Skip to main content
Log in

4h-1,3-oxazines and N-3-oxoalkylamides: Methods of production and properties (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data on the methods of synthesis and the properties of N-3-oxoalkylamides and 4H-1,3-oxazines not containing functional groups in the heterocycle are reviewed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. A. Wöhl, Berichte,34, 1914 (1901).

    Google Scholar 

  2. S. Gabriel, Lieb. Ann. Chem.,409, 305 (1915).

    Google Scholar 

  3. N. Cromwell, Heterocyclic Compounds [Russian translation], R. Elderfield (ed.), Vol. 6, IL, Moscow, (1960), p. 406.

    Google Scholar 

  4. Z. Eckstein and T. Urbansky, Advances in Heterocyclic Chemistry, A. R. Katritzky and A. J. Boulton (eds.), Vol. 2, Academic Press, New York-London (1963), p. 311.

    Google Scholar 

  5. Z. Eckstein and T. Urbansky, Advances in Heterocyclic Chemistry, A. R. Katritzky and A. J. Boulton (eds), Vol. 23, Academic Press, New York-London (1978), p. 1.

    Google Scholar 

  6. R. R. Schmidt, Synthesis, No. 7, 333 (1972).

    Google Scholar 

  7. T. Kato, N. Katagiri, and Y. Yamamoto, Heterocycles,14, 1333 (1980).

    Google Scholar 

  8. I. P. Yakovlev, A. V. Prep'yalov, and B. A. Ivin, Khim. Geterotsikl. Soedin., No. 3, 291 (1994).

    Google Scholar 

  9. H. Zaugg and B. Martin, Organic Reactions [Russian translation], I. F. Lutsenko (ed.), Vol. 14, Mir, Moscow (1967), p. 65.

    Google Scholar 

  10. H. E. Zaugg, Synthesis, No. 2, 49 (1970).

    Google Scholar 

  11. H. E. Zaugg, Synthesis, No. 2, 85 (1984).

    Google Scholar 

  12. H. E. Zaugg, Synthesis, No. 2, 171 (1984).

    Google Scholar 

  13. I. D. Gridnev and N. A. Gridneva, Usp. Khim.,64, 1091 (1995).

    Google Scholar 

  14. M. E. Smith and H. Adkins, J. Am. Chem. Soc.,60, 407 (1938).

    Google Scholar 

  15. M. Lora-Tamayo, R. Madronero, and H. Leipprand, Chem. Ber.,97, 2244 (1964).

    Google Scholar 

  16. A. S. Fisyuk [Fissyuk], M. A. Vorontsova, and R. S. Sagitullin, Mendeleev Comm., No. 6, 249 (1993).

    Google Scholar 

  17. A. S. Fisyuk and M. A. Vorontsova, Khim. Geterotsikl. Soedin., No. 2, 220 (1998).

    Google Scholar 

  18. B. V. Unkovskii, G. P. Chernysh, and Yu. B. Kazantsev, USSR Inventor's Certificate No. 196781; Chem. Abstr.,68, 49305 (1968).

    Google Scholar 

  19. H. J. Roth and Ch. Schwenke, Arch. Pharm.,297, 773 (1964); Chem. Abstr.,62, 7725 (1965).

    Google Scholar 

  20. D. Ben-Ishai, R. Moshenberg, and J. Altman, Tetrahedron,33, 1533 (1977).

    Google Scholar 

  21. J. I. Ritter, US Patent No. 2,573,673; Chem. Abstr.,46, 9584 (1952).

    Google Scholar 

  22. P. J. Scheuer, H. C. Botelho, and C. Pauling, J. Org. Chem.,22, 674 (1957).

    Google Scholar 

  23. H. Junek and G. Stolz, Monatsh. Chem.,101, 1234 (1970).

    Google Scholar 

  24. M. Lora-Tamayo, R. Madronero, G. G. Munoz, and H. Leipprand, Chem. Ber.,97, 2234 (1964).

    Google Scholar 

  25. R. R. Schmidt, Chem. Ber.,98, 334 (1965).

    Google Scholar 

  26. R. R. Schmidt, Chem. Ber.,98, 3892 (1965).

    Google Scholar 

  27. A. S. Fisyuk, M. A. Vorontsova, and S. A. Ivanov, Khim. Geterotsikl. Soedin., No. 6, 812 (1994).

    Google Scholar 

  28. E. Ghera, R. Maurya, and A. Hassner, Tetrahedron Lett.,30, 4741 (1989).

    Google Scholar 

  29. J. C. Jochims, R. Abu-El-Halawa, M. O. Glocker, L. Zsolnai, and G. Huttner, Synthesis, No. 9, 763 (1990).

    Google Scholar 

  30. S. V. Borodaev, O. V. Zubkova, N. V. Shibaeva, A. I. Pyshchev, and S. M. Luk'yanov, Khim. Geterotsikl. Soedin., No. 4, 568 (1991).

    Google Scholar 

  31. L. Monti, Gazz. Chim. Ital.60, 39 (1930); Chem. Abstr.,24, 4013 (1930).

    Google Scholar 

  32. H. Hellmann, Angew. Chem.,69, 463 (1957).

    Google Scholar 

  33. H. Hellmann, G. Aichinger, and H.-P. Wiedemann Lieb. Ann. Chem.,626, 35 (1959).

    Google Scholar 

  34. G. Stefanovic and M. Stefanovic, J. Org. Chem.,17, 1114 (1952).

    Google Scholar 

  35. V. K. Pandey, Curr. Sci.,50, 678 (1981).

    Google Scholar 

  36. D. Ben-Ishai, Z. Berler, and J. Altman, J. Chem. Soc. Chem. Commun., No. 22, 905 (1975).

    Google Scholar 

  37. D. Ben-Ishai, J. Altman, Z. Bernstein, and N. Peled, Tetrahedron,34, 467 (1978).

    Google Scholar 

  38. A. R. Katritzky and P. