Skip to main content
SpringerLink
Log in

Synthesis, structure, and reactions of (4-aryl-3-cyano-6-oxopiperidin-2-ylidene)malononitriles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of aromatic aldehydes with Meldrum's acid and malononitrile dimer in the presence of triethylamine led to the formation of (4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridin-2-yl)malononitrile triethylammonium salts, which were converted upon acidification to (4-aryl-3-cyano-6-oxopiperidin-2-ylidene)malononitriles. The reaction of these compounds with thioglycolic acid anilide was observed to produce derivatives of 1,6-naphthyridine or thieno[2,3-h][1,6]naphthyridine, depending on the conditions. Structures of (3-cyano-6-oxo-4-phenylpiperidin-2-ylidene)malononitrile and its triethylammonium salt were studied by X-ray structural analysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1
Figure 2
Figure 3
Figure 4
Figure 5

Similar content being viewed by others

References

  1. Fuentes, L.; Bonilla, L. A.; Contreras, M. C.; Lorenzo, M. J. Synth. Commun. 1992, 22, 2053.

    Article  CAS  Google Scholar 

  2. Daboun, H. A.; Abdou, S. E.; Khader, M. M. Heterocycles 1982, 19, 1925.

    Article  CAS  Google Scholar 

  3. Daboun, H. A.; Abdou, S. E.; Khader, M. M. Arch. Pharm. 1983, 316, 564.

    Article  CAS  Google Scholar 

  4. Elnadgi, M. H.; Erian, A. W. W. Arch. Pharm. 1991, 324, 853.

    Article  Google Scholar 

  5. Abu-Shanab, F. A.; Hessen, A. M.; Mousa, S. A. S. J. Heterocycl. Chem. 2007, 44, 787.

    Article  CAS  Google Scholar 

  6. Victory, P.; Busquets, N.; Borrell, J. I.; Teixidó, J.; Serra, B.; Matallana, J. L.; Junek, H.; Sterk, H. Heterocycles 1995, 41, 1013.

    Article  CAS  Google Scholar 

  7. Dyachenko, I. V.; Rusanov, E. B.; Gutov, A. V.; Vovk, M. V. Russ. J. Gen. Chem. 2013, 83, 1383. [Zh. Obshch. Khim. 2013, 83, 1132.]

  8. Dyachenko, I. V.; Vovk, M. V. Chem. Heterocycl. Compd. 2012, 48, 1574. [Khim. Geterotsikl. Soedin. 2012, 1685.]

  9. Junek, H. Monatsh. Chem. 1965, 96, 2046.

    Article  CAS  Google Scholar 

  10. Koitz, G.; Thierrichter, B.; Junek, H. Heterocycles 1983, 20, 2405.

    Article  CAS  Google Scholar 

  11. Teixidó, J.; Borrell, J. I.; Serra, B.; Matallana, J. L.; Colominas, C.; Carrión, F.; Pascual, R.; Falcó, J. L.; Batllori, X. Heterocycles 1999, 50, 739.

    Article  Google Scholar 

  12. Victory, P. J.; Teixidó, J.; Borrell, J. I. Heterocycles 1992, 34, 1905.

    Article  CAS  Google Scholar 

  13. Carrión, F.; Mont, N.; Batllori, X.; Borrell, J. I.; Teixidó, J. Tetrahedron 2007, 63, 215.

    Article  Google Scholar 

  14. Carrión, F.; Pettersson, S. H.; Rifá, J.; Farran, J.; Batllori, X.; Borrell, J. I.; Teixidó, J. Mol. Diversity 2010, 14, 755.

    Article  Google Scholar 

  15. Moustafa, M. S.; Al-Mousawi, S. M.; Hilmy, N. M.; Ibrahim, Y. A.; Liermann, J. C.; Meier, H.; Elnagdi, M. H. Molecules 2013, 18, 276.

    Article  CAS  Google Scholar 

  16. Helmy, N. M.; El-Baih, F. E. M.; Al-Alshaikh, M. A.; Moustafa, M. S. Molecules 2011, 16, 298.

    Article  CAS  Google Scholar 

  17. Fadda, A. A.; Refat, H. M. Monatsh. Chem. 1999, 130, 1487.

    Article  CAS  Google Scholar 

  18. Fahmy, S. M.; Abd Allah, S. O.; Mohareb, R. M. Synthesis 1984, 976.

  19. Abdelrazek, F. M.; Michael, F. A.; Mohamed, A. E. Arch. Pharm. 2006, 339, 305.

  20. Fuentes, L.; Vaquero, J. J.; Soto, J. L. Synthesis 1982, 320.

  21. Hassanien, A. Z. A.; Ghozlan, S. A. S.; Elnagdi, M. H. J. Heterocycl. Chem. 2003, 40, 225.

    Article  CAS  Google Scholar 

  22. Elgemeie, G. E. H.; Hanfy, N.; Hopf, H.; Jones, P. G. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1998, C54, 820.

