Skip to main content
SpringerLink
Log in

Synthesis of (1H-1,2,3-Triazol-1-yl)acetic Acid Derivatives

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A convenient synthetic approach to (1H-1,2,3-triazol-1-yl)acetic acid derivatives via the reaction of azidoacetamides with β-ketoesters and acetylacetone is proposed. Based on this strategy, 1,5-disubstituted 1,2,3-triazoles were prepared from available reagents under metal-free conditions. A one-pot protocol for the synthesis of (5-methyl-1H-1,2,3-triazol-1-yl)acetamides derived from N-substituted chloroacetamides is developed.

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

Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Horne, W.S., Yadav, M.K., Stout, C.D., and Ghadiri, M.R., J. Am. Chem. Soc., 2004, vol. 126, p. 15366. https://doi.org/10.1021/ja0450408

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Sangshetti, J.N., Nagawade, R.R., and Shinde, D.B., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 3564. https://doi.org/10.1016/j.bmcl.2009.04.134

    Article  CAS  PubMed  Google Scholar 

  3. Sangshetti, J.N. and Shinde, D.B., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 742. https://doi.org/10.1016/j.bmcl.2009.11.048

    Article  CAS  PubMed  Google Scholar 

  4. Sangshetti, J.N., Chabukswar, A.R., and Shinde, D.B., Bioorg. Med. Chem. Lett., 2011, vol. 21, p. 444. https://doi.org/10.1016/j.bmcl.2010.10.120

    Article  CAS  PubMed  Google Scholar 

  5. Boechat, N., Ferreira, V.F., Ferreira, S.B., Ferrera, M.D.L.G., da Silva, F.C., Bastos, M.M., Costa, M.S., Lourenço, M.C.S., Pinto, A.C., Krettli, A.U., Aguiar, A.C., Teixeira, B.M., da Silva, N.V., Martins, P.R.C., Bezerra, F.A.F.M., Camilo, A.L.S., da Silva, G.P., and Costa, C.C.P., J. Med. Chem., 2011, vol. 54, p. 5988. https://doi.org/10.1021/jm2003624

    Article  CAS  PubMed  Google Scholar 

  6. de Lourdes, M., Ferreira, G., Pinheiro, L.C.S., Santos-Filho, O.A., Pecanha, M.D.S., Sacramento, C.Q., Machado, V., Ferreira, V.F., Souza, T.M.L., and Boechat, N., Med. Chem. Res., 2014, vol. 23, p. 1501. https://doi.org/10.1007/s00044-013-0762-6

    Article  CAS  Google Scholar 

  7. Pokhodylo, N.T., Shyyka, O.Ya, Skrobala, V.E., and Matiychuk, V.S., Clin. Pharmacy, Pharmacother. Med. Standardization, 2012, vol. 16–17, p. 92 (in ukrainian).

    Google Scholar 

  8. Pokhodylo, N., Shyyka, O., and Matiychuk, V., Sci. Pharm., 2013, vol. 81, p. 663. https://doi.org/10.3797/scipharm.1302-04

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Pokhodylo, N.T., Shyyka, O.Ya., and Matiychuk, V.S., Med. Chem. Res., 2014, vol. 23, p. 2426. https://doi.org/10.1007/s00044-013-0841-8

    Article  CAS  Google Scholar 

  10. Pokhodylo, N.T., Shyyka, O.Ya., and Finiuk, N.S., Biopolym. Cell., 2019, vol. 35, p. 321. https://doi.org/10.7124/bc.000A0F

    Article  Google Scholar 

  11. Sugawara, A., Sunazuka, T., Hirose, T., Nagai, K., Yamaguchi, Y., Hanaki, H., Sharpless, K.B., and Omura, S., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 6340. https://doi.org/10.1016/j.bmcl.2007.08.068

    Article  CAS  PubMed  Google Scholar 

  12. Gao, G., Smiesko, M., Schwardt, O., Gaethje, H., Kelm, S., Vedani, A., and Ernst, B., Bioorg. Med. Chem. 2007, vol. 15, p. 7459. https://doi.org/10.1016/j.bmc.2007.07.033

  13. Wallace, G.A., Breinlinger, E.C., Cusack, K.P., Fix-Stenzel, S.R., Gordon, T.D., Hobson, A.D., Hayes, M.E., Ansell, G.K., and Grongsaard, P., WO Patent Appl. no. WO 2008079382; Chem. Abstr., 2008, vol. 149, no. 128619.

  14. Fortin, R., Lachance, N., Li Chun, S., and Tranmer, G., WO Patent Appl. no. WO 2011047481; Chem. Abstr., 2011, vol. 154, no. 513424.

  15. Lolk, L., Jepsen, A.S., Nielsen, H., Steffansen, S.I., Sparving, L., Nielsen, A.B., Nielsen, P., Pohlsgaard, J., Hansen, L.H., and Vester, B., J. Med. Chem., 2008, vol. 51, p. 4957. https://doi.org/10.1021/jm800261u

    Article  CAS  PubMed  Google Scholar 

  16. Corrales, R.C.N.R., de Souza, N.B., Pinheiro, L.S., Abramo, C., Coimbra, E.S., and da Silva, A.D., Biomed. Pharmacother., 2011, vol. 65, p. 198. https://doi.org/10.1016/j.biopha.2010.10.013

    Article  CAS  PubMed  Google Scholar 

  17. Sun, L., Huang, T., Dick, A., Meuser, M.E., Zalloum, W.A., Chen, C.H., Ding, X., Gao, P., Cocklin, S., Lee, K.-H., Zhan, P., and Liu, X., Eur. J. Med. Chem., 2020, vol. 190, p. 112085. https://doi.org/10.1016/j.ejmech.2020.112085

