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Synthesis of 3-aminopyrazolo[3,4-b]pyridine-4-carbonitriles

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Abstract

Annulation of 2-chloropyridine-3,4-dicarbonitriles with hydrazine hydrate and N,N-dimethylhydrazine afforded 3-aminopyrazolo[3,4-b]pyridine-4-carbonitriles and 3-amino-1-methylpyrazolo[3,4-b]pyridine- 4-carbonitriles, respectively.

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References

  1. Chavva, K., Pillalamarri, S., Banda, V., Gautham, S., Gaddamedi, J., Yedla, P., Kumar, C.G., and Banda, N., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 5893.

    Article  CAS  Google Scholar 

  2. Huart, A.-S., Saxty, B., Merritt, A., Nekulova, M., Lewis, S., Huang, Y., Vojtesek, B., Kettleborough, C., and Hupp, T.R., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 5578.

    Article  CAS  Google Scholar 

  3. Kurumurthy, C., Veeraswamy, B., Rao, P.S., Kumar, G.S., Rao, P.S., Reddy, V.L., Rao, J.V., and Narsaiah, B., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 746.

    Article  CAS  Google Scholar 

  4. Dai, Y., Hartandi, K., Soni, N.B., Pease, L.J., Reuter, D.R., Olson, A.M., Osterling, D.J., Doktor, S.Z., Albert, D.H., Bouska, J.J., Glaser, K.B., Marcotte, P.A., Stewart, K.D., Davidsen, S.K., and Michaelides, M.R., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 386.

    Article  CAS  Google Scholar 

  5. Orlikova, B., Chaouni, W., Schumacher, M., Aadil, M., Diederich, M., and Kirsch, G., Eur. J. Med. Chem., 2014, vol. 85, p. 450.

    Article  CAS  Google Scholar 

  6. Van Linden, O.P.J., Farenc, C., Zoutman, W.H., Hameetman, L., Wijtmans, M., Leurs, R., Tensen, C.P., Siegal, G., and de Esch, I.J.P., Eur. J. Med. Chem., 2012, vol. 47, p. 493.

    Article  Google Scholar 

  7. Bekhit, A.A., El-Sayed, O.A., Aboul-Enein, H.Y., Siddiqui, Y.M., and Al-Ahdal, M.N., Arch. Pharm., 2005, vol. 338, p. 74.

    Article  CAS  Google Scholar 

  8. Farag, A., El-Essawy, D.A., and El-Etrawy, A.-A.Sh., J. Heterocycl. Chem., 2014, vol. 51, p. 191.

    Article  Google Scholar 

  9. Foks, H., Pancechowska-Ksepko, D., Kedzia, A., Zwolska, Z., Janowiec, M., and Augustynowicz-Kopec, E., Farmaco, 2015, vol. 60, p. 513.

    Article  Google Scholar 

  10. Gouda, M.A., Arch. Pharm., 2012, vol. 345, p. 155.

    Article  CAS  Google Scholar 

  11. Witherington, J., Bordas, V., Garland, S.L., Hickey, D.M.B., Ife, R.J., Liddle, J., Saunders, M., Smith, D.G., and Ward, R.W., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 1577.

    Article  CAS  Google Scholar 

  12. Witherington, J., Bordas, V., Gaiba, A., Naylor, A., Rawlings, A.D., Slingsby, B.P., Smith, D.G., Takle, A.K., and Ward, R.W., Bioorg. Med. Chem. Lett., 2003, vol. 13, p. 3059.

    Article  CAS  Google Scholar 

  13. Ha, H.H., Kim, J.S., and Kim, B.M., Bioorg. Med. Chem. Lett., 2008, vol. 18, p. 653.

    Article  CAS  Google Scholar 

  14. Chioua, M., Samadi, A., Soriano, E., Lozach, O., Meijer, L., and Marco-Contelles, J., Bioorg. Med. Chem. Lett., 2009, vol. 19, p. 4566.

    Article  CAS  Google Scholar 

  15. Lapa, G.B., Bekker, O.B., Mirchink, E.P., Danilenko, V.N., and Preobrazhenskaya, M.N., J. Enzyme Inhib. Med. Chem., 2012, vol. 28, p. 1088.

    Article  Google Scholar 

  16. Guo, C., Guzzo, P.R., Hadden, M., Sargent, B.J., Yet, L., Kan, Y., Palyha, O., Kelly, T.M., Guan, X., Rosko, K., Gagen, K., Metzger, J.M., Dragovic, J., Lyons, K., Lin, L.S., and Nargund, R.P., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 2785.

    Article  CAS  Google Scholar 

  17. Ershov, O.V., Maksimova, V.N., Lipin, K.V., Belikov, M.Yu., Ievlev, M.Yu., Tafeenko, V.A., and Nasakin, O.E., Tetrahedron, 2015, vol. 71, p. 7445.

    Article  CAS  Google Scholar 

  18. Lipin, K.V., Maksimova, V.N., Ershov, O.V., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2010, vol. 46, p. 617.

    Article  CAS  Google Scholar 

  19. Belikov, M.Yu., Ievlev, M.Yu., Ershov, O.V., Lipin, K.V., Legotin, S.A., and Nasakin, O.E., Russ. J. Org. Chem., 2014, vol. 50, p. 1372.

    Article  CAS  Google Scholar 

  20. Ershov, O.V., Lipin, K.V., Maksimova, V.N., Eremkin, A.V., Kayukov, Ya.S., and Nasakin, O.E., Russ. J. Org. Chem., 2009, vol. 45, p. 475.

    Article  CAS  Google Scholar 

  21. Maksimova, V.N., Ershov, O.V., Lipin, K.V., Eremkin, A.V., and Nasakin, O.E., Russ. J. Org. Chem., 2012, vol. 48, p. 426.

    Article  CAS  Google Scholar 

  22. Ershov, O.V., Maksimova, V.N., Ievlev, M.Yu., Belikov, M.Yu., Khayarov, Kh.R., and Nasakin, O.E., Russ. J. Org. Chem., 2015, vol. 51, p. 1668.

    Article  CAS  Google Scholar 

  23. Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    Article  CAS  Google Scholar 

  24. Brandenburg, K., DIAMOND, Release 2.1d, Bonn, Germany: Crystal Impact, 2000.

    Google Scholar 

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Authors and Affiliations

  1. I.N. Ul’yanov Chuvash State University, Moskovskii pr. 15, Cheboksary, 428015, Russia

    V. N. Maksimova, A. I. Naidenova, O. V. Ershov & O. E. Nasakin

  2. Faculty of Chemistry, Moscow State University, Leninskie gory 1, Moscow, 119991, Russia

    V. A. Tafeenko

Authors
  1. V. N. Maksimova
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  2. A. I. Naidenova
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  3. O. V. Ershov
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  4. O. E. Nasakin
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  5. V. A. Tafeenko
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Corresponding author

Correspondence to O. V. Ershov.

Additional information

Original Russian Text © V.N. Maksimova, A.I. Naidenova, O.V. Ershov, O.E. Nasakin, V.A. Tafeenko, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 12, pp. 1837–1841.

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Maksimova, V.N., Naidenova, A.I., Ershov, O.V. et al. Synthesis of 3-aminopyrazolo[3,4-b]pyridine-4-carbonitriles. Russ J Org Chem 52, 1830–1834 (2016). https://doi.org/10.1134/S1070428016120204

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  • DOI: https://doi.org/10.1134/S1070428016120204

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