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Catalyst-free grinding method: a new avenue for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and DFT studies on the mechanistic pathway of this category of compounds

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Abstract

A novel, efficient, one-pot, catalyst-free grinding procedure for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile is reported. The condensation of substituted benzaldehydes, 3-amino-5-methylpyrazole, and malononitrile according to a three-component reaction was investigated using density functional theory (DFT) at B3LYP/6-311G level to explore the reaction mechanism. All the routes were studied, the structure of the intermediates was optimized, and all the respective transition states were found. The results of the calculations show that the proposed mechanism relies on four intermediates.

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References

  1. A.M. Li, Y. Ouyang, Z.Y. Wang, Y.Y. Cao, X.Y. Liu, L. Ran, C. Li, L. Li, L. Zhang, K. Qiao, J. Med. Chem. 56, 3593 (2013)

    Article  CAS  PubMed  Google Scholar 

  2. A.H. Shamroukh, A.E. Rashad, H.H. Sayed, J. Phosphorus Sulfur Silicon Rel. Elem. 180, 2347 (2005)

    Article  CAS  Google Scholar 

  3. L. Commeiras, S.C. Woodcock, J.E. Baldwin, R.M. Adlington, A.R. Cowley, P. Wilkinson, Tetrahedron 60, 933 (2004)

    Article  CAS  Google Scholar 

  4. A. Cappelli, C. Nannicini, A. Gallelli, G. Giuliani, S. Valenti, G.P. Mohr, M. Anzini, L. Mennuni, F. Ferrari, G. Caselli, A. Giordani, W. Pereis, F. Makovec, G. Giorgi, S. Vomero, J. Med. Chem. 51, 2137 (2008)

    Article  CAS  PubMed  Google Scholar 

  5. R. Lin, P.J. Connolly, Y. Lu, G. Chin, S. Li, Y. Yu, S. Huang, X. Li, S.L. Emanuel, S.A. Middleton, R.H. Gruninger, M. Adams, A.R. Fuentes-Pesquera, L.M. Greenberger, J. Bioorg. Med. Chem. Lett. 17, 4557 (2007)

    Article  CAS  Google Scholar 

  6. H. de Mello, A. Echevarria, A.M. Bernardino, M. CantoCavalheiro, L.L. Leon, J. Med. Chem. 47, 5427 (2004)

    Article  CAS  PubMed  Google Scholar 

  7. F. Manetti, S. Schenone, F. Bondavalli, C. Brullo, O. Bruno, A. Ranise, L. Mosti, G. Menozzi, P. Fossa, M.L. Trincavelli, C. Martini, A. Martinelli, C. Tintori, M. Botta, J. Med. Chem. 48, 7172 (2005)

    Article  CAS  PubMed  Google Scholar 

  8. B.A. Johns, K.S. Gudmundsson, E.M. Turner, S.H. Allen, V.A. Samano, J.A. Ray, G.A. Freeman, F.L. Boyd, C.J. Sexton, D.W. Selleseth, K.L. Creech, K.R. Moniri, J. Bioorg. Med. Chem. 13, 2397 (2005)

    Article  CAS  Google Scholar 

  9. K.S. Gudmundsson, B.A. Johns, Z. Wang, E.M. Turner, S.H. Allen, G.A. Freeman, F.L.B. Jr, C.J. Sexton, D.W. Selleseth, K.R. Monirib, K.L. Creech, J. Bioorg. Med. Chem. 13, 5346 (2005)

    Article  CAS  Google Scholar 

  10. F.E. Goda, A.A.M. Abdel-Aziz, O.A. Attef, J. Bioorg. Med. Chem. Lett. 12, 1845 (2004)

    Article  CAS  Google Scholar 

  11. N.M. Parekh, K.C. Maheria, J. Res. Chem. Intermed. 38, 885 (2012)

    Article  CAS  Google Scholar 

  12. L. Zare, N.O. Mahmoodi, A. Yahyazadeh, M. Mamaghani, Syn. Commun. 41, 2323 (2011)

    Article  CAS  Google Scholar 

  13. P.A. Wender, J. Nat. Prod. Rep. 31, 433 (2014)

    Article  CAS  Google Scholar 

  14. A.Z. Halimehjani, I.N. Namboothiri, S.E. Hooshmand, RSC Adv. 4, 48022 (2014)

    Article  CAS  Google Scholar 

  15. A.Z. Halimehjani, I.N. Namboothiri, S.E. Hooshmand, RSC Adv. 4, 51794 (2014)

    Article  CAS  Google Scholar 

  16. V. Estévez, M. Villacampa, J.C. Menéndez, J. Chem. Soc. Rev. 43, 4633 (2014)

    Article  Google Scholar 

  17. A. Domling, W. Wang, K. Wang, J. Chem. Rev. 112, 3083 (2012)

    Article  CAS  Google Scholar 

  18. M. Nikpassand, L. Zare Fekri, M. Nabatzadeh, Comb. Chem. High Throughput Screen. 20, 533 (2017)

    Article  CAS  PubMed  Google Scholar 

  19. L. Zare Fekri, M. Nikpassand, J. Chil. Chem. Soc. 57, 1415 (2012)

    Article  Google Scholar 

  20. M. Nikpassand, L. ZareFekri, S. Sanagou, Dyes Pigm. 136, 140 (2017)

    Article  CAS  Google Scholar 

  21. H. Taherkhorsand, M. Nikpassand, Comb. Chem. High Throughput Screen. 21, 65 (2018)

    Article  CAS  PubMed  Google Scholar 

  22. L. Zare Fekri, M. Nikpassand, M. Goldoost, Russ. J. Gen. Chem. 83, 2352 (2013)

    Article  CAS  Google Scholar 

  23. L. Zare Fekri, M. Nikpassand, Russ. J. Gen. Chem. 83, 2395 (2013)

    Article  CAS  Google Scholar 

  24. M. Nikpassand, L. Zare Fekri, K. Hematinezhad, J. Polycycl. Arom. Comp. in press (2018)

  25. M.J. Frisch, et al., GAUSSIAN09, Gaussian, Inc., Revision B. 05, Pittsburgh PA (2009)

  26. J.G. Ma, J.M. Zhang, H.H. Jiang, W.Y. Ma, J.H. Zhou, Chin. Chem. Lett. 19, 375 (2008)

    Article  CAS  Google Scholar 

  27. S. Karmakar, A. Datta, J. Org. Chem. 82, 1558 (2017)

    Article  CAS  PubMed  Google Scholar 

  28. S. Karmakar, A. Datta, J. Phys. Chem. B 121, 7621 (2017)

    Article  CAS  PubMed  Google Scholar 

  29. K. Bhattacharyya, S. Karmakar, A. Datta, Phys. Chem. Chem. Phys. 19, 22482 (2017)

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

Financial support from the Research Council of Islamic Azad University, Rasht Branch is sincerely acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Rasht Branch, Islamic Azad University, Rasht, Iran

    Mohammad Nikpassand & Parissa Naddaf Rahro

  2. Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran

    Leila Zare Fekri

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  1. Mohammad Nikpassand
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  2. Leila Zare Fekri
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  3. Parissa Naddaf Rahro
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Correspondence to Mohammad Nikpassand.

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Nikpassand, M., Fekri, L.Z. & Rahro, P.N. Catalyst-free grinding method: a new avenue for synthesis of 6-amino-3-methyl-4-aryl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile and DFT studies on the mechanistic pathway of this category of compounds. Res Chem Intermed 45, 1707–1719 (2019). https://doi.org/10.1007/s11164-018-3701-9

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