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Synthetic utility of a heterocyclic o-aminoaldehyde: synthesis of pyrazolopyridopyrimidines, pyrazolonaphthyridines, and pyrazolopyrimidonaphthyridinones

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Abstract

A series of various polysubstituted pyrazolo[3,4-h][1,6]naphthyridines, benzo[b]pyrazolo[3,4-h][1,6]naphthyridines, and pyrazolo[4′,3′:5,6]pyrido[4,3-d]pyrimidines were synthesized by Friedländer condensation of 4-amino-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde (o-aminoaldehyde) with active methylene compounds. The o-aminoaldehyde was functionalized to o-aminonitrile and o-aminocarboxamide with malononitrile and cyanoacetamide, respectively, which on condensation with monosubstituted ureas and acetic anhydride, respectively, afforded pyrazolo[3,4-h]pyrimido[4,5-b][1,6]naphthyridines.

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Acknowledgments

The authors are thankful to UGC, New Delhi, for the financial assistance under the Major Research Project. We also thank authorities of NDMVP Samaj’s and KTHM College, Nashik for facilities.

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Authors and Affiliations

  1. Department of Chemistry, Organic Chemistry Research Centre, K. T. H. M. College, Gangapur Road, Nashik, Maharashtra, 422002, India

    Sandeep M. Bagul, Dilip R. Birari , Maruti G. Ghagare, Raghunath B. Toche & Madhukar N. Jachak

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  1. Sandeep M. Bagul
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  2. Dilip R. Birari
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  3. Maruti G. Ghagare
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  4. Raghunath B. Toche
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  5. Madhukar N. Jachak
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Correspondence to Madhukar N. Jachak.

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Bagul, S.M., Birari , D.R., Ghagare, M.G. et al. Synthetic utility of a heterocyclic o-aminoaldehyde: synthesis of pyrazolopyridopyrimidines, pyrazolonaphthyridines, and pyrazolopyrimidonaphthyridinones. Monatsh Chem 142, 169–175 (2011). https://doi.org/10.1007/s00706-010-0443-9

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  • DOI: https://doi.org/10.1007/s00706-010-0443-9

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