  23. Elgemeie, G. H.; Metwally, N. H. J. Chem. Res., Synop. 1999, 208.

  24. Abu-Shanab, F. A.; Redhouse, A. D.; Thompson, J. R.; Wakefield, B. J. Synthesis 1995, 557.

  25. Sharanin, Yu. A.; Krivokolysko, S. G.; Dyachenko, V. D. Russ. J. Org. Chem. 1994, 30, 620. [Zh. Org. Khim. 1994, 30, 581.]

  26. Sharanin, Yu. A.; Baskakov, Yu. A.; Abramenko, Yu. T.; Putsykin Yu. G.; Nazarova, E. B.; Vasilyev, A. F. J. Org. Chem. USSR 1984, 20, 1373. [Zh. Org. Khim. 1984, 20, 1508.]

  27. Sharanin, Yu. A.; Khoroshilov, G. E.; Nefedov, O. M.; Litvinov, V. P.; Shestopalov, A. M. J. Org. Chem. USSR 1989, 25, 1182. [Zh. Org. Khim. 1989, 25, 1315.]

  28. Shestopalov, A. M.; Rodinovskaya, L. A.; Litvinov, V. P.; Sharanin, Yu. A. Dokl. Chem. 1990, 314, 271. [Dokl. Akad. Nauk SSSR, Ser. Khim. 1990, 314(4), 870.]

  29. Freeman, F. Chem. Rev. 1969, 69, 591.

    Article  CAS  Google Scholar 

  30. Fatiadi, A. J. Synthesis 1978, 165.

  31. Sharanin, Yu. A.; Promonenkov, V. K.; Litvinov, V. P. in Results of Science and Technology. Organic Chemistry, Shvekhgeimer, M.-G. A., Ed.; VINITI: Moscow, 1991, Vol. 20 (Part 2), p. 59.

  32. Dyachenko, V. D.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 1997, 46, 1912. [Izv. Akad. Nauk, Ser. Khim. 1997, 2016.]

  33. Dyachenko, V. D.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 1997, 46, 1758. [Izv. Akad. Nauk, Ser. Khim. 1997, 1852.]

  34. Nesterov, V. N.; Krivokolysko, S. G.; Dotsenko, V. V.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 1997, 46, 990. [Izv. Akad. Nauk, Ser. Khim. 1997, 1029.]

  35. Krivokolysko, S. G.; Chernega, A. N.; Litvinov, V. P. Chem. Heterocycl. Compd. 2002, 38, 1269. [Khim. Geterotsikl. Soedin. 2002, 1438.]

  36. Dotsenko, V. V.; Krivokolysko, S. G.; Chernega, A. N.; Litvinov, V. P. Dokl. Chem. 2003, 389(4–6), 92. [Dokl. Akad. Nauk 2003, 389(6), 763.]

  37. Dotsenko, V. V.; Krivokolysko, S. G.; Chernega, A. N.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2003, 52, 969. [Izv. Akad. Nauk, Ser. Khim. 2003, 918.]

  38. Frolov, K. A.; Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2005, 54, 1335. [Izv. Akad. Nauk, Ser. Khim. 2005, 1297.]

  39. Dotsenko, V. V.; Krivokolysko, S. G.; Litvinov, V. P. Russ. Chem. Bull., Int. Ed. 2012, 61, 131. [Izv. Akad. Nauk, Ser. Khim. 2012, 129.]

  40. Dotsenko, V. V.; Lebedeva, I. A.; Krivokolysko, S. G.; Povstyanoi, M. V.; Povstyanoi, V. M.; Kostyrko, E. O. Chem. Heterocycl. Compd. 2012, 48, 462. [Khim. Geterotsikl. Soedin. 2012, 492.]

  41. Frolov, K. A.; Dotsenko, V. V.; Krivokolysko, S. G. Chem. Heterocycl. Compd. 2012, 48, 1006. [Khim. Geterotsikl. Soedin. 2012, 1083.]

  42. Osolodkin, D. I.; Kozlovskaya, L. I.; Dueva, E. V.; Dotsenko, V. V.; Rogova, Y. V.; Frolov, K. A.; Krivokolysko, S. G.; Romanova, E. G.; Morozov, A. S.; Karganova, G. G.; Palyulin, V. A.; Pentkovski, V. M.; Zefirov, N. S. ACS Med. Chem. Lett. 2013, 4(9), 869.

    Article  CAS  Google Scholar 

  43. Dotsenko, V. V.; Frolov, K. A.; Pekhtereva, T. M.; Papaianina, O. S.; Suykov, S. Yu.; Krivokolysko, S. G. ACS Comb. Sci. 2014, 16, 543.

    Article  CAS  Google Scholar 

  44. Ivanov, A. S.; Tugusheva, N. Z.; Solov'eva, N. P.; Granik, V. G. Russ. Chem. Bull., Int. Ed. 2002, 51, 2121. [Izv. Akad. Nauk, Ser. Khim. 2002, 1966.]

  45. Ivanov, A. S.; Tugusheva, N. Z.; Alekseeva, L. M.; Granik, V. G. Russ. Chem. Bull., Int. Ed. 2003, 52, 1182. [Izv. Akad. Nauk, Ser. Khim. 2003, 1120.]

