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

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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Acknowledgements

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

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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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Keywords

  • Grinding reaction
  • DFT
  • Mechanism
  • Intermediate
  • Transition state