolysko, A. M. Semenova, Chem. Heterocycl. Compd. (Engl. Transl.), 2018, 54, 989.

    Article  CAS  Google Scholar 

  31. V. P. Litvinov, S. V. Roman, V. D. Dyachenko, Russ. Chem. Rev., 2000, 69, 201.

    Article  CAS  Google Scholar 

  32. V. P. Litvinov, Khimiya naftiridinov [Chemistry of Naphthyridines], Moscow, Ekonomika, 2008, p. 88 (in Russian).

    Google Scholar 

  33. Pat. PPR 145164; RZhKhim. [Chem. Ref. J.], 1989, 24 N 316 P (in Russian).

  34. Pat. PPR 139253; RZhKhim. [Chem. Ref. J.], 1988, 12 N 174 P (in Russian).

  35. W. A. Bolhofer, A. A. Deana, C. N. Habecker, J. M. Hoffman, N. P. Gould, A. M. Pietruszkiewicz, J. D. Prugh, M. L. Torchiana, E. J. Cragoe, Jr., R. Hirschmann, J. Med. Chem., 1983, 26, 538.

    Article  CAS  PubMed  Google Scholar 

  36. R. Skowroński, W. Strzyźewski, Pol. J. Chem., 1991, 65, 883.

    Google Scholar 

  37. Pat. PPR 139447; RZhKhim. [Chem. Ref. J.], 1988, 16 N 198 P (in Russian).

  38. I. G. Dmitrieva, L. V. Dyadyuchenko, E. A. Kaigorodova, Izv. vuzov. Khimiya i khim. tekhnol. [Izv. Higher Inst. Chemistry and Chem. Technol.], 2005, 48, No. 12, 29 (in Russian).

    CAS  Google Scholar 

  39. I. G. Dmitrieva, L. V. Dyadyuchenko, L. D. Konyushkin, E. A. Kaigorodova, Izv. vuzov. Khimiya i khim. tekhnol. [Izv. Higher Inst. Chemistry and Chem. Technol.], 2006, 49, No. 8, 119 (in Russian).

    CAS  Google Scholar 

  40. L. V. Dyadyuchenko, I. G. Dmitrieva, N. A. Aksenov, V. V. Dotsenko, Chem. Heterocycl. Compd. (Engl. Transl.), 2018, 54, 964.

    Article  CAS  Google Scholar 

  41. I. G. Dmitrieva, L. V. Dyadyuchenko, V. D. Strelkov, E. A. Kaigorodova, Chem. Heterocycl. Compd. (Engl. Transl.), 2009, 45, 1047.

    Article  CAS  Google Scholar 

  42. L. V. Dyadyuchenko, I. G. Dmitrieva, D. Yu. Nazarenko, V. D. Strelkov, Chem. Heterocycl. Compd. (Engl. Transl.), 2014, 50, 1259.

    Article  CAS  Google Scholar 

  43. V. V. Dotsenko, A. I. Ismiev, A. N. Khrustaleva, K. A. Frolov, S. G. Krivokolysko, E. A. Chigorina, A. P. Snizhko, V. M. Gromenko, I. S. Bushmarinov, R. K. Askerov, T. M. Pekhtereva, S. Yu. Suykov, E. S. Papayanina, A. V. Mazepa, A. M. Magerramov, Chem. Heterocycl. Compd. (Engl. Transl.), 2016, 52, 473.

    Article  CAS  Google Scholar 

  44. V. V. Dotsenko, S. G. Krivokolysko, A. N. Chernega, V. P. Litvinov, Russ. Chem. Bull., 2003, 52, 969.

    Article  CAS  Google Scholar 

  45. V. V. Dotsenko, E. A. Chigorina, S. G. Krivokolysko, Chem. Heterocycl. Compd. (Engl. Transl.), 2017, 53, 626.

    Article  CAS  Google Scholar 

  46. A. M. Semenova, R. V. Oganesyan, V. V. Dotsenko, E. A. Chigorina, N. A. Aksenov, I. V. Aksenova, E. E. Netreba, Russ. J. Gen. Chem., 2019, 89, 19.

