Skip to main content
SpringerLink
Log in

2-(Azolyl)anilines: methods of synthesis, cyclocondensations, and biological properties

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

This review offers summary and analysis of the data on the synthesis of 2-(azolyl)anilines published from 1942 to 2016. It is shown, that they act as effective 1,5-nucleophiles in cyclocondensation reactions. Besides, biological activity data on 2-(azolyl)anilines and their derivatives are reported.

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

Similar content being viewed by others

References

  1. Cass, W. J. Am. Chem. Soc. 1942, 64, 785.

    Article  CAS  Google Scholar 

  2. Domány, G.; Gizur, T.; Gere, A.; Takács-Novák, K.; Farsang, G.; Ferenczy, G. G.; Tárkányi, G.; Demeter, M. Eur. J. Med. Chem. 1998, 33, 181.

    Article  Google Scholar 

  3. Speake, J. D.; Navas, F.; Bishop, M. J.; Garrison, D. T.; Bigham, E. C.; Hodson, S. J.; Saussy, D. L.; Liacos, J. A.; Irving, P. E.; Sherman, B. W. Bioorg. Med. Chem. Lett. 2003, 13, 1183.

    Article  CAS  Google Scholar 

  4. Janjić, M.; Prebil, R.; Grošelj, U.; Kralj, D.; Malavašič, Č.; Golobič, A.; Stare, K.; Dahmann, G.; Stanovnik, B.; Svete, J. Helv. Chim. Acta 2011, 94, 1703.

    Article  Google Scholar 

  5. Abramov, M.; Dehaen, W.; D'hooge, B.; Petrov, M.; Smeets, S.; Toppet, S.; Voets, M. Tetrahedron 2000, 56, 3933.

    Article  CAS  Google Scholar 

  6. Biagi, G.; Giorgi, I.; Livi, O.; Manera, C.; Scartoni, V.; Barili, P. J. Heterocycl. Chem. 1997, 34, 845.

    Article  CAS  Google Scholar 

  7. Saha, B.; Sharma, S.; Sawant, D.; Kundu, B. Tetrahedron 2008, 64, 8676.

    Article  CAS  Google Scholar 

  8. Koguro, K.; Oga, T.; Mitsui, S.; Orita, R. Synthesis 1998, 910.

  9. Lang, L.; Li, B.; Liu, W.; Jiang, L.; Xu, Z.; Yin, G. Chem. Commun. 2010, 448.

  10. Qi, G.; Dai, Y. Chin. Chem. Lett. 2010, 21, 1029.

    Article  CAS  Google Scholar 

  11. Qi, G.; Liu, W.; Bei, Z. Chinese J. Chem. 2011, 29, 131.

    CAS  Google Scholar 

  12. Ai, M.; Lang, L.; Li, B.; Xu, Z. Chem. Lett. 2012, 41, 814.

    Article  CAS  Google Scholar 

  13. Valgeirsson, J.; Nielsen, E. Ø; Peters, D.; Mathiesen, C.; Kristensen, A. S.; Madsen, U. J. Med. Chem. 2004, 47, 6948.

    Article  CAS  Google Scholar 

  14. Fujisawa, T.; Ichiyanagi, T.; Shimizu, M. Tetrahedron Lett. 1995, 36, 5031.

    Article  CAS  Google Scholar 

  15. Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. Tetrahedron 1997, 53, 9599.

    Article  CAS  Google Scholar 

  16. Wolińska, E. Tetrahedron 2013, 69, 7269.

    Article  Google Scholar 

  17. Ge, H.; Liu, P.; Li, X.; Sun, W.; Li, J.; Yang, B.; Shi, Z. Tetrahedron 2013, 69, 6591.

    Article  CAS  Google Scholar 

  18. Li, X.; Zhou, B.; Zhang, J.; She, M.; An, S.; Ge, H.; Li, C.; Yin, B.; Li, J.; Shi, Z. Eur. J. Org. Chem. 2012, 1626.

