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Domino reactions of pyrazol-5-amines with arylglyoxals and malononitrile

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Abstract

Domino reactions of 3-methylpyrazol-5-amine and 1-phenyl-3-methylpyrazol-5-amine with arylglyoxal hydrates and malononitrile in alcohol proceed regioselectively and lead to the formation of 6-aminopyrazolo[3,4-b]pyridine-5-carbonitrile.

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References

  1. Bonne, D., Coquerel, Y., Constantieux, T., and Rodriguez, J., Tetrahedron: Asymmetry, 2010, vol. 21, p. 1085.

    Article  CAS  Google Scholar 

  2. Hugel, H., Molecules, 2009, vol. 14, p. 4936.

    Article  CAS  Google Scholar 

  3. Bariwal, J.B., Trivedi, J.C., and Van der Eycken, E.V., Top. Heterocycl. Chem., 2010, vol. 25, p. 169.

    CAS  Google Scholar 

  4. Jeanneau-Nicolle, E., Benoit-Guyod, M., and Leclerc, G., Synth. Commun., 1991, vol. 21, p. 1443.

    Article  CAS  Google Scholar 

  5. M’hamed, M.O. and Alduaij, K., Phosphorus, Sulfur, Silicon., 2014, vol. 189, p. 235.

    Article  Google Scholar 

  6. Fadda, A.A., Abd El-Latif, E., Bondock, S., and Samir, A., Synth. Commun., 2008, vol. 38, p. 4352.

    Article  CAS  Google Scholar 

  7. Raghuvanshi, D.S. and Singh, K.N., J. Heterocycl. Chem., 2011, vol. 48, p. 582.

    Article  CAS  Google Scholar 

  8. Ghodasara, H.B., Trivedi, R., Kataria, V.B., Patel, B.G., and Shah, V.H., Med. Chem. Res., 2013, vol. 22, p. 6121.

    Article  CAS  Google Scholar 

  9. Zhang, X., Li, X., Fan, X., Wang, X., Wang, J., and Qu, G., Aust. J. Chem., 2009, vol. 62, p. 382.

    Article  CAS  Google Scholar 

  10. Lipson, V.V., Shirobokova, M.G., Shishkin, O.V., and Shishkina, S.V., Russ. J. Org. Chem., 2006, vol. 42, p. 1015.

    Article  CAS  Google Scholar 

  11. Petrova, O.N., Zamigailo, L.L., Shirobokova, M.G., Shishkina, S.V., Shishkin, O.V., Musatov, V.I., and Lipson, V.V., Chem. Heterocycl. Compd., 2013, vol. 49, p. 955.

    Article  CAS  Google Scholar 

  12. Petrova, O.N., Lipson, V.V., Zamigajlo, L.L., Shirobokova, M.G., Musatov, V.I., Baumer, V.N., and Sofronov, D.S., Russ. J. Org. Chem., 2015, vol. 51, p. 1597.

    Article  CAS  Google Scholar 

  13. Lipson, V.V., Borodina, V.V., Zemlyanaya, N.I., Shirobokova, M.G., Musatov, V.I., Shishkina, S.V., and Sofronov, D.S., Russ. J. Org. Chem., 2015, vol. 51, p. 697.

    Article  CAS  Google Scholar 

  14. Lipson, V.V., Desenko, S.M., Shirobokova, M.G., Shishkin, O.V., and Shishkina, S.V., Russ. J. Org. Chem., 2006, vol. 42, p. 1022.

    Article  CAS  Google Scholar 

  15. Lipson, V.V., Karnozhitskaya, T.M., Desenko, S.M., Shishkina, S.V., Shishkin, O.V., and Musatov, V.I., Russ. J. Org. Chem., 2007, vol. 43, p. 249.

    Article  CAS  Google Scholar 

  16. Petrova, O.N., Zamigajlo, L.L., Gella, I.M., Musatov, V.I., Shishkina, S.V., Shishkin, O.V., Vashchenko, E.V., Borisov, A.V., and Lipson, V.V., Chem. Heterocycl. Compd., 2014, vol. 50, p. 514.

    Article  CAS  Google Scholar 

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Correspondence to V. V. Lipson.

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Original Russian Text © O.N. Petrova, V.V. Lipson, L.L. Zamigajlo, M.G. Shirobokova, V.I. Musatov, D.A. Dmitrienko, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 8, pp. 1176–1180.

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Petrova, O.N., Lipson, V.V., Zamigajlo, L.L. et al. Domino reactions of pyrazol-5-amines with arylglyoxals and malononitrile. Russ J Org Chem 52, 1168–1172 (2016). https://doi.org/10.1134/S1070428016080121

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  • DOI: https://doi.org/10.1134/S1070428016080121

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