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Synthesis of spiro[imidazole-2,2′-pyrroles] by reaction of 4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with urea

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Abstract

Substituted alkyl 4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with urea to give alkyl 2-(carbamoylamino)-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylates which underwent intramolecular cyclization to 8-hydroxy-1,3,6-triazaspiro[4.4]non-8-ene-2,4,7-triones by the action of sodium methoxide.

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References

  1. Andreichikov, Yu.S., Gein, V.L., Zalesov, V.V., Kozlov, A.P., Kollents, G., Maslivets, A.N., Pimenova, E.V., and Shurov, S.N., Khimiya pyatichlennykh 2,3-dioksogeterotsiklov (Chemistry of Five-Membered 2,3-Dioxo Heterocycles), Perm: Perm. Gos. Univ., 1994.

    Google Scholar 

  2. Maslivets, A.N. and Mashevskaya, I.V., 2,3-Digidro-2,3-pirroldiony (2,3-Dihydropyrrole-2,3-diones), Perm: Perm. Gos. Univ., 2005.

    Google Scholar 

  3. Aliev, Z.G., Maslivets, A.N., Mashevskaya, I.V., and Silaichev, P.S., Issledovanie dioksogeterotsiklov metodom rentgenostrukturnogo analiza (X-Ray Diffraction Study of Dioxo Heterocycles), Perm: Perm. Gos. Univ., 2012.

    Google Scholar 

  4. Maslivets, A.N., Stepanova, E.E., Dmitriev, M.V., and Konovalova, V.V., Issledovanie dioksogeterotsiklov metodom rentgenostrukturnogo analiza. Chast’ 2 (X-Ray Diffraction Study of Dioxo Heterocycles. Part 2), Perm: Perm. Gos. Univ., 2014.

    Google Scholar 

  5. Dubovtsev, A.Yu., Moroz, A.A., Dmitriev, M.V., and Maslivets, A.N., Russ. J. Org. Chem., 2016, vol. 52, p. 546.

    Article  CAS  Google Scholar 

  6. Silaichev, P.S., Chudinova, M.A., Slepukhin, P.A., and Maslivets, A.N., Russ. J. Org. Chem., 2012, vol. 48, p. 109.

    Article  CAS  Google Scholar 

  7. Denislamova, E.S., Bubnov, N.V., Aliev, Z.G., and Maslivets, A.N., Russ. J. Org. Chem., 2011, vol. 47, p. 1362.

    Article  CAS  Google Scholar 

  8. Bubnov, N.V., Denislamova, E.S., Aliev, Z.G., and Maslivets, A.N., Russ. J. Org. Chem., 2011, vol. 47, p. 523.

    Article  CAS  Google Scholar 

  9. Maslivets, A.N., Smirnova, L.I., Ivanenko, O.I., and Andreichikov, Yu.S., Russ. J. Org. Chem., 1995, vol. 31, p. 563.

    Google Scholar 

  10. Maslivets, A.N., Smirnova, L.I., and Andreichikov, Yu.S., Zh. Org. Khim., 1988, vol. 24, p. 2205.

    CAS  Google Scholar 

  11. Maslivets, A.N., Smirnova, L.I., and Andreichikov, Yu.S., Zh. Org. Khim., 1989, vol. 25, p. 1748.

    CAS  Google Scholar 

  12. Terpetschnig, E., Ott, W., Kollenz, G., Peters, K., Peters, E.M., and Schnering, H.G., Monatsh. Chem., 1988, vol. 119, p. 367.

    Article  CAS  Google Scholar 

  13. Maslivets, A.N., Smirnova, L.I., and Andreichikov, Yu.S., Zh. Org. Khim., 1992, vol. 28, p. 2141.

    Google Scholar 

  14. Tsuda, Y., Horiguchi, Y., and Sano, T., Heterocycles, 1976, vol. 7, p. 1237.

    Article  Google Scholar 

  15. Andreichikov, Yu.S., Maslivets, A.N., Smirnova, L.I., Krasnykh, O.P., Kozlov, A.P., and Perevozchikov, L.A., Zh. Org. Khim., 1987, vol. 23, p. 1534.

    CAS  Google Scholar 

  16. Mohri, K., Kanie, A., Horiguchi, Y., and Isobe, K., Heterocycles, 1999, vol. 51, p. 2377.

    Article  CAS  Google Scholar 

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Correspondence to A. N. Maslivets.

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Original Russian Text © A.Yu. Dubovtsev, P.S. Silaichev, M.A. Zheleznova, Z.G. Aliev, A.N. Maslivets, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 12, pp. 1788–1792.

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Dubovtsev, A.Y., Silaichev, P.S., Zheleznova, M.A. et al. Synthesis of spiro[imidazole-2,2′-pyrroles] by reaction of 4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates with urea. Russ J Org Chem 52, 1779–1783 (2016). https://doi.org/10.1134/S1070428016120113

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  • DOI: https://doi.org/10.1134/S1070428016120113

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