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Synthesis and application of a novel nanomagnetic catalyst with Cl[DABCO-NO2]C(NO2)3 tags in the preparation of pyrazolo[3,4-b]pyridines via anomeric based oxidation

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Abstract

A novel nanomagnetic catalyst with Cl[DABCO-NO2]C(NO2)3 tags was designed, synthesized and fully characterized by several techniques such as Fourier transform infrared spectroscopy, energy-dispersive X-ray spectroscopy, elemental mapping analysis, thermogravimetric analysis, derivative thermal gravimetric, powder X-ray diffraction patterns, field scanning electron microscopy, high resolution transmission electron microscopy, physical adsorption and desorption of N2 isotherms (BET) and vibrating sample magnetometer. The synthesized nanomagnetic particles were used as an efficient and recyclable catalyst for the one-pot three component condensation reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine or 3-methyl-1H-pyrazol-5-amine, aryl aldehydes and malononitrile for the synthesis of pyrazolo[3,4-b]-pyridine derivatives under neat conditions.

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References

  1. O. Deutschmann, H. Knözinger, K. Kochloefl, T. Turek, Heterogeneous Catalysis and Solid Catalysts (Wiley, Weinheim, 2009)

    Book  Google Scholar 

  2. M.A. Zolfigol, T. Azadbakht, V. Khakyzadeh, R. Nejatyami, D. Perrin, RSC Adv. 4, 40036 (2014)

    Article  CAS  Google Scholar 

  3. M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, A. Rostami, A. Zare, N. Iranpoor, M.H. Beyzavi, R. Luque, Green Chem. 15, 2132 (2013)

    Article  CAS  Google Scholar 

  4. H. Sharghi, A. Khoshnood, M.M. Doroodmand, R. Khalifeh, J. Iran. Chem. Soc. 9, 231 (2012)

    Article  CAS  Google Scholar 

  5. H. Sharghi, A. Khoshnood, R. Khalifeh, M.M. Doroodmand, Mol. Divers. 19, 481 (2015)

    Article  CAS  Google Scholar 

  6. S.B. Sapkal, K.F. Shelke, B.B. Shingate, M.S. Shingare, Tetrahedron Lett. 50, 1754 (2009)

    Article  CAS  Google Scholar 

  7. M. Fallah-Mehrjardi, Mini. Rev. Org. Chem. 14, 122 (2017)

    Article  CAS  Google Scholar 

  8. M. Mokhtary, J. Iran. Chem. Soc. 13, 1827 (2016)

    Article  CAS  Google Scholar 

  9. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J.M. Basset, Chem. Rev. 111, 3036 (2011)

    Article  CAS  Google Scholar 

  10. B. Karimi, F. Mansouri, H.M. Mirzaei, ChemCatChem 7, 1736 (2015)

    Article  CAS  Google Scholar 

  11. D. Zhang, C. Zhou, Z. Sun, L.Z. Wu, C.H. Tung, T. Zhang, Nanoscale 4, 6244 (2012)

    Article  CAS  Google Scholar 

  12. M.B. Gawande, P.S. Branco, R.S. Varma, Chem. Soc. Rev. 42, 3371 (2013)

    Article  CAS  Google Scholar 

  13. S. Hu, Y. Guan, Y. Wang, H. Han, Appl. Energ. 88, 2685 (2011)

    Article  CAS  Google Scholar 

  14. A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, J. Afsar, A. Zare, V. Khakyzadeh, M.H. Beyzavi, Chin. J. Catal. 34, 1936 (2013)

