Skip to main content
SpringerLink
Log in

Synthesis of 4,5-disubstituted-1H-1,2,3-triazoles

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Two-step procedure, a palladium catalyzed Sonogashira cross-coupling reaction of aroyl chlorides with aryl acetylenes, and 1,3-dipolar cycloaddition of the 1,3-diarylprop-2-yn-1-ones with sodium azide under catalyst free conditions achieved the synthesis of aryl(4-aryl-1H-1,2,3-triazol-5-yl)methanones in moderate-to-good chemical yields (30–90%). The procedures allowed the synthesis of 4,5-disubstituted-1H-1,2,3-triazol scaffolds containing electron-neutral, -withdrawing, or -donating groups.

Graphic abstract

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

Fig. 1
Fig. 2

Similar content being viewed by others

Notes

  1. Due to the prototropy of 1,2,3-triazoles, the name of structures 7a–7i can be aryl(5-aryl-1H-1,2,3-triazol-4-yl)methanones or aryl(4-aryl-1H-1,2,3-triazol-5-yl)methanones. Herein, we used the former one to be coherent with the number system presented in Table 2.

References

  1. Thirumurugan P, Matosiuk D, Jozwiak K (2013) Chem Rev 113:4905

    Article  CAS  PubMed  Google Scholar 

  2. Gup R, Erer O, Dilek N (2017) J Mol Struct 1129:142

    Article  CAS  Google Scholar 

  3. Dheer D, Singh V, Shankar R (2017) Bioorg Chem 71:30

    Article  CAS  PubMed  Google Scholar 

  4. Li Q, Tan W, Zhang C, Gu G, Guo Z (2016) Int J Biol Macromol 91:623

    Article  CAS  PubMed  Google Scholar 

  5. Kant R, Singh V, Nath G, Awasthi SK, Agarwal A (2016) Eur J Med Chem 124:218

    Article  CAS  PubMed  Google Scholar 

  6. Angajala KK, Vianala S, Macha R, Raghavender M, Thupurani MK, Pathi PJ (2016) SpringerPlus 5:423

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Aneja R, Rashad AA, Li H, Sundaram RVK, Duffy C, Bailey LD, Chaiken I (2015) J Med Chem 58:3843

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Ma L-Y, Wang B, Pang L-P, Zhang M, Wang S-Q, Zheng Y-C, Shao K-P, Xue D-Q, Liu H-M (2015) Bioorg Med Chem Lett 25:1124

    Article  CAS  PubMed  Google Scholar 

  9. Chavan PV, Desal UV, Wadgaonkar PP, Tapase SR, Kodam KM, Choudhari A, Sarkar D (2019) Bioorg Chem 85:475

    Article  CAS  PubMed  Google Scholar 

  10. Bebenek E, Kadela-Tomanek M, Chrobak E, Latocha M, Boryczka S (2018) Med Chem Res 27:2051

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Lal K, Yadav P (2018) Anti-Cancer Med Chem 18:21

    Article  CAS  Google Scholar 

  12. Gregorić T, Sedić M, Grbčić AT, Paravić AT, Pavelić SK, Cetina M, Vianello R, Raić-Malić S (2017) Eur J Med Chem 125:1247

    Article  CAS  PubMed  Google Scholar 

  13. Vantikommu J, Palle S, Reddy PS, Ramanatham V, Khagga M, Pallapothula VR (2010) Eur J Med Chem 45:5044

    Article  CAS  PubMed  Google Scholar 

  14. Madali NR, Penthala NR, Howk K, Ketkar A, Eoff RL, Borrelli MJ, Crooks PA (2015) Eur J Med Chem 103:123

    Article  CAS  Google Scholar 

  15. Schulzeab B, Schubert US (2014) Chem Soc Rev 43:2522

    Article  CAS  Google Scholar 

  16. Johnson JA, Finn MG, Koberstein JT, Turro NJ (2008) Macromol Rapid Commun 29:1052

    Article  CAS  Google Scholar 

  17. Rajalekshmi KM, Jaleel CA, Azooz MM, Panneerselvam R (2009) Adv Biol Res 3:117

    Google Scholar 

  18. Zhang G, Wang Y, Wen X, Ding C, Li Y (2012) Chem Commun 48:2979

    Article  CAS  Google Scholar 

  19. Desai PS, Indorwala NS (2015) Int J Curr Microbiol App Sci 4:928

    CAS  Google Scholar 

  20. Balamurugan S, Yeap G-Y, Mahmood WAK (2014) Liq Cryst 41:776

    Article  CAS  Google Scholar 

  21. Miladinova PM, Konstantinova TN (2015) J Chem Technol Metall 50:229

    CAS  Google Scholar 

  22. Li H, Aneja R, Chaiken I (2013) Molecules 18:9797

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Muller T, Braese S (2011) Angew Chem Int Ed 50:11844

