Chemistry of Heterocyclic Compounds

, Volume 54, Issue 2, pp 114–121 | Cite as

Synthetic profiles to pyrazolylquinoxalines

Article
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Pyrazolylquinoxalines act as important intermediates for the production of novel derivatives with potential biological applications. The current review covers the synthesis of 2(3)-(pyrazol-1(3(5),4)-yl)quinoxalines published from 1978 until present.

Keywords

pyrazoles pyrazolylquinoxalines quinoxalines 

Notes

The project was supported by King Saud University, Deanship of Scientific Research, Research Chairs.

References

  1. 1.
    Pereira, J. A.; Pessoa, A. M.; Cordeiro, M. N. D. S.; Fernandes, R.; Prudêncio, C.; Noronha, J. P.; Vieira, M. Eur. J. Med. Chem. 2015, 97, 664.CrossRefGoogle Scholar
  2. 2.
    Nageswar, Y. V. D.; Reddy, K. H. V.; Ramesh, K.; Murthy, S. N. Org. Prep. Proced. Int. 2013, 45, 1.CrossRefGoogle Scholar
  3. 3.
    Yuan, J.; Ouyang, J.; Cimrová, V.; Leclerc, M.; Najari, A.; Zou, Y. J. Mater. Chem. C 2017, 5, 1858.CrossRefGoogle Scholar
  4. 4.
    Achelle, S.; Baudequin, C.; Plé, N. Dyes Pigm. 2013, 98, 575.CrossRefGoogle Scholar
  5. 5.
    El Newahie, A. M. S.; Ismail, N. S. M.; Abou El Ella, D. A. K.; Abouzid, A. M. Arch. Pharm. Chem. Life Sci. 2016, 349, 309.CrossRefGoogle Scholar
  6. 6.
    Cheng, G.; Sa, W.; Cao, C.; Guo, L.; Hao, H.; Liu, Z.; Wang, X.; Yuan, Z. Front Pharmacol. 2016, 7, 64.Google Scholar
  7. 7.
    Pereira, J. A.; Pessoa, A. M.; Cordeiro, M. N.; Fernandes, R.; Prudêncio, C.; Noronha, J. P.; Vieira M. Eur. J Med. Chem. 2015, 97, 664.CrossRefGoogle Scholar
  8. 8.
    Ajani, O. O. Eur. J. Med. Chem. 2014, 85, 688.CrossRefGoogle Scholar
  9. 9.
    González, M.; Cerecetto, H. Expert Opin. Ther. Pat. 2012, 22, 1289.CrossRefGoogle Scholar
  10. 10.
    Dhanaraj, C. J.; Johnson, J.; Joseph, J.; Joseyphus, R. S. J. Coord. Chem. 2013, 66, 1416.CrossRefGoogle Scholar
  11. 11.
    Cherukupalli, S.; Karpoormath, R.; Chandrasekaran, B.; Hampannavar, G. A.; Thapliyal, N.; Palakollu, V. N. Eur. J. Med. Chem. 2017, 126, 298.CrossRefGoogle Scholar
  12. 12.
    Khan, M. F.; Alam, M. M.; Verma, G.; Akhtar, W.; Akhter, M.; Shaquiquzzaman, M. Eur. J. Med. Chem. 2016, 120, 170.CrossRefGoogle Scholar
  13. 13.
    Havrylyuk, D.; Roman, O.; Lesyk, R. Eur. J. Med. Chem. 2016, 113, 145.CrossRefGoogle Scholar
  14. 14.
    Kaur, K.; Kumar, V.; Gupta, G. K. J. Fluorine Chem. 2015, 178, 306.CrossRefGoogle Scholar
  15. 15.
    Keri, R. S.; Chand, K.; Ramakrishnappa, T.; Nagaraja, B. M. Arch. Pharm. Chem. Life Sci. 2015, 348, 299.CrossRefGoogle Scholar
  16. 16.
    Mamedov, V. A. Quinoxalines: Synthesis, Reactions, Mechanisms and Structure; Springer: Heidelberg, 2016.Google Scholar
  17. 17.
    Aggarwal, R.; Sumran, G.; Kumar, R.; Singh, S. P. ARKIVOC 2007, (xv), 292.Google Scholar
