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Synthesis of 8,10-dimethyl-1,10b-dihydro[1,3,5]triazino-[2,1-a]isoindole-2,4,6(3H)-trione by Direct arylation of 1,3,5-triazine-2,4(1H,3H)-dione

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Abstract

Direct arylation of 1,3,5-triazine-2,4(1H,3H)-dione with mesitylene afforded a novel fused heterocyclic system, 8,10-dimethyl-1,10b-dihydro[1,3,5]triazino[2,1-a]isoindole-2,4,6(3H)-trione.

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References

  1. Blázquez, M.T., Muñiz, F.M., Sáez, S., Simón, L.M., Alonso, Á., Raposo, C., Lithgow, A., Alcázar, V., and Morán, J.R., Heterocycles, 2006, vol. 69, p. 73.

    Article  Google Scholar 

  2. Binnemans, K., Chem. Rev., 2005, vol. 105, p. 4148.

    Article  CAS  Google Scholar 

  3. Borsenberger, P.M. and Weiss, D.S., Organic Photoreceptors for Xerography, New York: Marcel Dekker, 1998, pp. 562, 584, 632.

    Google Scholar 

  4. Kopchuk, D.S., Prokhorov, A.M., Slepukhin, P.A., and Kozhevnikov, D.N., Tetrahedron Lett., 2012, vol. 53, p. 6265.

    Article  CAS  Google Scholar 

  5. Schroeder, A.C. and Bardos, T.J., J. Med. Chem., 1981, vol. 24, p. 109.

    Article  CAS  Google Scholar 

  6. Moody, D.L., Dyba, M., Kosakowska-Cholody, T., Tarasova, N.I., and Michejda, C.J., Bioorg. Med. Chem. Lett., 2007, vol. 17, p. 2380.

    Article  CAS  Google Scholar 

  7. Chernyak, D. and Gevorgyan, V., Org. Lett., 2010, vol. 12, no. 23, p. 5558.

    Article  CAS  Google Scholar 

  8. Baron, M., Waste Biomass Valoriz., 2012, vol. 3, p. 395.

    Article  Google Scholar 

  9. Egorov, I.N., Tseitler, T.A., Zyryanov, G.V., Rusinov, V.L., and Chupakhin, O.N., Arkivoc, 2011, part (x), p. 312.

    Google Scholar 

  10. Kozhevnikov, V.N., Kozhevnikov, D.N., Nikitina, T.V., Rusinov, V.L., Chupakhin, O.N., Zabel, M., and König, B., J. Org. Chem., 2003, vol. 68, p. 2882.

    Article  CAS  Google Scholar 

  11. Chupakhin, O.N. and Beresnev, D.G., Russ. Chem. Rev., 2002, vol. 71, p. no. 9, p. 707.

    Article  CAS  Google Scholar 

  12. Girke, W.P.K., Chem. Ber., 1979, vol. 112, p. 1.

    Article  CAS  Google Scholar 

  13. Girke, W.P.K., Chem. Ber., 1979, vol. 112, p. 1348.

    Article  CAS  Google Scholar 

  14. Giacomelli, G. and Porcheddu, A., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ramsden, C.A., Scriven, E.F.V., and Taylor, R.J.K., Eds., Amsterdam: Elsevier, 2008, vol. 9, p. 197.

  15. Masquelin, T., Delgado, Y., and Baumle, V., Tetrahedron Lett., 1998, vol. 39, p. 5725.

    Article  CAS  Google Scholar 

  16. Kunishima, M., Hioki, K., Wada, A., Kobayashi, H., and Tani, S., Tetrahedron Lett., 2002, vol. 43, p. 3323.

    Article  CAS  Google Scholar 

  17. Samaritani, S. and Menicagli, R., Tetrahedron, 2002, vol. 58, p. 1381.

    Article  CAS  Google Scholar 

  18. Bork, J.T., Lee, J.W., Khersonsky, S.M., Moon, H.-S., and Chang, Y.-T., Org. Lett., 2003, vol. 5, p. 117.

    Article  CAS  Google Scholar 

  19. Samaritani, S., Signore, J., Malanga, C., and Menicagli, R., Tetrahedron, 2005, vol. 61, p. 4475.

    Article  CAS  Google Scholar 

  20. Azev, Y.A., Shorshnev, S.V., and Gabel, D., Mendeleev Commun., 2001, vol. 11, p. 234.

    Article  Google Scholar 

  21. Azev, Y.A., Shorshnev, S.V., and Gabel, D., Pharm. Chem. J., 2002, vol. 36, p. 146.

    Article  CAS  Google Scholar 

  22. Egorov, I.N., Rusinov, V.L., and Chupakhin, O.N., Tetrahedron Lett., 2010, vol. 51, p. 1717.

    Article  CAS  Google Scholar 

  23. Shanmugam, P., Boobalan, P., and Perumal, P.T., Tetrahedron, 2007, vol. 63, p. 12 215.

    Article  CAS  Google Scholar 

  24. Nikalje, M. and Sudalai, A., Tetrahedron, 1999, vol. 55, p. 5903.

    Article  CAS  Google Scholar 

  25. Huisgen, R., Morikawa, M., Herbig, K., and Brunn, E., Chem. Ber., 1967, vol. 100, p. 1094.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Ural Federal University, ul. Mira 19, Yekaterinburg, 620002, Russia

    T. A. Tseitler, G. V. Zyryanov, D. S. Kopchuk, I. S. Kovalev, V. L. Rusinov & O. N. Chupakhin

  2. Postovskii Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, ul. S. Kovalevskoi/Akademicheskaya 22/20, Yekaterinburg, 620990, Russia

    G. V. Zyryanov, D. S. Kopchuk, V. L. Rusinov & O. N. Chupakhin

Authors
  1. T. A. Tseitler
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  2. G. V. Zyryanov
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  3. D. S. Kopchuk
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  4. I. S. Kovalev
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  5. V. L. Rusinov
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  6. O. N. Chupakhin
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Corresponding author

Correspondence to G. V. Zyryanov.

Additional information

Original Russian Text © T.A. Tseitler, G.V. Zyryanov, D.S. Kopchuk, I.S. Kovalev, V.L. Rusinov, O.N. Chupakhin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 6, pp. 801–803.

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Tseitler, T.A., Zyryanov, G.V., Kopchuk, D.S. et al. Synthesis of 8,10-dimethyl-1,10b-dihydro[1,3,5]triazino-[2,1-a]isoindole-2,4,6(3H)-trione by Direct arylation of 1,3,5-triazine-2,4(1H,3H)-dione. Russ J Org Chem 50, 783–785 (2014). https://doi.org/10.1134/S1070428014060037

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  • DOI: https://doi.org/10.1134/S1070428014060037

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