    Article  CAS  Google Scholar 

  47. V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, A. N. Chernega, Chem. Heterocycl. Compd. (Engl. Transl.), 2007, 43, 599.

    Article  CAS  Google Scholar 

  48. V. V. Dotsenko, K. A. Frolov, E. A. Chigorina, A. N. Khrustaleva, E. Yu. Bibik, S. G. Krivokolysko, Russ. Chem. Bull., 2019, 68, 691.

    Article  CAS  Google Scholar 

  49. V. V. Dotsenko, A. N. Khrustaleva, K. A. Frolov, N. A. Aksenov, I. V. Aksenova, S. G. Krivokolysko, Russ. J. Gen. Chem., 2021, 91, 44.

    Article  CAS  Google Scholar 

  50. A. I. Ismiyev, V. V. Dotsenko, N. A. Aksenov, I. V. Aksenova, A. M. Magerramov, Russ. Chem. Bull., 2020, 69, 1938.

    Article  CAS  Google Scholar 

  51. V. V. Dotsenko, S. G. Krivokolysko, E. A. Chigorina, Russ. J. Gen. Chem., 2020, 90, 590.

    Article  CAS  Google Scholar 

  52. V. V. Dotsenko, V. A. Dushenko, N. A. Aksenov, I. V. Aksenova, E. E. Netreba, Russ. J. Gen. Chem., 2019, 89, 1752.

    Article  CAS  Google Scholar 

  53. E. A. Chigorina, A. V. Bespalov, V. V. Dotsenko, Russ. J. Gen. Chem., 2019, 89, 2018.

    Article  CAS  Google Scholar 

  54. V. V. Dotsenko, D. S. Buryi, D. Yu. Lukina, A. N. Stolyarova, N. A. Aksenov, I. V. Aksenova, V. D. Strelkov, L. V. Dyadyuchenko, Monatsh. Chem., 2019, 150, 1973.

    Article  CAS  Google Scholar 

  55. A. I. Ismiev, V. V. Dotsenko, N. A. Aksenov, G. Z. Mamedova, A. M. Magerramov, Russ. J. Gen. Chem., 2018, 88, 1533.

    Article  CAS  Google Scholar 

  56. L. V. Dyadyuchenko, V. D. Strelkov, S. N. Mikhailichenko, V. N. Zaplishny, Chem. Heterocycl. Compd. (Engl. Transl.), 2004, 40, 308.

    Article  CAS  Google Scholar 

  57. M. Mittelbach, Monatsh. Chem., 1985, 116, 689.

    Article  CAS  Google Scholar 

  58. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Federal Scientific Center for Biological Plant Protection, 350039, Krasnodar, p/o 39, Russian Federation

    L. V. Dyadyuchenko & V. S. Muraviev

  2. Kuban State University, 149 ul. Stavropolskaya, 350040, Krasnodar, Russian Federation

    V. V. Dotsenko & V. S. Muraviev

  3. North Caucasus Federal University, 1a ul. Pushkina, 355009, Stavropol’, Russian Federation

    V. V. Dotsenko, N. A. Aksenov & I. V. Aksenova

  4. I. T. Trubilin Kuban State Agrarian University, 13 ul. Kalinina, 350044, Krasnodar, Russian Federation

    I. G. Dmitrieva

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  1. L. V. Dyadyuchenko
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  2. V. V. Dotsenko
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  3. V. S. Muraviev
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  4. I. G. Dmitrieva
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  5. N. A. Aksenov
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Correspondence to V. V. Dotsenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1363–1367, July, 2021.

The research was carried out in accordance with the Russian state assignment No. 075-00376-19-00 of the Ministry of Science and Higher Education of the Russian Federation within the framework of research and development project on the Theme No. 0686-2019-0013.

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Dyadyuchenko, L.V., Dotsenko, V.V., Muraviev, V.S. et al. Unusual regioselective reaction of 2,6-dichloro-4-methylnicotinonitrile with malononitrile dimer. Russ Chem Bull 70, 1363–1367 (2021). https://doi.org/10.1007/s11172-021-3224-1

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