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Synthesis of 1,4-disubstituted-1,2,3-triazoles using starch-functionalized copper (II) acetate as a recyclable heterogeneous catalyst in water

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Abstract

Copper (II) acetate is covalently anchored onto the surface of chemically modified starch and the resultant heterogeneous catalyst was investigated for the regioselective synthesis of 1,4-disubstituted-1,2,3-triazoles via Huisgen 1,3-dipolar cycloaddition reaction between terminal alkynes, benzyl/allyl/alkyl halides and NaN3 in distilled water at room temperature. Further, starch functionalized copper (II) acetate could be recovered by simple filtration and recycled up to several consecutive runs without loss of significant activity. The catalyst is characterized by FTIR, thermal analysis, XRD, SEM, TEM, and AAS.

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References

  1. W. Q. Fan and A. R. Katritzky, 1,2,3 Triazoles. In Comprehensive heterocycle chemistry II; A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Eds.; Pergamon Press: New York, NY, USA, 4, 1, (1996)

  2. A.R. Katritzky, Y. Zhang, S.K. Singh, Heterocycles 60, 1225 (2003)

    Article  CAS  Google Scholar 

  3. A.G. Nasibulin, E.I. Kauppinen, D.P. Brown, J.K. Jokiniemi, J. Phys. Chem. B 105, 11067 (2001)

    Article  CAS  Google Scholar 

  4. R. Alvarez, S. Velazquez, R. San, S. Aquaro, C.E. De, C.F. Perno, A. Karlsson, J. Balzarini, M.J. Camarasa, J. Med. Chem. 37, 4185 (1994)

    Article  CAS  PubMed  Google Scholar 

  5. S. Velazquez, R. Alvarez, C. Perez, F. Gago, C.E. De, J. Balzarini, J.M. Camarasa, Antiviral Chem. Chemother. 9, 481 (1998)

    Article  CAS  Google Scholar 

  6. M. Whiting, J. Muldoon, Y.C. Lin, S.M. Silverman, W. Lindstrom, A.J. Olson, H.C. Kolb, M.G. Finn, B.K. Sharpless, J.H. Elder, V.V. Fokin, Angew. Chem. Int. Ed. 45, 1435 (2006)

    Article  CAS  Google Scholar 

  7. A. Brik, J. Muldoon, Y.C. Lin, J.H. Elder, D.S. Goodsell, A.J. Olson, V.V. Fokin, K.B. Sharpless, C.H. Wong, Chem. Bio. Chem. 4, 1246 (2003)

    Article  CAS  PubMed  Google Scholar 

  8. M.J. Genin, D.A. Allwine, D.J. Anderson, M.R. Barbachyn, D.M. Emmert, S.A. Garmon, D.R. Graber, K.C. Grega, J.B. Hester, D.K. Hutchinson, J. Morris, R.J. Reischer, C.W. Ford, G.E. Zurenko, J.C. Hamel, R.D. Schaadt, D. Stapert, B.H. Yagi, J. Med. Chem. 43, 953 (2000)

    Article  CAS  PubMed  Google Scholar 

  9. L.L. Brockunier, E.R. Parmee, H.O. Ok, M.R. Candelore, M.A. Cascieri, L.F. Colwell, L. Deng, W.P. Feeney, M.J. Forrest, G.J. Hom, D.E. MacIntyre, L. Tota, M.J. Wyvratt, M.H. Fisher, A.E. Weber, Bioorg. Med. Chem. Lett. 10, 2111 (2000)

    Article  CAS  PubMed  Google Scholar 

  10. V. Pande, M.J. Ramos, Bioorg. Med. Chem. Lett. 15, 5129 (2005)

    Article  CAS  PubMed  Google Scholar 

  11. P.H. Olesen, A.R. Sorensen, B. Urso, P. Kurtzhals, A.N. Bowler, U. Ehrbar, B.F. Hansen, J. Med. Chem. 46, 3333 (2003)

    Article  CAS  PubMed  Google Scholar 

  12. A. Krasinski, Z. Radic, R. Manetsch, J. Raushel, P. Taylor, B.K. Sharpless, H.C. Kolb, J. Am. Chem. Soc. 127, 6686 (2005)

