Synthesis of heterocyclic compounds containing the 3,3-dicyanoacrylamide fragment

The review summarizes the data for the 2005–2020 period on the methods of synthesis of heterocycles containing the 3,3-dicyanoacrylamide fragment. A group of reactions based on the introduction of the ylidenemalononitrile fragment into an existing 2-oxo-containing azaheterocycle is considered. A number of processes have been described in which simultaneous formation of both the azaheterocycle and the 3,3-dicyanoacrylamide fragment takes place.

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References

  1. 1.

    Deng, G.; Wang, Q.; Yang, M.; Li, B.; Han, T.; Chang, B.; Li, X.; Zhang, X.; Li, Z. Mini-Rev. Org. Chem. 2019, 16, 208.

    CAS  Article  Google Scholar 

  2. 2.

    Li, M.; Li, Y.; Zhang, H.; Wang, S.; Ao, Y.; Cui, Z. J. Mater. Chem. C 2017, 5, 4111.

    CAS  Article  Google Scholar 

  3. 3.

    Cho, M. J.; Choi, D. H.; Sullivan, P. A.; Akelaitis, A. J. P.; Dalton, L. R. Prog. Polym. Sci. 2008, 33, 1013.

    CAS  Article  Google Scholar 

  4. 4.

    Sharipova, S. M.; Kalinin, A. A. Chem. Heterocycl. Compd. 2017, 53, 36. [Khim. Geterotsikl. Soedin. 2017, 53, 36.]

  5. 5.

    Redon, S.; Eucat, G.; Ipuy, M.; Jeanneau, E.; Gautier-Luneau, I.; Ibanez, A.; Andraud, C.; Bretonnière, Y. Dyes Pigm. 2018, 156, 116.

    CAS  Article  Google Scholar 

  6. 6.

    Belikov, M. Yu.; Ievlev, M. Yu.; Fedoseev, S. V.; Ershov, O. V. New J. Chem. 2019, 43, 8414.

    CAS  Article  Google Scholar 

  7. 7.

    Reig, M.; Puigdollers, J.; Velasco, D. Phys. Chem. Chem. Phys. 2018, 20, 1142.

    CAS  Article  Google Scholar 

  8. 8.

    Al Garni, S. E.; Darwish, A. A. A. Phys. Scr. 2020, 95, ID 045806. https://doi.org/10.1088/1402-4896/ab623e.

  9. 9.

    King, J. A., Jr.; Houser, C. L.; Corkill, R. E.; Yee, G. T. J. Magn. Magn. Mater. 2020, 497, 165953.

    CAS  Article  Google Scholar 

  10. 10.

    Podlesný, J.; Pytela, O.; Klikar, M.; Jelínková, V.; Kityk, I. V.; Ozga, K.; Jedryka, J.; Rudyshd, M.; Bureš, F. Org. Biomol. Chem. 2019, 17, 3623.

    Article  Google Scholar 

  11. 11.

    Castro, M. C. R.; Belsley, M.; Raposo, M. M. M. Dyes Pigm. 2016, 131, 333.

    CAS  Article  Google Scholar 

  12. 12.

    Zhao, D.; Hu, J.; Liu, Z.; Xiao, B.; Wang, X.; Zhou, E.; Zhang, Q. Dyes Pigm. 2018, 151, 102.

    CAS  Article  Google Scholar 

  13. 13.

    Zhao, D.; Hu, J.; Cao, K.; Xiao, B.; Zhou, E.; Zhang, Q. Dyes Pigm. 2019, 162, 898.

    CAS  Article  Google Scholar 

  14. 14.

    Dhondge, A. P.; Chen, J.-Y.; Lin, T.; Yen, F.-M.; Li, K.-W.; Hsieh, H.-C.; Kuo, M.-Y. Org. Lett. 2018, 20, 40.

    CAS  Article  Google Scholar 

  15. 15.

