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Russian Chemical Bulletin

, Volume 44, Issue 11, pp 2019–2025 | Cite as

Phase transfer catalysis in the chemistry of five-membered nitrogen-containing heterocycles

  • G. I. Koldobskii
Reviews

Abstract

The methods for synthesis and reactions of five-membered nitrogen-containing heterocycles under the conditions of phase transfer catalysis as well as the application of quaternized heterocycles as phase transfer catalysts are discussed.

Key words

phase transfer catalysis phase transfer catalysts five-membered nitrogen-containing heterocycles quaternized nitrogen-containing heterocycles 

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References

  1. 1.
    R. J. Gallo, H. J. M. Dou, and P. Hassanaly,Bull. Soc. Chem. Belg., 1981,90, 849.Google Scholar
  2. 2.
    G. I. Koldobskii, V. A. Ostrovskii, and T. F. Osipova,Khim. Geterotsikl. Soedin., 1983, 1443 [Chem- Heterocycl. Compd., 1983 (Engl. Transl.)].Google Scholar
  3. 3.
    R. J. Gallo, M. Makosza, H. J. M. Dou, and P. Hassanaly, in:Advances in Heterocyclic Chemistry, Ed. A. R. Katritzky, Academic Press, New York, London, 1984,36, 175.Google Scholar
  4. 4.
    Yu. Sh. Gol'dberg,Izbrannye glavy mezhfaznogo kataliza [Selected Chapters on Phase Transfer Catalysis], Zinatne, Riga, 1989, 554 (in Russian).Google Scholar
  5. 5.
    Yu. Goldberg,Selected Problems of Phase Transfer Catalysis, Gordon and Breach, Science Publ., New York, 1992, 356.Google Scholar
  6. 6.
    W. E. Keller,Phase-Transfer Reactions, Fluka-Compendium, Georg Thieme Verlag, Stuttgart, New York, 1986,1, 415.Google Scholar
  7. 7.
    W. E. Keller,Phase-Transfer Reactions, Fluka-Compendium, Georg Thieme Verlag, Stuttgart, New York, 1987,2, 1067.Google Scholar
  8. 8.
    W. E. Keller,Phase-Transfer Reactions, Fluka-Compendium, Georg Thieme Verlag, Stuttgart, New York, 1992,3, 1080.Google Scholar
  9. 9.
    G. Wittig and U. Schoch-Grubler,Liebigs Ann. Chem., 1978, 362.Google Scholar
  10. 10.
    A. F. Khlebnikov, M. S. Novikov, and R. R. Kostikov,Khim. Geterotsikl. Soedin., 1987, 1336 [Chem. Heterocycl. Compd., 1987 (Engl. Transl.)].Google Scholar
  11. 11.
    T. Kitamura, S. Kobayashi, and H. Taniguchi,J. Org. Chem., 1984,49, 4755.Google Scholar
  12. 12.
    J. Yaozhang, Z. Changyou, W. Shengde, C. Daimo, M. Youan, and L. Guilan,Tetrahedron, 1988,44, 5343.Google Scholar
  13. 13.
    A. Jonczyk, Z. Ochal, and M. Makosza,Synthesis, 1987, 882.Google Scholar
  14. 14.
    N. N. Suvorov, D. N. Plutitskii, and Yu. I. Smushkevich,Khim. Geterotsikl. Soedin., 1981. 365 [Chem. Heterocycl. Compd., 1981 (Engl. Transl.)].Google Scholar
  15. 15.
    S. M. Shostakovskii, V. P. Mochalov, T. K. Voropaeva, V. M. Shostakovskii, and O. M. Nefedov,Izv. Akad. Nauk SSSR, Ser. Khim., 1985, 231 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1985,34, 218 (Engl. Transl.)].Google Scholar
  16. 16.
    C. Baldoli, L. Lattuada, E. Licandro, S. Maiorana, and A. Papagni,J. Heterocycl. Chem., 1989,26, 241.Google Scholar
  17. 17.
    R. A. Bartsch and Il-Woo Yang,J. Heterocycl. Chem., 1984,21, 1063.Google Scholar
  18. 18.
    S. P. J. M. Nispen, J. H. Bregman, D. G. Engen, A. M. Leusen, H. Saikachi, T. Kitagawa, and H. Sasaki,Recl. Trav. Chim. Pays-Bas, 1982,101, 28.Google Scholar