    Article  CAS  PubMed  Google Scholar 

  13. V.P. Mocharla, B. Colasson, L.V. Lee, S. Roeper, B.K. Sharpless, C.H. Wong, H.C. Kolb, Angew. Chem. Int. Ed. 1, 116 (2005)

    Article  Google Scholar 

  14. R.G. Micetich, S.N. Maiti, P. Spevak, T.W. Hall, S. Yamabe, N. Ishida, M. Tanaka, T. Yamazaki, A. Nakai, K. Ogawa, J. Med. Chem. 30, 1469 (1987)

    Article  CAS  PubMed  Google Scholar 

  15. P. Actor, J.V. Uri, L. Phillips, C.S. Sachs, J.R.G. Zajac, D.A. Berges, G.L. Dunn, J.R.E. Hoover, J.A. Weisbach, J. Antibiot. 28, 594 (1975)

    Article  CAS  Google Scholar 

  16. H.C. Kolb, K.B. Sharpless, Drug Discov Today 8, 1128 (2003)

    Article  CAS  PubMed  Google Scholar 

  17. R.K. O’Reilly, M.J. Joralemon, K.L. Wooley, C.J. Hawker, Chem. Mater. 17, 5976 (2005)

    Article  Google Scholar 

  18. D.A. Fleming, C.J. Thode, M.E. Williams, Chem. Mater. 18, 2327 (2006)

    Article  CAS  Google Scholar 

  19. J.P. Collman, N.K. Devaraj, T.P.A. Eberspacher, C.E.D. Chidsey, Langmuir 22, 2457 (2006)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  20. R. Huisgen, Proc. Chem. Soc. 357 (1961)

  21. H.C. Kolb, M.G. Finn, K.B. Sharpless, Angew. Chem. Int. Ed. 40, 2004 (2001)

    Article  CAS  Google Scholar 

  22. J. Barluenga, C. Valdes, G. Beltran, M. Escribano, F. Aznar, Angew. Chem. Int. Ed. 45, 6893 (2006)

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  24. D. Wang, N. Li, M. Zhao, W. Shi, C. Ma, B. Chen, Green Chem. 12, 2120 (2010)

    Article  CAS  Google Scholar 

  25. M. Liu, O. Reiser, Org. Lett. 13, 1102 (2011)

    Article  CAS  PubMed  Google Scholar 

  26. J. Albadia, J. A. Shiranb, A. Mansournezhad, J. Chem. Sci. 147 (2014)

  27. B.S.P.A. Kumar, K.H.V. Reddy, B. Madhav, K. Ramesh, Y.V.D. Nageswar, Tetrahedron Lett. 53, 4595 (2012)

    Article  Google Scholar 

  28. R.B.N. Baig, R.S. Varma, Green Chem. 15, 1839 (2013)

    Article  CAS  Google Scholar 

  29. N. Aflak, H.B.E. Ayouchia, L. Bahsis, H. Anane, R. Laamari, A. Pascual-Alvarez, D. Armentano, S.-E. Stirib, Polyhedron 170, 630 (2019)

    Article  CAS  Google Scholar 

  30. J.-C. Castillo, N.-F. Bravo, L.-V. Tamayo, P.-D. Mestizo, J. Hurtado, M. Macias, J. Portilla, ACS Omega 5, 30148 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  31. H. Lee, J.K. Lee, S.-J. Min, H. Seo, Y. Lee, H. Rhee, J. Org. Chem. 83, 4805 (2018)

