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Three-component spiro heterocyclization of 1H-pyrrole-2,3-diones with malononitrile and pyrazolones. Crystal and molecular structure of a spiro[pyrano[2,3-c]-pyrazole-4,3′-pyrrole]

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Abstract

5-Phenyl-1H-pyrrole-2,3-diones reacted with malononitrile and 1H-pyrazole-5(4H)-ones to give substituted 6-amino-5-cyano-2′-oxo-5′-phenyl-1′,2′-dihydro-1H-spiro[pyrano[2,3-c]pyrazole-4,3′-pyrroles]. The crystal and molecular structures of ethyl 6-amino-1,1′-dibenzyl-5-cyano-3-methyl-2′-oxo-5′-phenyl-1′,2′-dihydro-1H-spiro[pyrano[2,3-c]pyrazole-4,3′-pyrrole]-4′-carboxylate were determined by X-ray analysis.

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References

  1. Dmitriev, M.V., Silaichev, P.S., Aliev, Z.G., and Maslivets, A.N., Russ. J. Org. Chem., 2011, vol. 47, p. 1165.

    Article  CAS  Google Scholar 

  2. Silaichev, P.S., Melyukhin, R.V., Stepanyan, Yu.G., and Maslivets, A.N., Russ. J. Org. Chem., 2012, vol. 48, p. 299.

    Article  CAS  Google Scholar 

  3. Dmitriev, M.V., Silaichev, P.S., and Maslivets, A.N., Russ. J. Org. Chem., 2011, vol. 47, p. 1263.

    Article  CAS  Google Scholar 

  4. Mishriky, N., Girgis, A.S., Asaad, F.M., Ibrahim, Y.A., Sobieh, U.I., and Fawzy, N.G., Boll. Chim. Farm., 2001, vol. 140, p. 129.

    CAS  Google Scholar 

  5. Mandha, S.R., Siliveri, S., Alla, M., Bommena, V.R., Bommineni, M.R., and Balasubramanian, S., Bioorg. Med. Chem. Lett., 2012, vol. 22, p. 5272.

    Article  CAS  Google Scholar 

  6. Zaki, M.E.A., Saliman, H.A., Hickal, O.A., and Rashad, A.E., Z. Naturforsch., Teil C, 2006, vol. 61, p. 1.

    Article  CAS  Google Scholar 

  7. Ismail, M.M.F., Khalifa, N.M., Fahmy, H.H., Nossier, E.S., and Abdulla, M.M., J. Heterocycl. Chem., 2014, vol. 51, p. 450.

    Article  CAS  Google Scholar 

  8. Bhavanarushi, S., Kanakaiah, V., Yakaiah, E., Saddanapu, V., Addlagatta, A., and Rani, J.V., Med. Chem. Res., 2013, vol. 22, p. 2446.

    Article  CAS  Google Scholar 

  9. Chobe, S.S., Kamble, R.D., Patil, S.D., Acharya, A.P., Hese, S.V., Yemul, O.S., and Dawane, B.S., Med. Chem. Res., 2013, vol. 22, p. 5197.

    Article  CAS  Google Scholar 

  10. Dmitriev, M.V., Silaichev, P.S., Melyukhin, P.V., and Maslivets, A.N., Russ. J. Org. Chem., 2014, vol. 50, p. 1549.

    Article  CAS  Google Scholar 

  11. CrysAlisPro, Version 1.171.37.33 (release 27-03-2014 CrysAlis171.NET), Agilent Technologies.

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

    Article  CAS  Google Scholar 

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Correspondence to M. V. Dmitriev.

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Original Russian Text © M.V. Dmitriev, P.S. Silaichev, T.V. Sal’nikova, P.V. Melyukhin, A.N. Maslivets, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 6, pp. 900–903.

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Dmitriev, M.V., Silaichev, P.S., Sal’nikova, T.V. et al. Three-component spiro heterocyclization of 1H-pyrrole-2,3-diones with malononitrile and pyrazolones. Crystal and molecular structure of a spiro[pyrano[2,3-c]-pyrazole-4,3′-pyrrole]. Russ J Org Chem 51, 884–887 (2015). https://doi.org/10.1134/S1070428015060111

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  • DOI: https://doi.org/10.1134/S1070428015060111

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