  19. 19.
    T. Okawara, Y. Tateyama, T. Yamasaki, and M. Furukawa,Chem. Express, 1986.1, 583.Google Scholar
  20. 20.
    T. Okawara, Y. Tateyma, T. Yamasaki, and M. Furukawa,J. Heterocycl. Chem., 1988,25, 1071.Google Scholar
  21. 21.
    I. V. Nikonova, G. I. Koldobskii, A. B. Zhivich, and V. A. Ostrovskii,Zh. Obshch, Khim., 1991,61, 1483 [J. Gen. Chem. USSR, 1991,61 (Engl. Transl.)].Google Scholar
  22. 22.
    I. V. Nikonova, G. I. Koldobskii, A. B. Zhivich, and V. A. Ostrovskii,Zh. Obshch, Khim., 1991,61, 2104 [J. Gen. Chem. USSR, 1991,61 (Engl. Transl.)].Google Scholar
  23. 23.
    G. I. Koldobskii, A. B. Zhivich, and V. A. Ostrovskii,Zh. Obshch, Khim., 1992,62, 3 [J. Gen. Chem. USSR, 1992,62 (Engl. Transl.)].Google Scholar
  24. 24.
    G. I. Koldobskii, Yu. E. Myznikov, A. B. Zhivich, V. A. Ostrovskii, and V. S. Poplavskii,Khim. Geterotsikl. Soedin., 1992,62, 754 [Chem. Heterocycl. Compd., 1992,62 (Engl. Transl.)].Google Scholar
  25. 25.
    G. I. Koldobskii and V. A. Ostrovskii,Usp. Khim., 1994,63, 847 [Russ. Chem. Rev., 1994,63, 797 (Engl. Transl.)].Google Scholar
  26. 26.
    A. B. Zhivich, Yu. E. Myznikov, G. I. Koldobskii, and V. A. Ostrovskii,Zh. Obshch. Khim., 1988,58, 1906 [J. Gen. Chem. USSR, 1988,58 (Engl. Transl.)].Google Scholar
  27. 27.
    T. Diez-Barra, A. de la Hoz, A. Sanchez-Migallon, P. Sanchez-Verdu, G. Bram, A. Loupy, M. Pedoussaut, and P. Pigeon,Synth. Commun., 1989,19, 293.Google Scholar
  28. 28.
    Y. Benito, L. Canoira, J. G. Rodriguez, and F. Temprano,J. Chem. Soc., Perkin Trans. II, 1987, 423.Google Scholar
  29. 29.
    R. S. Davidson, A. Satdar, J. D. Spencer, and S. Robinson,Ultrasonics, 1987,25, 35.Google Scholar
  30. 30.
    C. Gonzales and R. Greenhouse,Heterocycles, 1985,23, 1127.Google Scholar
  31. 31.
    E. Toja, A. De Paoli, G. Tuan, and J. Kettenring,Synthesis, 1987, 272.Google Scholar
  32. 32.
    K. Faber, H. J. Anderson, C. E. Loader, and A. S. Daley,Can. J. Chem., 1984,62, 1046.Google Scholar
  33. 33.
    E. Wenkert, P. D. R. Moeller, S. R. Piettre, and A. T. McPhail,J. Org. Chem., 1988,53, 3170.Google Scholar
  34. 34.
    A. A. Golan and T. V. Lee,Tetrahedron Lett., 1986, 4995.Google Scholar
  35. 35.
    E. V. Dehmlowand and Y. R. Rao,Synth. Commun., 1988,18, 487.Google Scholar
  36. 36.
    S. Julia, C. Martinez-Martorell, and J. Elguero,Heterocycles, 1986,24, 2233.Google Scholar
  37. 37.
    G. V. Asratyan, O. S. Attaryan, A. S. Pogosyan, G. A. Aliazyan, E. G. Darbinyan, and S. G. Matsoyan,Zh. Prikl. Khim., 1986,59, 1296 [J. Appl. Chem. USSR, 1986,59 (Engl. Transl.)].Google Scholar
  38. 38.
    J. Torres, J. L. Lavandera, P. Cabildo, R. M. Claramunt, and J. Elguero,J. Heterocycl. Chem., 1988,25, 771.Google Scholar
  39. 39.
    M. Lissel,Liebigs Ann. Chem., 1987, 77.Google Scholar
  40. 40.
    E. V. Dehmlow, R. Richter, and A. B. Zhivich,J. Chem. Res.(S), 1993, 504.Google Scholar
  41. 41.
    Z.-Z. Liu, H.-C. Chen, S.-L. Cao, and R.-T. Li,Synth. Commun., 1993,23, 2611.Google Scholar
  42. 42.
    P. R. Kumar,Indian J. Chem., 1986,258, 1273.Google Scholar
  43. 43.
    K. Waisser, J. Kunes, A. Hrabalek, and M. Machacek,Proc. XI Symposium on Chemistry of Heterocyclic Compounds, Prague, 1993, 68.Google Scholar