    Article  CAS  PubMed  Google Scholar 

  32. M. Rajabi, J. Albadi, A. Momeni, Res. Chem. Intermed. 46, 3879 (2020)

    Article  CAS  Google Scholar 

  33. A.G. Samuel, B. Jebasingh, ChemistrySelect 5, 645 (2020)

    Article  Google Scholar 

  34. A. Khoshnoud, A. Pourali, Org. Prep. Proced. Int. 53, 1 (2021)

    Article  Google Scholar 

  35. P. Saini, G. Singh, G. Kaur, J. Singh, H. Singh, Mol. Catal. 504, 111432 (2021)

    Article  CAS  Google Scholar 

  36. X. Chen, W. Yao, F. Gao, D. Zheng, Q. Wang, J. Cao, H. Tan, Y. Zhang, J. Renew. Mater. 9, 979 (2021)

    Article  CAS  Google Scholar 

  37. P. Kumar, P. Gupta, C. Sharma, Catal. Sci. Technol. 11, 3775 (2021)

    Article  CAS  Google Scholar 

  38. P. Gupta, N. Prakash, Y. Ramawat, P. Rajput, A. Fayaz, T.K. Roy, Lett. Org. Chem. 19, 19 (2022)

    Article  Google Scholar 

  39. A. Mahajan, P. Gupta, New J. Chem. 44, 12897 (2020)

    Article  CAS  Google Scholar 

  40. A. Mahajan, P. Gupta, Environ. Chem. Lett. 18, 299 (2020)

    Article  CAS  Google Scholar 

  41. Z. Gonda, Z. Novak, Dalton Trans. 39, 726 (2010)

    Article  CAS  PubMed  Google Scholar 

  42. S. Kale, S. Kahandal, S. Disale, R. Jayaram, Current. Chem. Lett. 1, 69 (2012)

    CAS  Google Scholar 

  43. T. Miao, L. Wang, Synthesis 363 (2008)

  44. K. Kacprzak, Synlett 5, 943 (2005)

    Article  Google Scholar 

  45. C. Girard, E. Onen, M. Aufort, S. Beauviere, E. Samson, J. Herscovici, Org. Lett. 8, 1689 (2006)

    Article  CAS  PubMed  Google Scholar 

  46. A.N. Prasad, B.M. Reddy, E.-Y. Jeong, S.-E. Park, RSC Adv. 4, 29772 (2014)

    Article  CAS  Google Scholar 

  47. F. Rezaei, M.A. Amrollahi, R. Khalifeh, Inorg. Chim. Acta 489, 8 (2019)

    Article  CAS  Google Scholar 

  48. A. Kumar, S. Verma, D.D. Pathak, J. Environ. Chem. Eng. 9, 105791 (2021)

    Article  CAS  Google Scholar 

  49. A. Nunes, L. Djakovitch, L. Khrouz, F.-X. Felpin, V. Dufaud, J. Mol. Catal. A Chem. 437, 15 (2017)

    Google Scholar 

  50. Y. Zhang, Z. Zhang, Y. Chen, Y. Li, Res. Chem. Intermed. 43, 7307 (2017)

    Article  CAS  Google Scholar 

  51. F.M. Mogaddam, M. Eslami, S.E. Ayati, ChemistrySelect 2, 11942 (2017)

    Article  CAS  Google Scholar 

  52. A. Khoshnoud, A.R. Pourali, Org. Prep. Proced. Int. 53, 509 (2021)

    Article  CAS  Google Scholar 

  53. A.K. Sardarian, F. Mohammadi, M. Esmaeilpour, Res. Chem. Intermed. 45, 1437–1456 (2019)

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Acknowledgements

We are grateful to SAIF, Punjab University, Chandigarh, for XRD, SEM and TEM; Head, Institute Instrumentation Centre, Indian Institute of Technology, Roorkee for TGA; and SAIF, Nagpur University, Nagpur, for AAS analysis.

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Dr. Princy prepared the manuscript and Dr. Tahira performed the experiments in lab. Pawan Kumar and Bindu Syal revised/modified the manuscript, performed the repeated experiments in the lab as per the directions of Editor/reviewers.

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Correspondence to Tahira Shamim.

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Gupta, P., Kumar, P., Syal, B. et al. Synthesis of 1,4-disubstituted-1,2,3-triazoles using starch-functionalized copper (II) acetate as a recyclable heterogeneous catalyst in water. Res Chem Intermed 48, 4601–4615 (2022). https://doi.org/10.1007/s11164-022-04829-z

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