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Synthesis and Transformations of Nitrogen Heterocycles in Ionic Liquids (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

A review is given for our work in the Nitrogen Compound Laboratory of the Institute of Organic Chemistry of the Russian Academy of Sciences over the past 10 years on the use of ionic liquids as reaction media and catalysts in the 1,3-dipolar cycloaddition of various 1,3-dipoles, such as azomethine imines, azides, and nitrile oxides, including domino reactions for the expansion of the three-membered diaziridine ring in monocyclic diaziridine derivatives and condensation reactions such as the synthesis of aminothiadiazoles and dihydroisoquinolines. The Schmidt rearrangement and Henry and Mannich reactions of polynitroalkanes in ionic liquids are also discussed.

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References

  1. P. Wasserscheid and T. Welton (editors), Ionic Liquids in Synthesis, Vol. 1, Wiley-VCH Verlag, Weinheim (2008).

    Google Scholar 

  2. P. Wasserscheid and T. Welton (editors), Ionic Liquids in Synthesis, Vol. 2, Wiley-VCH Verlag, Weinheim (2008).

    Google Scholar 

  3. S. G. Zlotin and N. N. Makhova, Usp. Khim., 79, 603 (2010). [Russ. Chem. Rev., 79, 543 (2010)].

    Article  CAS  Google Scholar 

  4. N. N. Makhova, V. Yu. Petukhova, and V. V. Kuznetsov, ARKIVOC, i, 128 (2008).

  5. N. N. Makhova, A. V. Shevtsov, and V. Yu. Petukhova, Usp. Khim., 80, 1087 (2011).

    Article  Google Scholar 

  6. Yu. S. Syroeshkina, V. V. Kuznetsov, M. I. Struchkova, M. A. Epishina, and N. N. Makhova, Mendeleev Commun., 18, 207 (2008).

    Article  CAS  Google Scholar 

  7. Yu. S. Syroeshkina, I. V. Ovchinnikov, V. V. Kuznetsov, V. V. Kachala, Yu. V. Nelyubina, K. A. Lyssenko, and N. N. Makhova, Mendeleev Commun., 19, 276 (2009).

    Article  CAS  Google Scholar 

  8. Yu. S. Syroeshkina, V. V. Kuznetsov, K. A. Lyssenko, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 362 (2009). [Russ. Chem. Bull., Int. Ed., 58, 366 (2009)].

    Article  CAS  Google Scholar 

  9. Yu. S. Syroeshkina, L. L. Fershtat, V. V. Kachala, V. V. Kuznetsov, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 1579 (2010). [Russ. Chem. Bull., Int. Ed., 59, 1621 (2010)].

    Article  CAS  Google Scholar 

  10. M. I. Pleschev, V. V. Kachala, A. S. Goloveshkin, I. S. Bushmarinov, V. V. Kuznetsov, D. V. Khakimov, and N. N. Makhova, Mendeleev Commun., 23, 271 (2013).

    Article  Google Scholar 

  11. M. I. Pleschev, M. A. Epishina, V. V. Kachala, V. V. Kuznetsov, A. S. Goloveshkin, I. S. Bushmarinov, and N. N. Makhova, Mendeleev Commun., 23, 206 (2013).

    Article  Google Scholar 

  12. L. N. Jungheim and S. K. Sigmund, J. Org. Chem., 52, 4007 (1987).

    Article  CAS  Google Scholar 

  13. L. N. Jungheim, Tetrahedron Lett., 30, 1889 (1989).

    Article  CAS  Google Scholar 

  14. M. P. Clark, S. K. Laughlin, M. J. Laufersweiler, R. G. Bookland, T. A. Brugel, A. Golobiowski, M. P. Sabat, J. A. Townes, J. C. VanRens, J. F. Djung, M. G. Natehus, B. De, L. C. Hsieh, S. C. Xu, R. L. Walter, M. J. Mekel, S. A. Heitmeyer, K. K. Brown, K. Juergens, Y. O. Taiwo, and M. J. Janusz, J. Med. Chem., 47, 2724 (2004).

    Article  CAS  Google Scholar 

  15. B. Kurosu, JP Pat. Appl. 51133265.

  16. B. L. Walworth, US Pat. Appl. 4091106.

  17. P.-J. Alarco, Ya. Abu-Lebdeh, and M. Armand, Solid State Ionics, 175, 717 (2004).

    Article  CAS  Google Scholar 

  18. I. V. Seregin, I. V. Ovchinnikov, N. N. Makhova, D. V. Lyubetsky, and K. A. Lyssenko, Mendeleev. Commun., 13, 230 (2003).

    Article  Google Scholar 

  19. V. Yu. Petukhova, M. I. Pleshchev, L. L. Fershtat, V. V. Kuznetsov, V. V. Kachala, and N. N. Makhova, Mendeleev Commun., 22, 32 (2012).

    Article  CAS  Google Scholar 

  20. M. I. Pleshchev, V. Yu. Petukhova, V. V. Kuznetsov, D. V. Khakimov, T. S. Pivina, M. I. Struchkova, Yu. V. Nelyubina, and N. N. Makhova, Mendeleev Commun., 23, 34 (2013).