  18. 18.
    Aggarwal, R.; Masan, E.; Sumran, G. Synth. Commun. 2013, 43, 1842.CrossRefGoogle Scholar
  19. 19.
    Eakta; Aggarwal, R.; Sumran, G. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2013, 52B, 273.Google Scholar
  20. 20.
    Shiho, D.; Tagami, S. J. Am. Chem. Soc. 1960, 82, 4044.CrossRefGoogle Scholar
  21. 21.
    Wojciechowski, L. PL Patent 72990.Google Scholar
  22. 22.
    El Massry, A. M. Heterocycl. Commun. 1999, 5, 555.CrossRefGoogle Scholar
  23. 23.
    Al-Marhabi, A. R.; Abbas, H.-A. S.; Ammar, Y. A. Molecules 2015, 20, 19805.CrossRefGoogle Scholar
  24. 24.
    Abbas, H. A.; Al-Marhabi, A. R.; Eissa, S. I.; Ammar, Y. A. Bioorg. Med. Chem. 2015 23, 6560.CrossRefGoogle Scholar
  25. 25.
    Issa, D. A. E.; Habib, N. S.; Abdel Wahab, A. E. Med. Chem. Commun. 2015, 6, 202.CrossRefGoogle Scholar
  26. 26.
    Ajani, O. O.; Obafemi, C. A.; Ikpo, C. O.; Ogunniran, K. O.; Nwinyi, O. C. Chem. Heterocycl. Compd. 2009, 45, 1370. [Khim. Geterotsikl. Soedin. 2009, 1703.]Google Scholar
  27. 27.
    Rashed, N.; El Massry, A. M.; El Ashry, E. S. H.; Amer, A.; Zimmer, H. J. Heterocycl. Chem. 1990, 27, 691.CrossRefGoogle Scholar
  28. 28.
    Kim, H. S.; Lee, S. U.; Jeong, W. Y.; Han, S. W.; Kim, D. I.; Kurasawa, Y. J. Korean Chem. Soc. 2001, 45, 318.Google Scholar
  29. 29.
    Atta, K. F.; El-Massry, A.; Abdel Hamid, H.; El Ashry, E. H.; Amer, A. J. Heterocycl. Chem. 1994, 31, 549.CrossRefGoogle Scholar
  30. 30.
    Kim, H. S.; Kwag, S. T. J. Korean Chem. Soc. 2000, 44, 229.Google Scholar
  31. 31.
    Kim, H. S.; Kwag, S. T.; Choi, K. O.; Okamoto, Y.; Kajiwara, S.; Fujiwara, N.; Kurasawa, Y. J. Heterocycl. Chem. 2000, 37, 103.CrossRefGoogle Scholar
  32. 32.
    Gad, L. M. Mansoura J. Pharm. Sci. 1994, 10, 237; Chem. Abstr. 1995, 123, 9412.Google Scholar
  33. 33.
    Soliman, A. M.; Amer, A. A. Synth. Commun. 2012, 42, 1401.CrossRefGoogle Scholar
  34. 34.
    Wojciechowski, L. PL Patent 72674.Google Scholar
  35. 35.
    Kim, H. S.; Jeong, W. Y.; Choi, K. O.; Lee, S. U.; Kwag, S. T.; Lee, M. K. J. Korean Chem. Soc. 2002, 46, 37.CrossRefGoogle Scholar
  36. 36.
    Aggarwal, R.; Kumar, R. Synth. Commun. 2009, 39, 2169.CrossRefGoogle Scholar
  37. 37.
    Kurasawa, Y.; Takano, A.; Kato, K.; Takada, A.; Kim, H. S.; Okamoto, Y. J. Heterocycl. Chem. 1996, 33, 757.CrossRefGoogle Scholar
  38. 38.
    Eiden, F.; Bachmann, G. Arch. Pharm. 1973, 306, 401.CrossRefGoogle Scholar
  39. 39.
    Sarodnick, G.; Kempter, G. Ger. (East) Patent DD 291999.Google Scholar
  40. 40.
    Sarodnick, G. Chem.-Ztg. 1991, 115, 217; Chem. Abstr. 1991, 115, 256116.Google Scholar
  41. 41.
    Ferfra, S.; Ahabchane, N. H.; Garrigues, B.; Essassi, E. C. R. Acad. Sci., Ser. IIc: Chim. 2001, 4, 905.Google Scholar
  42. 42.
