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Highly regioselective one-step synthesis of 1-benzyl-5-formyl-1,2,3-triazole-4-carboxylates

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A novel methodology has been developed to afford 1,4,5-trisubstituted 1-benzyl-5-formyl-1,2,3-triazole-4-carboxylates in one step under mild conditions. This method includes the reduction of the ester functional group to an aldehyde using lithium tri-tert-butoxyaluminum hydride. Especially, this method offers a different perspective for fully substituted 1,2,3-triazoles with high regioselectivity and high yields. The structure of fully substituted triazoles was verified using FTIR, 1H, 13C NMR spectroscopy, HRMS, advanced NMR techniques (COSY, C-APT, HSQC, and HMBC), and X-ray crystallography.

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References

  1. Buckle, D. R.; Rockell, C. J. M; Smith, H.; Spicer, B. A. J. Med. Chem. 1986, 29, 2262.

    Article  CAS  PubMed  Google Scholar 

  2. Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905.

    Article  CAS  PubMed  Google Scholar 

  3. Lauria, A.; Delisi, R.; Mingoia, F.; Terenzi, A.; Martorana, A.; Barone, G.; Almerico, A. M. Eur. J. Org. Chem. 2014, 3289.

  4. Nguyen, D. T.; Ngo, T. H.; Tran, H. T.; Dinh, T. P.; Do, P. T.; Nguyen, H. B.; Tran, L. T. P.; Ta, H. M. Chem. Heterocycl. Compd. 2021, 57, 1037.

    Article  CAS  Google Scholar 

  5. Bozorov, K.; Zhao, J.; Aisa, H. A. Bioorg. Med. Chem. 2019, 27, 3511.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Tapkir, S. R.; Patil, R. H.; Galave, S. A.; Phadtare, G. R.; Khedkar, V. M.; Garud, D. R. J. Heterocycl. Chem. 2022, 59, 739.

    Article  CAS  Google Scholar 

  7. Oubella, A.; Bimoussa, A.; Byadi, S.; Fawzi, M.; Laamari, Y.; Auhmani, A.; Morjani, H.; Robert, A.; Riahi, A.; Itto, M. Y. A. J. Mol. Struct. 2022, 1265, 133383.

    Article  CAS  Google Scholar 

  8. Huisgen, R. Angew. Chem., Int. Ed. 1963, 2, 565.

  9. Dheer, D.; Singh, V.; Shankar, R. Bioorg. Chem. 2017, 71, 30.

    Article  CAS  PubMed  Google Scholar 

  10. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.

  11. Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923.

    Article  CAS  PubMed  Google Scholar 

  12. Li, L.; Shang, T.; Ma, X.; Guo, H.; Zhu, A.; Zhang, G. Synlett 2015, 26, 695.

    Article  CAS  Google Scholar 

  13. Chuprakov, S.; Chernyak, N.; Dudnik A. S.; Gevorgyan, V. Org. Lett. 2007, 9, 2333.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  14. Shiri, P.; Amani, A. M.; Mayer-Gall, T. Beilstein J. Org. Chem. 2021, 17, 1600.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. Ramanaiah, K. C. V.; Stevens, E. D.; Trudell, M. L.; Pagoria, P. F. J. Heterocycl. Chem. 2000, 37, 1597.

    Article  CAS  Google Scholar 

  16. Pokhodylo, N. T.; Shyyka, O. Ya.; Obushak, M. D. Chem. Heterocycl. Compd. 2018, 54, 773.

  17. Fariña, F.; Fernández, P.; Fraile, M. T.; Martín, M. V.; Martín, M. R. Heterocycles 1989, 29, 967.

    Article  Google Scholar 

  18. Baykal, A.; Zhang, D.; Knelles, J.; Alt, I. T.; Plietker, B. Asian J. Chem. 2019, 14, 3003.

    Article  CAS  Google Scholar 

  19. Jomova, K.; Valko, M. Toxicology 2011, 283, 65.

    Article  CAS  PubMed  Google Scholar 

  20. Gierlich, J.; Burley, G. A.; Gramlich, P. M. E.; Hammond, D. M.; Carell, T. Org. Lett. 2006, 8, 3639.

    Article  CAS  PubMed  Google Scholar 

  21. Kennedy, D. C.; McKay, C. S.; Legault, M. C. B.; Danielson, D. C.; Blake, J. A.; Pegoraro, A. F.; Stolow, A.; Mester, Z.; Pezacki, J. P. J. Am. Chem. Soc. 2011, 133, 17993.

    Article  CAS  PubMed  Google Scholar 

  22. Zheng, H.; McDonald, R.; Hall, D. G. Chem.–Eur. J. 2010, 16, 5454.

  23. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry: Part B: Reaction and Synthesis; Springer, 2007.

