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Regioselective Synthesis of 1,5-Diaryl-2-(Hydroxyalkyl)-8-Methylglycolurils

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Chemistry of Heterocyclic Compounds Aims and scope

The cyclocondensation of N-methylurea with derivatives of tetrahydroimidazooxazolone, tetrahydro-imidazooxazinone, dihydroimidazooxazinone, and tetrahydroimidazooxazepinone was studied for the first time. It was shown that the reactions take place with high regioselectivity, are regular in character, and lead to the formation of previously inaccessible 1,5-diaryl-2-(hydroxyalkyl)-8-methylglycolurils with high yields.

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References

  1. M. D. Mashkovskii, Drugs [in Russian], Ed. 16, Vol. 1, Novaya Volna (2014), p. 83.

  2. I. S. Ryzhkina, Yu. V. Kiseleva, O. A. Mishina, A. P. Timosheva, S. Yu. Sergeeva, A. N. Kravchenko, and A. I. Konovalov, Mendeleev Commun., 23, 262 (2013).

    Article  CAS  Google Scholar 

  3. A. N. Kravchenko and Yu. A. Strelenko, Mendeleev Commun., 23, 104 (2013).

    Article  CAS  Google Scholar 

  4. E. H. Puzig, WO Pat. Appl. 8910696.

  5. S. In and J. Kang, Tetrahedron Lett., 46, 7165 (2005).

    Article  CAS  Google Scholar 

  6. J. Kang, S. In, and S. J. Cho, Supramol. Chem., 19, 243 (2007).

    Article  CAS  Google Scholar 

  7. F. Hof, S. L. Craig, C. Nuckolls, and J. Rebek, Jr., Angew. Chem., Int. Ed., 41, 1488 (2002).

    Article  CAS  Google Scholar 

  8. V. Havel, J. Svec, M. Wimmerova, M. Dusek, M. Pojarova, and V. Sindelar, Org. Lett., 13, 4000 (2011).

    Article  CAS  Google Scholar 

  9. P. Toman, E. Makrlík, and P. Vanűra, Chem. Phys. Lett., 547, 63 (2012).

    Article  CAS  Google Scholar 

  10. S. Sun, L. Edwards, and P. Harrison, J. Chem. Soc., Perkin Trans. 1, 437 (1998).

  11. M. Rahimizadeh, K. Kam, S. I. Jenkins, R. S. McDonald, and P. H. M. Harrison, Can. J. Chem., 80, 517 (2002).

    Article  CAS  Google Scholar 

  12. K. E. Pryor and J. Rebek, Jr., Org. Lett., 1, 39 (1999).

    Article  CAS  Google Scholar 

  13. D. Ma, Z. Gargulakova, P. Y. Zavalij, V. Sindelar, and L. Isaacs, J. Org. Chem., 75, 2934 (2010).

    Article  CAS  Google Scholar 

  14. M. Stancl, Z. Gargulakova, and V. Sindelar, J. Org. Chem., 77, 10945 (2012).

    Article  CAS  Google Scholar 

  15. L.-P. Cao, X.-G. Meng, J.-Y. Ding, H.-L. Xi, and A.-X. Wu, J. Chem. Crystallogr., 41, 425 (2011).

    Article  CAS  Google Scholar 

  16. J. Wang, J. Xiang, A. Wu, and X. Meng, CrystEngComm, 15, 10079 (2013).

    Article  CAS  Google Scholar 

  17. V. V. Baranov, M. M. Antonova, Yu. V. Nelyubina, N. G. Kolotyrkina, I. E. Zanin, and A. N. Kravchenko, Mendeleev Commun. DOI 10.1016/j.mencom.2014.04.015.

  18. D. W. Johnson, L. C. Palmer, F. Hof, P. M. Iovine, and J. Rebek, Jr., Chem. Commun., 2228 (2002).

  19. A. R. Butler and E. Leitch, J. Chem. Soc., Perkin Trans. 2, 103 (1980).

  20. A.-X. Wu, J. C. Fettinger, and L. Isaacs, Tetrahedron, 58, 9769 (2002).

    Article  CAS  Google Scholar 

  21. A. N. Kravchenko, V. V. Baranov, G. A. Gazieva, I. E. Chikunov, and Yu. V. Nelyubina, Izv. Akad. Nauk, Ser. Khim., 416 (2014).

  22. M. Jasiński, G. Mlostoń, P. Mucha, A. Linden, and H. Heimgartner, Helv. Chim. Acta, 90, 1765 (2007).

    Article  Google Scholar 

  23. A. N. Kravchenko, E. Yu. Maksareva, P. A. Belyakov, A. S. Sigachev, K. Yu. Chegaev, K. A. Lysenko, O. V. Lebedev, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 180 (2003). [Russ. Chem. Bull., 52, 192 (2003).]

    Article  CAS  Google Scholar 

  24. O. L. Brady and M. M. Muers, J. Chem. Soc., 216 (1930).

  25. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

    Article  Google Scholar 

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The work was carried out with financial support from the Presidium of the Russian Academy of Sciences (program 8-P) and the Russian Foundation for Basic Research (grant 14-03-31676).

The authors express their gratitude to D. V. Khakimov for performing the quantum-chemical calculations.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow, 119991, Russia

    M. M. Antonova, V. V. Baranov & A. N. Kravchenko

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St., Moscow, 119991, Russia

    Yu. V. Nelyubina

Authors
  1. M. M. Antonova
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  2. V. V. Baranov
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  3. Yu. V. Nelyubina
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  4. A. N. Kravchenko
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Corresponding author

Correspondence to A. N. Kravchenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 551-561, April, 2014.

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Antonova, M.M., Baranov, V.V., Nelyubina, Y.V. et al. Regioselective Synthesis of 1,5-Diaryl-2-(Hydroxyalkyl)-8-Methylglycolurils. Chem Heterocycl Comp 50, 503–513 (2014). https://doi.org/10.1007/s10593-014-1501-8

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  • DOI: https://doi.org/10.1007/s10593-014-1501-8

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