    Doumbia, M. L.; Bouhfid, R.; Ahabchane, N. H.; Essassi, E. ARKIVOC 2008, (xiii), 36.Google Scholar
  43. 43.
    Rashed, N.; Abdel Hamid, H.; El-Ashry, E. S. H. Alexandria J. Pharm. Sci. 1993, 7, 47.Google Scholar
  44. 44.
    Rashed, N.; Abdel Hamid, H. Shoukry, M. Heterocycles 1993, 36, 961.CrossRefGoogle Scholar
  45. 45.
    Abdel Hamid, H. Alexandria J. Pharm. Sci. 1992, 6, 59.Google Scholar
  46. 46.
    Awad, L. F.; Abdel Hamid, H.; Rashed, N. Alexandria J. Pharm. Sci. 1991, 5, 14.Google Scholar
  47. 47.
    El Ashry, E. S. H.; El Kilany, Y.; Abdel Hamid, H. Gazz. Chim. Ital. 1986, 116, 721.Google Scholar
  48. 48.
    El Ashry, E. S. H.; El Kholy, I. E.; El Kilany, Y. Carbohydr. Res. 1978, 60, 303.CrossRefGoogle Scholar
  49. 49.
    El Ashry, E. S. H.; El Kholy, I. E.; El Kilany, Y. Carbohydr. Res. 1978, 64, 81.CrossRefGoogle Scholar
  50. 50.
    El Ashry, E. S. H.; Abdel Rahman, M.; Labib, G. H.; El-Massry, A. M.; Moft, A. Carbohydr. Res. 1986, 152, 339.CrossRefGoogle Scholar
  51. 51.
    El Kilany, Y.; Rashed, N.; Mansour, M.; Abdel Rahman, M.; El Ashry, E. S. H. J. Carbohydr. Chem. 1988, 7, 199.CrossRefGoogle Scholar
  52. 52.
    Mousaad, A.; Awad, L.; El Shimy, N.; El Ashry, E. S. H. J. Carbohydr. Chem. 1989, 8, 773.CrossRefGoogle Scholar
  53. 53.
    Somogyi, L. Carbohydr. Res. 1992, 229, 89.CrossRefGoogle Scholar
  54. 54.
    Awad, L. F. Carbohydr. Res. 2000, 326, 34.CrossRefGoogle Scholar
  55. 55.
    Abdel Hamid, H. M. Carbohydr. Res. 2003, 338, 2301.CrossRefGoogle Scholar
  56. 56.
    Atta, K. F. M.; El Ashry, E. H. J. Heterocycl. Chem. 2011, 48, 1216.CrossRefGoogle Scholar
  57. 57.
    El Ashry, E. S. H.; Atta, K. F.; Aboul-Ela, S.; Beldi, R. J. Carbohydr. Chem. 2007, 26, 1.CrossRefGoogle Scholar
  58. 58.
    Zalesov, V. V.; Vyaznikova, N. G.; Andreichikov, Y. S. Zh. Org. Khim. 1995, 31, 1213.Google Scholar
  59. 59.
    Kurasawa, Y.; Takada, A. Heterocycles 1980, 14, 281.CrossRefGoogle Scholar
  60. 60.
    Kurasawa, Y.; Takada, A. Chem. Pharm. Bull. 1981, 29, 2871.CrossRefGoogle Scholar
  61. 61.
    Pissot-Soldermann, C.; Gerspacher, M.; Furet, P.; Gaul, C.; Holzer, P.; McCarthy, C.; Radimerski, T.; Regnier, C. H.; Baffert, F.; Drueckes, P.; Tavares, G. A.; Vangrevelinghe, E.; Blasco, F.; Ottaviani, G.; Ossola, F.; Scesa, J.; Reetz, J. Bioorg. Med. Chem. Lett. 2010, 20, 2609.CrossRefGoogle Scholar

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Authors and Affiliations

  1. 1.Department of Chemistry, College of Science and HumanitiesShaqra UniversityDuwadimiSaudi Arabia
  2. 2.Applied Organic Chemistry DepartmentNational Research CentreGizaEgypt
  3. 3.Cornea Research Chair, Department of Optometry, College of Applied Medical SciencesKing Saud UniversityRiyadhSaudi Arabia

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