    Dhondge, A. P.; Tsai, P.-C.; Nien, C.-Y.; Xu, W.-Y.; Chen, P.-M.; Hsu, Y.-H.; Li, K.-W.; Yen, F.-M.; Tseng, S.-L.; Chang, Y.-C.; Chen, H. J. H.; Kuo, M.-Y. Org. Lett. 2018, 20, 2538.

    CAS  Article  Google Scholar 

  16. 16.

    Dhondge, A. P.; Huang, Y.-X.; Lin, T.; Hsu, Y.-H.; Tseng, S.-L.; Chang, Y.-C.; Chen, H. J. H.; Kuo, M.-Y. J. Org. Chem. 2019, 84, 14061.

    CAS  Article  Google Scholar 

  17. 17.

    Chen, R.; Zhang, G.; Zhou, W. CN Patent 110790776, 2020.

  18. 18.

    Tafeenko, V. A.; Gurskiy, S. I. Cryst. Growth Des. 2016, 16, 940.

    CAS  Article  Google Scholar 

  19. 19.

    El-Sharief, A. M. Sh.; Ammar, Y. A.; Belal, A.; El-Sharief, M. A. M. Sh.; Mohamed, Y. A.; Mehany, A. B. M.; Elhag Ali, G. A. M.; Ragab, A. Bioorg. Chem. 2019, 85, 399.

    CAS  Article  Google Scholar 

  20. 20.

    Salem, M. A.; Ragab, A.; Askar, A. A.; El-Khalafawy, A.; Makhlouf, A. H. Eur. J. Med. Chem. 2020, 188, 111977.

  21. 21.

    El-Gaby, M. S. A.; El-Hag Ali, G. A. M.; El-Maghraby, A. A.; Abd El-Rahman, M. T.; Helal, M. H. M. Eur. J. Med. Chem. 2009, 44, 4148.

    CAS  Article  Google Scholar 

  22. 22.

    Chu, W.; Rothfuss, J.; d’Avignon, A.; Zeng, C.; Zhou, D.; Hotchkiss, R. S.; Mach, R. H. J. Med. Chem. 2007, 50, 3751.

    CAS  Article  Google Scholar 

  23. 23.

    Chu, W.; Rothfuss, J.; Zhou, D.; Mach, R. H. Bioorg. Med. Chem. Lett. 2011, 21, 2192.

    CAS  Article  Google Scholar 

  24. 24.

    Gupta, N.; Roy, T.; Ghosh, D.; Abdi, S. H. R.; Kureshy, R. I.; Khan, N. H.; Bajaj, H. C. RSC Adv. 2015, 5, 17843.

    CAS  Article  Google Scholar 

  25. 25.

    Zaghari, Z.; Azizian, J. Comb. Chem. High Throughput Screening 2018, 21, 609.

    CAS  Article  Google Scholar 

  26. 26.

    Demchuk, D. V.; Elinson, M. N.; Nikishin, G. I. Mendeleev Commun. 2011, 21, 224.

    CAS  Article  Google Scholar 

  27. 27.

    Tan, Z.-Y.; Wu, K.-X.; Huang, L.-S.; Wu, R.-S.; Du, Z.-Y.; Xu, D.-Z. Green Chem. 2020, 22, 332.

    CAS  Article  Google Scholar 

  28. 28.

    Huang, L.-S.; Lai, Y.-H.; Yang, C.; Xu, D.-Z. Appl. Organomet. Chem. 2019, 33, E4910.

  29. 29.

    Androsov, D. A.; Kishbaugh, T. L. S.; Gribble, G. W. Tetrahedron Lett. 2008, 49, 6621.

    CAS  Article  Google Scholar 

  30. 30.

    Ghozlan, S. A. S.; Ramadan, M. A.; Abdelmoniem, A. M.; Elwahy, A. H. M.; Abdelhamid, I. A. Turk. J. Chem. 2017, 41, 410.

    CAS  Article  Google Scholar 

  31. 31.

    Wu, S.-X.; Gu, B.-Q.; Xu, H.; Zheng, X.; Luo, X.; Deng, W.-P. Adv. Synth. Catal. 2019, 361, 4302.