    Article  CAS  PubMed  Google Scholar 

  18. Pokhodylo, N.T., Matiichuk, V.S., and Obushak, M.D., Russ. J. Org. Chem., 2017, vol. 53, p. 481. https://doi.org/10.1134/S1070428017030332

    Article  CAS  Google Scholar 

  19. Pokhodylo, N.T., Savka, R.D., and Obushak, M.D., Russ. J. Org. Chem., 2017, vol. 53, p. 734. https://doi.org/10.1134/S1070428017050141

    Article  CAS  Google Scholar 

  20. Pokhodylo, N.T., Shyyka, O.Ya., Goreshnik, E.A., and Obushak, M.D., ChemistrySelect, 2020, vol. 5, p. 260. https://doi.org/10.1002/slct.201904688

    Article  CAS  Google Scholar 

  21. Pokhodylo, N.T., Shyyka, O.Ya., Matiychuk, V.S., Obushak, M.D., and Pavlyuk, V.V., ChemistrySelect, 2017, vol. 2, p. 5871. https://doi.org/10.1002/slct.201700577

    Article  CAS  Google Scholar 

  22. Pokhodylo, N.T., Shyyka, O.Ya., and Obushak, M.D., Chem. Heterocycl. Сompd., 2018, vol. 54, p. 773. https://doi.org/10.1007/s10593-018-2348-1

    Article  CAS  Google Scholar 

  23. Pokhodylo, N.T. and Obushak, M.D., Russ. J. Org. Chem., 2019, vol. 55, p. 1241. https://doi.org/10.1134/S107042801908027X

    Article  CAS  Google Scholar 

  24. Pokhodylo, N.T., Shyyka, O.Y., Savka, R.D., and Obushak, M.D., Russ. J. Org. Chem., 2018, vol. 54, p. 1090. https://doi.org/10.1134/S1070428018070205

    Article  CAS  Google Scholar 

  25. Arshad, M., Bhat, A.R., Pokharel, S., Kim, J.-E., Lee, E.J., Athar, F., and Choi, I., Eur. J. Med. Chem., 2014, vol. 71, p. 229. https://doi.org/10.1016/j.ejmech.2013.11.008

    Article  CAS  PubMed  Google Scholar 

  26. Tam, A., Arnold, U., Soellner, M.B., and Raines, R.T., J. Am. Chem. Soc., 2007, vol. 129, p. 12670. https://doi.org/10.1021/ja075865s

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Boteju, L.W., Zalewska, T., Yamamura, H.I., and Hruby, V.J., Bioorg. Med. Chem. Lett., 1993, vol. 3, p. 2011. https://doi.org/10.1016/S0960-894X(01)81005-2

    Article  CAS  Google Scholar 

  28. Stanley, N.J., Abell, A.D., Pedersen, D.S., Nielsen, B., Kvist, T., Mathiesen, J.M., Braeuner-Osborne, H., and Taylor, D.K., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 7512. https://doi.org/10.1016/j.bmcl.2010.09.139

    Article  CAS  PubMed  Google Scholar 

  29. Johansson, J.R., Lincoln, P., Norden, B., and Kann, N., J. Org. Chem., 2011, vol. 76, p. 2355. https://doi.org/10.1021/jo200134a

    Article  CAS  PubMed  Google Scholar 

  30. Pokhodylo, N.T. Savka, R.D., Matiichuk, V.S., and Obushak, N.D., Russ J. Gen. Chem., 2009, vol. 79, p. 309. https://doi.org/10.1134/S1070363209020248

    Article  CAS  Google Scholar 

  31. Huckin, S.N. and Weiler, L., J. Am. Chem. Soc., 1974, vol. 96, p. 1082. https://doi.org/10.1021/ja00811a023

    Article  CAS  Google Scholar 

  32. Deshayes, C., Chabannet, M., and Gelin, S., J. Heterocycl. Chem., 1986, vol. 23, p. 1595. https://doi.org/10.1002/jhet.5570230567

    Article  CAS  Google Scholar 

  33. Kumar, S., Namkung, W., Verkman, A.S., and Sharma, P.K., Bioorg. Med. Chem., 2012, vol. 20, p. 4237. https://doi.org/10.1016/j.bmc.2012.05.074

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  34. Fabre, B., Pícha, J., Vaněk, V., Selicharová, I., Chrudinová, M., Collinsová, M., Žáková, L., Buděšínský, M., and Jiráček, J., ACS Comb. Sci., 2016, vol. 18, p. 710. https://doi.org/10.1021/acscombsci.6b00132

    Article  CAS  PubMed  Google Scholar 

  35. Froyen, P., Phosphorus Sulfur Silicon Relat. Elem., 1991, vol. 63, p. 283. https://doi.org/10.1080/10426509108036831

    Article  Google Scholar 

  36. Forster, M.O. and Fierz, H.E., J. Chem. Soc., Trans., 1908, vol. 93, p. 1859. https://doi.org/10.1039/CT9089301859

    Article  CAS  Google Scholar 

  37. Forster, M.O. and Müller, R., J. Chem. Soc., Trans., 1909, vol. 95, p. 191. https://doi.org/10.1039/CT9099500191

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ivan Franko National University of Lviv, 79005, Lviv, Ukraine

    N. T. Pokhodylo, R. D. Savka & M. D. Obushak

Authors
  1. N. T. Pokhodylo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. D. Savka
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. D. Obushak
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. D. Obushak.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pokhodylo, N.T., Savka, R.D. & Obushak, M.D. Synthesis of (1H-1,2,3-Triazol-1-yl)acetic Acid Derivatives. Russ J Org Chem 56, 1421–1431 (2020). https://doi.org/10.1134/S1070428020080138

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020080138

Keywords:

Search

Navigation