    Article  CAS  Google Scholar 

  15. M.A. Zolfigol, M. Yarie, RSC Adv. 5, 103617 (2015)

    Article  CAS  Google Scholar 

  16. H. Sharghi, A. Khoshnood, M.M. Doroodmand, R. Khalifeh, J. Heterocycl. Chem. 53, 164 (2016)

    Article  CAS  Google Scholar 

  17. E. Juaristi, G. Cuevas, Tetrahedron 48, 5019 (1992)

    Article  CAS  Google Scholar 

  18. S.A. Glover, Tetrahedron 54, 7229 (1998)

    Article  CAS  Google Scholar 

  19. E. Juaristi, Y. Bandala, Adv. Heterocycl. Chem. 105, 189 (2012)

    Article  CAS  Google Scholar 

  20. C.M. Filloux, Angew. Chem. Int. Ed. 54, 8880 (2015)

    Article  CAS  Google Scholar 

  21. M. Yarie, Iran. J. Catal. 7, 85 (2017)

    CAS  Google Scholar 

  22. G. Hamasaka, H. Tsuji, Y. Uozumi, Synlett 26, 2037 (2015)

    Article  CAS  Google Scholar 

  23. T. He, R. Shi, Y. Gong, G. Jiang, M. Liu, S. Qian, Z. Wang, Synlett 27, 1864 (2016)

    Article  CAS  Google Scholar 

  24. C.-B. Bai, N.-X. Wang, Y. Xing, X.-W. Lan, Synlett 28, 402 (2017)

    CAS  Google Scholar 

  25. N.-X. Wang, J. Zhao, Synlett 18, 2785 (2007)

    Article  Google Scholar 

  26. L.F. Pedrosa, W.P. de Macedo, A.C.R. Furtado, G.P. Guedes, J.C. Borges, J.A.L.C. Resende, M.G.F. Vaz, A.M.R. Bernardino, M.C. de Souza, ARKIVOC iv, 38 (2014)

    Google Scholar 

  27. V. Kumar, K. Kaur, G.K. Gupta, A.K. Sharma, Eur. J. Med. Chem. 69, 735 (2013)

    Article  CAS  Google Scholar 

  28. D.-Q. Shi, H. Yao, J.-W. Shi, Synth. Commun. 38, 1662 (2008)

    Article  CAS  Google Scholar 

  29. I.H. Eissa, A.M. El-Naggar, M.A. El-Hashash, Bioorg. Chem. 67, 43 (2016)

    Article  CAS  Google Scholar 

  30. T.I. El-Emary, J. Chin. Chem. Soc. 54, 507 (2007)

    Article  CAS  Google Scholar 

  31. X. Zhang, X. Li, X. Fan, X. Wang, J. Wang, G. Qu, Aust. J. Chem. 62, 382 (2009)

    Article  CAS  Google Scholar 

  32. Y.L. Chen, Chem. Abstr. 124, 232447 (1995)

    Google Scholar 

  33. J. Quiroga, S. Cruz, B. Insuasty, R. Abonia, J. Heterocycl. Chem. 38, 53 (2001)

    Article  CAS  Google Scholar 

  34. B. Zhao, Y. Li, P. Xu, Y. Dai, C. Luo, Y. Sun, J. Ai, M. Geng, W. Duan, ACS Med. Chem. Lett. 7, 629 (2016)

    Article  CAS  Google Scholar 

  35. M.D. Hill, H. Fang, J.M. Brown, T. Molski, A. Easton, X. Han, R. Miller, M. Hill-Drzewi, L. Gallagher, M. Matchett, M. Gulianello, A. Balakrishnan, R.L. Bertekap, K.S. Santone, V.J. Whiterock, X. Zhuo, J.J. Bronson, J.E. Macor, A.P. Degnan, ACS Med. Chem. Lett. 7, 1082 (2016)

    Article  CAS  Google Scholar 

  36. M.A. Zolfigol, A. Khazaei, S. Alaie, S. Baghery, F. Maleki, Y. Bayat, A. Asghari, RSC Adv. 6, 58667 (2016)

    Article  CAS  Google Scholar 

  37. M.A. Zolfigol, H. Gholami, V. Khakyzadeh, Principles of Organic Synthesis with a New Approach, 3rd edn. (Bu-Ali Sina University Publishers, Hamedan, 2014), p. 26

    Google Scholar 

  38. S.J. Angyal, K. James, Aust. J. Chem. 23, 1209 (1970)

    Article  CAS  Google Scholar 

  39. J.M. Erhardt, J.D. Wuest, J. Am. Chem. Soc. 102, 6363 (1980)

    Article  CAS  Google Scholar 

  40. T.J. Atkins, J. Am. Chem. Soc. 102, 6364 (1980)

    Article  CAS  Google Scholar 

  41. J.M. Erhardt, E.R. Grover, J.D. Wuest, J. Am. Chem. Soc. 102, 6365 (1980)

    Article  CAS  Google Scholar 

  42. M.A. Zolfigol, F. Afsharnadery, S. Baghery, S. Salehzadeh, F. Maleki, RSC Adv. 5, 75555 (2015)

    Article  CAS  Google Scholar 

  43. M.A. Zolfigol, M. Safaiee, F. Afsharnadery, N. Bahrami-Nejad, S. Baghery, S. Salehzadeh, F. Maleki, RSC Adv. 5, 100546 (2015)