    CAS  Article  Google Scholar 

  32. 32.

    Sabitov, A. A.; Dmitriev, M. V.; Belozerova, A. I.; Sal’nikova, T. V.; Maslivets, A. N. Russ. J. Org. Chem. 2020, 56, 1217. [Zh. Org. Khim. 2020, 56, 1109.]

  33. 33.

    Sal’nikova, T. V.; Dmitriev, M. V.; Bushmeleva, E. V.; Silaichev, P. S.; Maslivets, A. N. Russ. J. Org. Chem. 2018, 54, 564. [Zh. Org. Khim. 2018, 54, 564.]

  34. 34.

    Dmitriev, M. V.; Silaichev, P. S.; Maslivets, A. N. Russ. J. Org. Chem. 2015, 51, 74. [Zh. Org. Khim. 2015, 51, 77.]

  35. 35.

    Milovidova, A. G.; Belikov, M. Yu.; Ievlev, M. Yu.; Ershov, O. V.; Nasakin, O. E. Russ. J. Org. Chem. 2018, 54, 1790. [Zh. Org. Khim. 2018, 54, 1776.]

  36. 36.

    Youssef, M. M.; Amin, M. A. Molecules 2010, 15, 8827.

    CAS  Article  Google Scholar 

  37. 37.

    Faty, R. M.; Rashed, M. S.; Youssef, M. M. Molecules 2015, 20, 1842.

    Article  Google Scholar 

  38. 38.

    Aly, M. M. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 1497.

  39. 39.

    Burgess, J.; Steel, P. J. Tetrahedron Lett. 2006, 47, 4107.

    CAS  Article  Google Scholar 

  40. 40.

    Belikov, M. Yu.; Ievlev, M. Yu.; Milovidova, A. G.; Ershov, O. V. Russ. J. Org. Chem. 2017, 53, 1601. [Zh. Org. Khim. 2017, 53, 1565.]

  41. 41.

    Milovidova, A. G.; Belikov, M. Yu.; Ievlev, M. Yu.; Ershov, O. V.; Nasakin, O. E. Tafeenko, V. A. Tetrahedron Lett. 2020, 61, 151368.

    CAS  Article  Google Scholar 

  42. 42.

    Khil, A. M.; Kaminskii, V. A.; Slabko, O. Yu.; Kachanov, A. V.; Gerasimenko, A. V. J. Heterocycl. Chem. 2015, 52, 688.

    CAS  Article  Google Scholar 

  43. 43.

    Kayukova, O. V.; Kayukov, Ya. S.; Nikolaev, A. N.; Tafeenko, V. A.; Ershov, O. V.; Nasakin, O. E. Russ. J. Org. Chem. 2005, 41, 523. [Zh. Org. Khim. 2005, 41, 535.]

  44. 44.

    Kayukov, Ya. S.; Kayukova O. V.; Kalyagina, E. S.; Bardasov, I. N.; Ershov, O. V.; Nasakin, O. E.; Tafeenko, V. A. Russ. J. Org. Chem. 2011, 47, 392. [Zh. Org. Khim. 2011, 47, 400.]

  45. 45.

    Ershov, O. V.; Ievlev, M. Yu. Chem. Heterocycl. Compd. 2017, 53, 948. [Khim. Geterotsikl. Soedin. 2017, 53, 948.]

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This work was financially supported by the Russian Foundation for Basic Research (project No. 18-33-20268 mol_a_ved).

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Correspondence to Mikhail Yu. Belikov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(1), 1–6

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Belikov, M.Y., Milovidova, A.G. Synthesis of heterocyclic compounds containing the 3,3-dicyanoacrylamide fragment. Chem Heterocycl Comp 57, 1–6 (2021). https://doi.org/10.1007/s10593-021-02858-x

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Keywords

  • azaheterocycles
  • 3,3-dicyanoacrylamide fragment
  • ylidenemalononitrile fragment
  • polynitrile compounds