  44. 44.
    G. I. Koldobskii, I. V. Nikonova, A. B. Zhivich, V. A. Ostrovskii, and V. S. Poplavskii,Zh. Obshch. Khim., 1992,62, 194 [J. Gen. Chem. USSR, 1992,62 (Engl. Transl.)].Google Scholar
  45. 45.
    S. E. Ivanova, G. I. Koldobskii, and V. A. Ostrovskii,Khim. Geterotsikl. Soedin., 1993,63, 907 [Chem. Heterocycl. Compd., 1993,63 (Engl. Transl.)].Google Scholar
  46. 46.
    G. Koldobskii, S. Ivanova, I. Nikonova, A. Zhivich, and V. Ostrovskii,Acta Chem. Scand., 1994,48, 596.Google Scholar
  47. 47.
    H. M. Gilow,Tetrahedron Lett., 1986, 4689.Google Scholar
  48. 48.
    J. Pielichowski and D. Bodgal,J. Prakt. Chem., 1989,331, 145.Google Scholar
  49. 49.
    M. L. Cerrada, J. Elguero, J. de la Fuente, C. Pardo, and M. Ramos,Synth. Commun., 1993,23, 1947.Google Scholar
  50. 50.
    Ger. Offen. 3620430,Chem. Abstr., 1988,108, 112461f.Google Scholar
  51. 51.
    P. Kadaba,J. Prakt. Chem., 1982,324, 857.Google Scholar
  52. 52.
    C. A. Adams, C. M. Sharts, and S. A. Shackelford,Tetrahedron Lett., 1993, 6669.Google Scholar
  53. 53.
    Freedman,Pure Appl. Chem., 1986,58, 857.Google Scholar
  54. 54.
    C. L. Liotta, E. M. Burgess, C. C. Ray, E. D. Black, and B. E. Fair,Phase-Transfer Catalysis. New Chemistry, Catalysts, and Applications, Ed. C. M. Starks, American Chemical Society, Washington, 1987.Google Scholar
  55. 55.
    K. K. Park, C. H. Oh, and W. K. Joung,Tetrahedron Lett., 1993, 7445.Google Scholar
  56. 56.
    Israel Pat., 63868,Chem. Abstr., 1986,104, 168100x.Google Scholar
  57. 57.
    W. Tagaki and H. Hara,J. Chem. Soc., Chem. Commun., 1973, 891.Google Scholar
  58. 58.
    W. Tagaki, Y. Tamura, and Y. Yano,Bull. Chem. Soc. Jpn., 1980,53, 478.Google Scholar
  59. 59.
    T. F. Osipova, G. I. Koldobskii, V. A. Ostrovskii, and Yu. E. Myznikov,Khim. Geterotsikl. Soedin., 1985, 841 [Chem. Heterocycl. Compd., 1985 (Engl. Transl.)].Google Scholar
  60. 60.
    A. I. Bulachkova, G. I. Koldobskii, A. G. Drozdetskii, and G. F. Tereshchenko,Zh. Obshch. Khim., 1993,63, 907 [J. Gen. Chem., 1993,63 (Engl. Transl.)].Google Scholar
  61. 61.
    I. Kulich, M. Adamek, A. B. Zhivich, G. I. Koldobskii, and Yu. E. Myznikov,Zh. Obshch. Khim., 1990,60, 2370 [J. Gen. Chem. USSR, 1990,60 (Engl. Transl.)].Google Scholar
  62. 62.
    I. M. Rostomyan, A. G. Israelyan, V. A. Matosyan, and G. A. Chukhardzhan,Arm. Khim. Zh., 1984,37, 719 [Arm. Chem. J., 1984 (in Russian)].Google Scholar
  63. 63.
    N. Furukawa, S. Ogawa, and T. Kamai,J. Chem. Soc., Perkin Trans. I, 1984, 1833.Google Scholar
  64. 64.
    W. K. Fife and Y. Xin,J. Am. Chem. Soc., 1987,109, 1278.Google Scholar
  65. 65.
    E. V. Dehmlow, P. Singh, and J. Heider,J. Chem. Res. Synop., 1981, 292.Google Scholar
  66. 66.
    P. Singh and G. Arora,Indian J. Chem., 1986,25B, 1034.Google Scholar
  67. 67.
    D. Mohajer and S. Tangestaninejad,J. Chem. Soc., Chem. Commun., 1993, 240.Google Scholar
  68. 68.
    B. Zaldman, Y. Sasson, and R. Neumann,Ind. Eng. Chem., Prod. Res. Dev., 1985,24, 390.Google Scholar

Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • G. I. Koldobskii
    • 1
  1. 1.St. Petersburg State Institute of TechnologySt. PetersburgRussian Federation

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