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One-pot three-component synthesis of a series of 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles in the presence of aluminum oxide as a nanocatalyst

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Chemistry of Heterocyclic Compounds Aims and scope

One-pot three-component reaction of arylglyoxals, 3-aryl-3-oxopropanenitriles, and 5-amino-1-aryl-3-methylpyrazoles using various solvent systems and different catalysts under reflux conditions afforded the corresponding 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]- pyridine-5-carbonitrile derivatives. The best yields (70–91%) were obtained using Al2O3 as a nanocatalyst in H2O–EtOH, 1:1, under reflux conditions. The simplicity of workup procedure, the novelty of pyrazolopyridines, green solvent system, easy preparation of a nanocatalyst, and good to excellent yields of the products are the advantages of this synthetic strategy. The structures of all products were confirmed by FT-IR, 1H and13C NMR, and mass spectral data.

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The authors are grateful for support from the Urmia University.

We also thank Prof. R. H. Prager from the Flinders University of Australia for proof-reading and language editing of this article.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Urmia University, P. O. Box 57153-165, Urmia, Iran

    Fatemeh Majidi Arlan & Jabbar Khalafy

  2. Research Department of Analytical Chemistry, Iranian Academic Center for Education, Culture and Research, P. O. Box 57155-397, Urmia, Iran

    Ramin Maleki

Authors
  1. Fatemeh Majidi Arlan
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  2. Jabbar Khalafy
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Correspondence to Fatemeh Majidi Arlan.

Additional information

Supplementary information file containing 1H NMR spectra of compounds 4a–p and mass spectrum of compound is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(1), 51–57

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Arlan, F.M., Khalafy, J. & Maleki, R. One-pot three-component synthesis of a series of 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles in the presence of aluminum oxide as a nanocatalyst. Chem Heterocycl Comp 54, 51–57 (2018). https://doi.org/10.1007/s10593-018-2229-7

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