  19. Korshin, E.; Sabirova, L.; Levin, Y. Synthesis 2012, 3512.

  20. Antilla, J.; Baskin, J.; Barder, T.; Buchwald, S. J. Org. Chem. 2004, 69, 5578.

    Article  CAS  Google Scholar 

  21. Du, S.; Tian, Z.; Yang, D.; Li, X.; Li, H.; Jia, C.; Che, C.; Wang, M.; Qin, Z. Molecules 2015, 20, 8395.

    Article  CAS  Google Scholar 

  22. Wanniarachchi, S.; Liddle, B. J.; Lindeman, S. V.; Gardinier, J. R. J. Organomet. Chem. 2011, 696, 3623.

    Article  CAS  Google Scholar 

  23. Liddle, B. J; Silva, R. M.; Morin, T. J.; Macedo, F. P.; Shukla, R. R; Lindeman, S. V.; Gardinier, J. R. J. Org. Chem. 2007, 72, 5637.

    Article  CAS  Google Scholar 

  24. Morin, T. J.; Lindeman, S. V.; Gardinier, J. R. Eur. J. Inorg. Chem. 2009, 104.

  25. Liu, Y.; Liu, Y.; Ma, X.; Liu, P.; Xie, J.; Dai, B. Chinese Chem. Lett. 2014, 25, 775.

    Article  CAS  Google Scholar 

  26. Faizulla G. K. US Patent 4020083.

  27. Molina, P.; Arques, A.; Alias, M. A.; Llamas Saiz, A. L.; de la Concepción Foces-Foces, M. Liebigs Ann. Chem. 1989, 1055.

  28. Antipenko, L.; Karpenko, A.; Kovalenko, S.; Katsev, A.; Komarovska-Porokhnyavets, E.; Novikov, V.; Chekotilo, A. Chem. Pharm. Bull. 2009, 57, 580.

    Article  CAS  Google Scholar 

  29. Kovalenko, S. І.; Voloshina, V. O.; Karpenko, O. V. Zh. Org. Farm. Khim. 2010, 8(2), 48.

    CAS  Google Scholar 

  30. Bіlyi, A. K.; Kovalenko, S. I.; Pryhod'ko, O. B.; Emec', T. І. Zaporozhskiy Med. Zh. 2013, (2), 83.

  31. Antypenko, O. M.; Kovalenko, S. I.; Karpenko, O. V. Synth. Commun. 2016, 46, 551.

    Article  CAS  Google Scholar 

  32. Kiselyov, A. S.; Piatnitski, E.; Milligan, D.; Ouyang, X. Chem. Biol. Drug. Des. 2007, 69, 331.

    Article  CAS  Google Scholar 

  33. Hunt, D. Org. Prep. Proc. Int. 2007, 39, 93.

    Article  CAS  Google Scholar 

  34. Hu, F.; Xie, S.; Jiang, L.; Shen, Z. RSC Adv. 2014, 4, 59917.

    Article  CAS  Google Scholar 

  35. Shang, M.; Sun, S.; Dai, H.; Yu, J. J. Amer. Chem. Soc. 2014, 136, 3354.

    Article  CAS  Google Scholar 

  36. Rouhani, M.; Ramazani, A.; Joo, S. Ultrason. Sonochem. 2014, 21, 262.

    Article  CAS  Google Scholar 

  37. Bahekar, R. H.; Ram Rao, A. R. Arzneim. Forsch. 2001, 51, 284.

    CAS  Google Scholar 

  38. Buettelmann, B.; Knust, H.; Thomas, A. US Patent 7507729.

  39. Pařík, P.; Jansa, J.; Holešová, S.; Marek, A.; Klimešová, V. J. Heterocycl. Chem. 2013, 50, 903.

    Article  Google Scholar 

  40. Black, D. S.; Deacon, G. B.; Edwards, G. L. Aust. J. Chem. 1991, 44, 1771.

    Article  CAS  Google Scholar 

  41. Vlaar, T.; Bensch, L.; Kraakman, J.; Vande Velde, C.; Maes, B.; Orru, R.; Ruijter, E. Adv. Synth. Catal. 2014, 356, 1205.