    Article  CAS  Google Scholar 

  24. Astruc D, Liang L, Rapakousiou A, Ruiz J (2012) Acc Chem Res 45:630

    Article  CAS  PubMed  Google Scholar 

  25. Huisgen R, Guenter S, Leander M (1967) Chem Ber 100:2494

    Article  CAS  Google Scholar 

  26. Kolb HC, Finn MG, Sharpless KB (2001) Angew Chem Int Ed 40:2004

    Article  CAS  Google Scholar 

  27. Ponpandian T, Muthusubramanian S (2012) Tetrahedron Lett 53:59

    Article  CAS  Google Scholar 

  28. Chai H, Guo R, Yin W, Cheng L, Liu R, Chu C (2015) ACS Comb Sci 17:147

    Article  CAS  PubMed  Google Scholar 

  29. Tang J-L, Ming L, Zhao X-M (2016) J Heterocycl Chem 53:1367

    Article  CAS  Google Scholar 

  30. Zhao F, Tian W-H, Luo F, Cheng H-L, Jiang Y-B, Chen Z (2016) Synth Commun 46:1678

    Article  CAS  Google Scholar 

  31. Voltrová S, Muselli M, Filgas J, Matoušek V, Klepetářová B, Beier P (2017) Org Biomol Chem 15:4962

    Article  PubMed  Google Scholar 

  32. Wu G-L, Wu Q-P (2018) Synthesis 50:2768

    Article  CAS  Google Scholar 

  33. Chinchilla R, Nájera C (2007) Chem Rev 107:874

    Article  CAS  PubMed  Google Scholar 

  34. Gazvoda M, Virant M, Pinter B, Košmrlj J (2018) Nature Comm 9:4814

    Article  CAS  Google Scholar 

  35. Shang H, Hua R, Zheng Q, Zhang J, Liang X, Zhu Q (2010) Appl Organomet Chem 24:473

    CAS  Google Scholar 

  36. Li J, Wang D, Zhang Y, Li J, Chen B (2009) Org Lett 11:3024

    Article  CAS  PubMed  Google Scholar 

  37. Likhar PR, Subhas MS, Roy M, Roy S, Kantam ML (2008) Helv Chim Acta 91:259

    Article  CAS  Google Scholar 

  38. Silva AMS, Vieira JS, Brito CM, Cavaleiro JAS, Patonay T, Lévai A, Elguero J (2004) Monatsh Chem 135:293

    Article  CAS  Google Scholar 

  39. Alonso DA, Nájera C, Pacheco Ma C (2004) J Org Chem 69:1615

    Article  CAS  PubMed  Google Scholar 

  40. Chen L, Li C-J (2004) Org Lett 6:3151

    Article  CAS  PubMed  Google Scholar 

  41. Ryabukhin DS, Sorokoumov VN, Savicheva EA, Boyarskiy VP, Balova IA, Vasilyev AV (2013) Tetrahedron Lett 54:2369

    Article  CAS  Google Scholar 

  42. Majumdar KC, Ray K (2011) Synthesis 23:3767

    Article  CAS  Google Scholar 

  43. Baig RBN, Varma RS (2012) Green Chem 14:625

    Article  CAS  Google Scholar 

  44. Jacob K, Stolle A (2014) Synth Comm 44:1251

    Article  CAS  Google Scholar 

  45. Albuquerque HMT, Santos CMM, Cavaleiro JAS, Silva AMS (2015) Eur J Org Chem 2015:4732

    Article  CAS  Google Scholar 

  46. Bistrović A, Krstulović L, Harej A, Grbčić P, Sedić M, Koštrun S, Pavelić SK, Bajić M, Raić-Malić S (2018) Eur J Med Chem 143:1616

    Article  CAS  PubMed  Google Scholar 

  47. Kappe CO (2008) Chem Soc Rev 37:1127

    Article  CAS  Google Scholar 

  48. Huang K, Yang X (2006) Nat Sci 16:273

    Google Scholar 

  49. Trofimov BA, Volkov PA, Khrapova KO, Telezhkin AA, Inanova NI, Albanov AI, Gusarova NK, Chupakhin ON (2018) Chem Commun 54:3371

    Article  CAS  Google Scholar 

  50. Smit JBM, Marais C, Malan FP, Bezuidenhout BCB (2019) Z Kristallogr NCS 234:359

    CAS  Google Scholar 

  51. Sun W, Wang Y, Wu X, Yao X (2013) Green Chem 15:2356

    Article  CAS  Google Scholar 

  52. Zhang C, Liu J, Xia C (2014) Org Biomol Chem 12:9702

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

Thanks are due to FCT/MEC for the financial support to the QOPNA research Unit (FCT UID/QUI/00062/2013), through national founds and where applicable co-financed by the FEDER, within the PT2020 Partnership Agreement, and to the Portuguese NMR Network. D. H. A. Rocha also thanks FCT for her Ph.D. Grant (SFRH/BD/68991/2010).

Author information

Authors and Affiliations

  1. Department of Chemistry, CICECO-Aveiro Institute of Materials, University of Aveiro, 3810-193, Aveiro, Portugal

    Djenisa H. A. Rocha

  2. Department of Chemistry and QOPNA, University of Aveiro, 3810-193, Aveiro, Portugal

    Djenisa H. A. Rocha, Diana C. G. A. Pinto & Artur M. S. Silva

Authors
  1. Djenisa H. A. Rocha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Diana C. G. A. Pinto
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Artur M. S. Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Djenisa H. A. Rocha.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1078 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rocha, D.H.A., Pinto, D.C.G.A. & Silva, A.M.S. Synthesis of 4,5-disubstituted-1H-1,2,3-triazoles. Monatsh Chem 150, 1479–1486 (2019). https://doi.org/10.1007/s00706-019-02463-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-019-02463-x

Keywords

Search

Navigation