  46. Pinheiro, L. C. S.; Borges, J. C.; Oliveira, C. D.; Ferreira, V. F.; Romeiro, G. A.; Marques, I. P.; Abreu, P. A.; Frugulheti, I. C. P. P.; Rodrigues, C. R.; Albuquerque, M. G.; Castro, H. C.; Bernardino, A. M. R. ARKIVOC 2008, (xiv), 77.

  47. Litvinov, V. P.; Dotsenko, V. V.; Krivokolysko, S. G. Chemistry of Thienopyridines and Related Systems; Belen'kii, L. I., Ed.; Nauka: Moscow, 2006.

    Google Scholar 

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

    Article  CAS  Google Scholar 

  49. Litvinov, V. P.; Dotsenko, V. V.; Krivokolysko, S. G. Russ. Chem. Bull., Int. Ed. 2005, 54, 864. [Izv. Akad. Nauk, Ser. Khim. 2005, 847.]

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

  51. Brown, D. J. In The Chemistry of Heterocyclic Compounds, Taylor, E. C; Wipf, P., Eds.; John Wiley and Sons: Hoboken (USA), 2008, Vol. 63, pp. 69, 125.

  52. Litvinov, V. P. Adv. Heterocycl. Chem. 2006, 91, 189.

  53. Litvinov, V. P.; Roman, S. V.; Dyachenko, V. D. Russ. Chem. Rev. 2000, 69, 201. [Usp. Khim. 2000, 69, 218.]

  54. Paudler, W. W.; Kress, T. J. Adv. Heterocycl. Chem. 1970, 11, 123.

    Article  CAS  Google Scholar 

  55. Paudler, W.; Sheets, R. Adv. Heterocycl. Chem. 1983, 33, 147.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  57. Nesterova, I. N.; Shanazarov, A. K.; Poznyak, A. M.; Lakoza, M. I.; Shemeryankin, B. V.; Granik, V. G. Pharm. Chem. J. 1994, 28, 583. [Khim.-Farm. Zh. 1994, 28(8), 41.]

  58. Sheldrick, G. M. SHELXTL, v. 6.12, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2001.

Download references

Author information

Authors and Affiliations

  1. Kuban State University, 149 Stavropol’skaya St., Krasnodar, 350040, Russia

    Victor V. Dotsenko, Anastasiya N. Khrustaleva, Konstantin A. Frolov, Sergey G. Krivokolysko, Aleksey P. Snizhko & Vladimir M. Gromenko

  2. Baku State University, 23 Academic Zahid Khalilov St., AZ 1148, Baku, AZ-1073/1, Azerbaijan

    Arif I. Ismiev, Rizvan K. Askerov & Abel M. Magerramov

  3. Federal State Unitary Enterprise “ State Scientific Research Institute of Chemical Reagents and High Purity Chemical Substances” (FSUE “ IREA”), 3 Bogorodsky Val, Moscow, 107076, Russia

    Elena A. Chigorina

  4. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991 V-334, Russia

    Ivan S. Bushmarinov

  5. L. M. Litvinenko Institute of Physico-Organic Chemistry and Coal Chemistry, 70 R. Luxemburg St., Donetsk, 83114, Ukraine

    Tatyana M. Pekhtereva

  6. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02660, Ukraine

    Sergey Yu. Suykov

  7. University of Erlangen-Nuremberg, Institute of Organic Chemistry II, 42 Henkestr., Erlangen, 91054, Germany

    Elena S. Papayanina

  8. A. V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, 86 Lustdorfskaya Rd., Odessa, 65080, Ukraine

    Aleksandr V. Mazepa

Authors
  1. Victor V. Dotsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Arif I. Ismiev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Anastasiya N. Khrustaleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Konstantin A. Frolov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sergey G. Krivokolysko
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Elena A. Chigorina
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Aleksey P. Snizhko
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Vladimir M. Gromenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Ivan S. Bushmarinov
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. Rizvan K. Askerov
    View author publications

    You can also search for this author in PubMed Google Scholar

  11. Tatyana M. Pekhtereva
    View author publications

    You can also search for this author in PubMed Google Scholar

  12. Sergey Yu. Suykov
    View author publications

    You can also search for this author in PubMed Google Scholar

  13. Elena S. Papayanina
    View author publications

    You can also search for this author in PubMed Google Scholar

  14. Aleksandr V. Mazepa
    View author publications

    You can also search for this author in PubMed Google Scholar

  15. Abel M. Magerramov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Victor V. Dotsenko.

Additional information

The Supplementary Iiformation file containing spectra of compounds, as well as the X-ray crystallographic data for compounds 6a, 7a, is available at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(7), 473–483

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 10289 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dotsenko, V.V., Ismiev, A.I., Khrustaleva, A.N. et al. Synthesis, structure, and reactions of (4-aryl-3-cyano-6-oxopiperidin-2-ylidene)malononitriles. Chem Heterocycl Comp 52, 473–483 (2016). https://doi.org/10.1007/s10593-016-1918-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-016-1918-3

Keywords

Search

Navigation