    Article  CAS  Google Scholar 

  42. Subramanian, P.; Kaliappan, K. Eur. J. Org. Chem. 2014, 5986.

  43. Fransis, J. E.; Gelotte, K. O. US Patent 4713383.

  44. Francis, J. E.; Cash, W. D.; Barbaz, B. S.; Bernard, P. S.; Lovell, R. A.; Mazzenga, G. C.; Friedmann, R. C.; Hyun, J. L.; Braunwalder, A. F. J. Med. Chem. 1991, 34, 281.

    Article  CAS  Google Scholar 

  45. Gusev, A. N.; Shul'gin, V. F.; Konnic, O. V.; Meshkova, S. B.; Aleksandrov, G. A.; Kiskin, M. A.; Eremenko, I. L.; Linert, W. Inorg. Chim. Acta 2011, 376, 509.

    Article  CAS  Google Scholar 

  46. Gusev, A. N.; Shul'gin, V. F.; Kiskin, M. A.; Eremenko, I. L. Russ. J. Coordin. Chem. 2011, 37, 589. [Koord. Khim. 2011, 37, 589.]

  47. Gatta, F.; Del Giudice, M. R.; Borioni, A. J. Heterocycl. Chem. 1993, 30, 11.

    Article  CAS  Google Scholar 

  48. Mustazza, C.; Borioni, A., Sestili, I.; Sbraccia, M.; Rodomonte, A.; Ferretti, R.; Del Giudice, M. R. Chem. Pharm. Bull. 2006. 54, 611.

    Article  CAS  Google Scholar 

  49. Balo, C.; López, C.; Brea, J.; Fernánde, F.; Caamaño, O. Chem. Pharm. Bull. 2007, 55, 372.

    Article  CAS  Google Scholar 

  50. Gelotte, K. O.; Mason, D. N.; Meckler, H. H.; Shieh, W.-C.; Starkey, C. M. J. Heterocycl. Chem. 1990, 27, 1549.

    Article  CAS  Google Scholar 

  51. Voloshina, V. O.; Litvinenko, M. O.; Sapegyn, I. D.; Berest, G. G.; Kovalenko, S. I.; Babanin, A. A.; Siniak, R. S. Med. Chem. (Ternopol, Ukr.) 2010, 12, 98.

    Google Scholar 

  52. Kovalenko, S. I.; Voloshina, V. O.; Litvinenko, M. O.; Berest, G. G.; Zubatyuk, R. I. Zh. Org. Farm. Khim. 2010, 8(4), 62.

    CAS  Google Scholar 

  53. Kholodnyak, S. V.; Schabelnyk, K. P.; Kovalenko, S. I.; Zhernova, G. О.; Trzhetsinsky, S. D. Aktualni Pitannya Farmatsevtichnoi i Medichnoi Nauki ta Praktiki 2015, (2), 9.

    Google Scholar 

  54. Kovalenko, S. I.; Voloshina, V. O.; Biliy, A. K. Berest, G. G.; Zubatyuk, R. I. Zh. Org. Farm. Khim. 2010, 8(1), 30.

    CAS  Google Scholar 

  55. Biliy, A. K.; Antypenko, L. M.; Ivchuk, V. V.; Kamishny, O. M.; Polishchuk, N. M.; Kovalenko, S. I. ChemPlusChem 2015, 80, 980.

    Article  Google Scholar 

  56. Britton, T. C.; Wagner E. R. US Patent 4286090.

  57. Antypenko, L. M.; Kovalenko, S. I.; Antypenko, O. M.; Katsev, A. M.; Achkasova, O. M. Sci. Pharm. 2013, 81, 15.

    Article  CAS  Google Scholar 

  58. Antypenko, O.; Antypenko, L.; Kovalenko, S.; Katsev, A.; Achkasova, O. M. Arab. J. Chem. 2016, 9, 792.

    Article  CAS  Google Scholar 

  59. Starosyla, S. A.; Protopopov, M. B.; Voskoboynik, O. Yu.; Nosulenko, I. S.; Antypenko, L. M.; Antypenko, O. M.; Fesun, I. M.; Kovalenko, S. I.; Yarmolyuk, S. M. Ukr. Bioorg. Acta 2014, 12(1), 12.