    Article  CAS  Google Scholar 

  21. M. I. Pleshchev, V. Yu. Petukhova, V. V. Kuznetsov, D. V. Khakimov, T. S. Pivina, Yu. V. Nelyubina, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 1065 (2013). [Russ. Chem. Bull., Int. Ed., 62, 1066 (2013)].

    Article  CAS  Google Scholar 

  22. H. Giera and R. Huisgen, Liebigs Ann./Recl., 1685 (1997).

  23. G. Bianchi, C. De Micheli, and R. Gandolfi, Angew. Chem., Int. Ed. Engl., 18, 721 (1979).

    Article  Google Scholar 

  24. I. V. Seregin, L. V. Batog, and N. N. Makhova, Mendeleev Commun., 12, 83 (2002).

    Article  Google Scholar 

  25. M. A. Epishina, A. S. Kulikov, N. V. Ignat’ev, M. Schulte, and N. N. Makhova, Mendeleev Commun., 21, 334 (2011).

    Article  CAS  Google Scholar 

  26. N. Mykola, N. N. Makhova, A. S. Kulikov, and M. E. Epishina, DE Pat. Appl. 102011014082.

  27. A. V. Shevtsov, V. V. Kuznetsov, A. A. Kislukhin, V. Yu. Petukhova, Yu. A. Strelenko, and N. N. Makhova, Mendeleev Commun., 16, 218 (2006).

    Article  Google Scholar 

  28. Yu. S. Syroeshkina, V. V. Kuznetsov, V. V. Kachala, and N. N. Makhova, J. Heterocycl. Chem., 46, 1195 (2009).

    Article  CAS  Google Scholar 

  29. V. Yu. Petukhova, L. L. Fershtat, V. V. Kachala, V. V. Kuznetsov, D. V. Khakimov, T. S. Pivina, and N. N. Makhova, J. Heterocycl. Chem., 50, 326 (2013).

    Article  CAS  Google Scholar 

  30. S. G. Zlotin and N. N. Makhova, Mendeleev Commun., 20, 63 (2010).

    Article  CAS  Google Scholar 

  31. M. A. Epishina, A. S. Kulikov, N. V. Ignat’ev, M. Schulte, and N. N. Makhova, Mendeleev Commun., 21, 331 (2011).

    Article  CAS  Google Scholar 

  32. H. Kato and M. Ohta, Nippon Kagaku Zasshi, 78, 1588 (1957). [Chem. Abstr., 54, 1502 (1960)].

    Google Scholar 

  33. M. A. Epishina, A. S. Kulikov, M. I. Struchkova, N. V. Ignat’ev, M. Schulte, and N. N. Makhova, Mendeleev Commun., 22, 267 (2012).

    Article  CAS  Google Scholar 

  34. M. A. Epishina, A. S. Kulikov, N. V. Ignat’ev, M. Schulte, and N. N. Makhova, Mendeleev Commun., 20, 335 (2010).

    Article  CAS  Google Scholar 

  35. O. A. Rakitin, O. A. Zalesova, A. S. Kulikov, N. N. Makhova, T. I. Godovikova, and L. I. Khmel’nitskii, Izv. Akad. Nauk, Ser. Khim., 1949 (1993). [Russ. Chem. Bull., 42, 1865 (1993)].

    Article  Google Scholar 

  36. A. O. Finogenov, I. V. Ovchinnikov, A. S. Kulikov, and N. N. Makhova, Izv. Akad. Nauk, Ser. Khim., 469 (2012). [Russ. Chem. Bull., 61, 472 (2012)].

    Article  CAS  Google Scholar 

  37. M. A. Epishina, I. V. Ovchinnikov, A. S. Kulikov, N. N. Makhova, and V. A. Tartakovsky, Mendeleev Commun., 21, 21 (2011).

    Article  CAS  Google Scholar 

  38. M. A. Epishina, A. O. Finogenov, A. S. Kulikov, N. N. Makhova, I. V. Anan’ev, and V. A. Tartakovsky, Izv. Akad. Nauk, Ser. Khim., 1559 (2012). [Russ. Chem. Bull., Int. Ed., 61, 1575 (2012)].

    Article  CAS  Google Scholar 

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This work was partially supported by the Russian Foundation for Basic Research (grant No. 13-03-00153a) and by Merck KGaA.

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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

    N. N. Makhova, M. I. Pleshchev, M. A. Epishina & A. S. Kulikov

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  1. N. N. Makhova
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  2. M. I. Pleshchev
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  3. M. A. Epishina
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  4. A. S. Kulikov
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Corresponding author

Correspondence to N. N. Makhova.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 690-703, May, 2014.

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Makhova, N.N., Pleshchev, M.I., Epishina, M.A. et al. Synthesis and Transformations of Nitrogen Heterocycles in Ionic Liquids (Review). Chem Heterocycl Comp 50, 634–646 (2014). https://doi.org/10.1007/s10593-014-1516-1

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  • DOI: https://doi.org/10.1007/s10593-014-1516-1

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