    Article  CAS  Google Scholar 

  44. A.R. Moosavi-Zare, M.A. Zolfigol, Z. Rezanejad, Can. J. Chem. 94, 626 (2016)

    Article  CAS  Google Scholar 

  45. M.A. Zolfigol, M. Kiafar, M. Yarie, A. Taherpour, M. Saeidi-Rad, RSC Adv. 6, 50100 (2016)

    Article  CAS  Google Scholar 

  46. M.A. Zolfigol, M. Yarie, Appl. Organometal. Chem. 31, 3598 (2017)

    Article  Google Scholar 

  47. M.A. Zolfigol, M. Kiafar, M. Yarie, A. Taherpour, T. Fellowes, A.N. Hancok, A. Yari, J. Mol. Struct. 1137, 674 (2017)

    Article  CAS  Google Scholar 

  48. M. Kiafar, M.A. Zolfigol, M. Yarie, A. Taherpour, RSC Adv. 6, 102280 (2016)

    Article  CAS  Google Scholar 

  49. M.A. Zolfigol, M. Safaiee, B. Ebrahimghasri, S. Baghery, S. Alaie, M. Kiafar, A. Taherpour, Y. Bayat, A. Asgari, J. Iran. Chem. Soc. 14, 1839 (2017)

    Article  CAS  Google Scholar 

  50. S. Baghery, M.A. Zolfigol, F. Maleki, New J. Chem. 41, 9276 (2017)

    Article  CAS  Google Scholar 

  51. N. Koukabi, E. Kolvari, A. Khazaei, M.A. Zolfigol, B.S. Shaghasemi, H.R. Khavasi, Chem. Commun. 47, 9230 (2011)

    Article  CAS  Google Scholar 

  52. N. Koukabi, E. Kolvari, M.A. Zolfigol, A. Khazaei, B.S. Shaghasemi, B. Fasahati, Adv. Synth. Catal. 354, 2001 (2012)

    Article  CAS  Google Scholar 

  53. T. Azadbakht, M.A. Zolfigol, R. Azadbakht, V. Khakizadeh, D. Perrin, New J. Chem. 39, 439 (2015)

    Article  CAS  Google Scholar 

  54. M. Safaiee, M.A. Zolfigol, F. Afsharnadery, S. Baghery, RSC Adv. 5, 102340 (2015)

    Article  CAS  Google Scholar 

  55. M. Yarie, M.A. Zolfigol, Y. Bayat, A. Asgari, D.A. Alonso, A. Khoshnood, RSC Adv. 6, 82842 (2016)

    Article  CAS  Google Scholar 

  56. L. Mohammadi, M.A. Zolfigol, M. Ebrahiminia, K.P. Roberts, S. Ansari, T. Azadbakht, S.R. Hussaini, Catal. Commun. 102, 44 (2017)

    Article  CAS  Google Scholar 

  57. M. Rajabi-Salek, M.A. Zolfigol, M. Zarei, Res. Chem. Intermed (2018)

  58. S. Moradi, M.A. Zolfigol, M. Zarei, D.A. Alonso, A. Khoshnood, A. Tajally, Appl. Organomet. Chem. (2018).

  59. M.A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, V. Khakyzadeh, S. Azizian, J. Mol. Catal. A Chem. 418–419, 54 (2016)

    Article  Google Scholar 

  60. M.A. Zolfigol, A.R. Moosavi-Zare, M. Zarei, A. Zare, E. Noroozizadeh, R. Karamian, M. Asadbegy, RSC Adv. 6, 62460 (2016)

    Article  CAS  Google Scholar 

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Acknowledgements

We thank Bu-Ali Sina University, Iran National Science Foundation (INSF) (Grant Number: 95831207), National Elites Foundation, University of Alicante (VIGROB-173, UAUSTI16-03), and the Spanish Ministerio de Economía y Competitividad (CTQ2015-66624-P) for financial support to our research groups.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Javad Afsar, Mohammad Ali Zolfigol & Ardeshir Khazaei

  2. Organic Chemistry Department, Organic Synthesis Institute, Alicante University, Apdo. 99, 03080, Alicante, Spain

    Diego A. Alonso & Abbas Khoshnood

  3. Faculty of Chemistry and Chemical Engineering, Malek Ashtar University of Technology, Tehran, Iran

    Yadollah Bayat & Asiye Asgari

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  1. Javad Afsar
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Correspondence to Mohammad Ali Zolfigol.

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Afsar, J., Zolfigol, M.A., Khazaei, A. et al. Synthesis and application of a novel nanomagnetic catalyst with Cl[DABCO-NO2]C(NO2)3 tags in the preparation of pyrazolo[3,4-b]pyridines via anomeric based oxidation. Res Chem Intermed 44, 7595–7618 (2018). https://doi.org/10.1007/s11164-018-3576-9

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