    CAS  Google Scholar 

  60. Antypenko, O. M.; Kovalenko, S. I.; Zhernova, G. О. Sci. Pharm. 2016, 84, 233

    Article  CAS  Google Scholar 

  61. Jia, F.; Zhou, Z.; Xu, C.; Cai, Q.; Li, D.; Wu, A. Org. Lett. 2015, 17, 4236.

    Article  CAS  Google Scholar 

  62. Kholodnyak, S. V.; Schabelnyk, K. P.; Voskoboynik, O. Yu.; Berest, G. G.; Kovalenko, S. I. Zh. Org. Farm. Khim. 2015, 13(4), 50.

    CAS  Google Scholar 

  63. Kholodnyak, S. V.; Schabelnyk, K. P.; Voskoboynik, O. Yu.; Antypenko, L. M.; Berest, G. G.; Kovalenko, S. I. Zh. Org. Farm. Khim. 2016, 14(1), 24.

    Google Scholar 

  64. Kholodnyak, S. V.; Schabelnyk, K. P.; Voskoboynik, O. Yu.; Antypenko, L. M.; Kovalenko, S. I.; Palchykov, V. O.; Okovyty, S. I.; Shishkina, S. V. Zh. Org. Farm. Khim. 2016, 14(3), 24.

    Google Scholar 

  65. Bіliy, A. K.; Kovalenko, S. I.; Antypenko, L. M.; Kamishny, G. M.; Polishchuk, N. M. Aktualni Pitannya Farmatsevtichnoi i Medichnoi Nauki ta Praktiki 2013, (2), 80.

    Google Scholar 

  66. Bіliy, A. K.; Kovalenko, S. I.; Holodnyak, S. V.; Prikhodko, D. B.; Yemets, T. I. In 9th International Conference in Applied Biotechnology “Phytohormones, Humic Substances and other Biologically Active Compounds for Agriculture, Human Health and Environmental Protection (daRostim)”, 7–10 October, 2013, Lviv, Ukraine; Lviv Polytechnic National University, 2013, p. 3.

  67. Voloshina, V. A.; Sapegin, I. D.; Kovalenko, S. I.; Berest, G. G.; Biliy, A. K. Zaporozhskiy Med. Zh. 2009, 11(4), 72

    Google Scholar 

  68. Chassot, L.; Braun, H. J. US Patent 20030115683.

  69. von Deyn, W.; Gebhardt, J.; Rack, M.; Lochtman, R.; Götz, N.; Keil, M.; Witschel, M.; Hagen, H.; Misslitz, U.; Baumann, E. US Patent 6469176.

Download references

Author information

Authors and Affiliations

  1. Zaporizhzhia State Medical University, 26, Mayakovsky Ave., Zaporizhzhia, 69035, Ukraine

    Oleksii M. Antypenko, Sergiy V. Kholodnyak, Konstantyn P. Schabelnyk, Lyudmyla M. Antypenko & Sergiy I. Kovalenko

Authors
  1. Oleksii M. Antypenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sergiy V. Kholodnyak
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Konstantyn P. Schabelnyk
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lyudmyla M. Antypenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Sergiy I. Kovalenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Sergiy I. Kovalenko.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(3), 292–309

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Antypenko, O.M., Kholodnyak, S.V., Schabelnyk, K.P. et al. 2-(Azolyl)anilines: methods of synthesis, cyclocondensations, and biological properties. Chem Heterocycl Comp 53, 292–309 (2017). https://doi.org/10.1007/s10593-017-2051-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2051-7

Keywords

Search

Navigation