  24. Pérez-Serrano, L.; Casarrubios, L.; Dominguez, G.; González-Pérez, P.; Pérez-Castells, J. Synthesis 2002, 1810.

  25. Dransfield, P. J.; Dilley, A. S.; Wang, S.; Romo, D. Tetrahedron 2006, 62, 5223.

    Article  CAS  Google Scholar 

  26. Devine, W. G.; Diaz-Gonzalez, R.; Ceballos-Perez, G.; Rojas, D.; Satoh, T.; Tear, W.; Ranade, R. M.; Barros-Álvarez, X.; Hol, W. G. J.; Buckner, F. S.; Navarro, M.; Pollastri, M. P. ACS Infect. Dis. 2017, 3, 225.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. Lopchuk, J. M.; Gribble, G. W. Heterocycles 2011, 82, 1617.

    CAS  Google Scholar 

  28. Deng, Y.; Liang, X.; Wei, K.; Yang, Y. R. J. Am. Chem. Soc. 2021, 143, 20622.

    Article  CAS  PubMed  Google Scholar 

  29. Yoshida, K.; Hayashi, K.; Yanagisawa, A. Org. Lett. 2011, 13, 4762.

    Article  CAS  PubMed  Google Scholar 

  30. Yasui, E.; Tsuda, J.; Ohnuki, S.; Nugumo, S. Chem. Pharm. Bull. 2016, 64, 1262.

    Article  CAS  Google Scholar 

  31. Shanmugavelan, P.; Nagarajan, S.; Sathishkumar, M.; Ponnuswamy, A.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2011, 21, 7273.

    Article  CAS  PubMed  Google Scholar 

  32. Shaikh, M. H.; Subhedar, D. D.; Arkile, M.; Khedkar, V. M.; Jadhav, N.; Sarkar, D.; Shingate, B. B. Bioorg. Med. Chem. Lett. 2016, 26, 561.

    Article  CAS  PubMed  Google Scholar 

  33. Sri Ramya, P. V.; Angapelly, S.; Guntuku, L.; Digwal, C. S.; Babu, B. N.; Naidu, V. G. M.; Kamal, A. Eur. J. Med. Chem. 2017, 127, 100.

    Article  CAS  PubMed  Google Scholar 

  34. Rodríguez-Hernández, D.; Demuner, A. J.; Barbosa, L. C. A.; Heller, L.; Csuk, R. Eur. J. Med. Chem. 2016, 115, 257.

    Article  PubMed  Google Scholar 

  35. Biagi, G.; Giorgi, I.; Livi, O.; Manera, C.; Scartoni, V.; Betti, L.; Giannaccini, G.; Lucacchini, A. Farmaco 1999, 54, 615.

    Article  CAS  Google Scholar 

  36. Abu-Orabi, S. T.; Atfah, A. M.; Jibril, I.; Mari'i, F. M.; Ali, A. A. J. Heterocycl. Chem. 1989, 26, 1461.

    Article  CAS  Google Scholar 

  37. Barman, M. K.; Sinha, A. K.; Nembenna, S. Green Chem. 2016, 18, 2534.

    Article  CAS  Google Scholar 

  38. Tarawneh, A. H.; Al-Momani, L. A.; León, F.; Jain, S. K.; Gadetskaya, V. A.; Abu-Orabi, S. T.; Tekwani, B. L.; Cutler, S. J. Med. Chem. Res. 2018, 27, 1269.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  39. Butler, C. R.; Bendesky, J.; Schoffstall, A. M. Molecules 2012, 26, 5589.

    Article  Google Scholar 

  40. SAINT, version 8.34A; Bruker AXS, Inc.: Madison, 2013.

  41. SADABS, version 2014/5; Bruker AXS, Inc.: Madison, 2014.

  42. APEX2, version 2014.11–0; Bruker AXS, Inc.: Madison, 2014.

  43. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, 71, 3.

  44. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

  45. Spek, A. L. Acta Crystallogr., Sect. D: Biol. Crystallogr. 2009, 65, 148.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Gazi University, Ankara, 06560, Turkey

    Guler Yagiz Erdemir & Aliye Altundas

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  1. Guler Yagiz Erdemir
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  2. Aliye Altundas
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Correspondence to Aliye Altundas.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(4/5), 267–276

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Erdemir, G.Y., Altundas, A. Highly regioselective one-step synthesis of 1-benzyl-5-formyl-1,2,3-triazole-4-carboxylates. Chem Heterocycl Comp 59, 267–276 (2023). https://doi.org/10.1007/s10593-023-03192-0

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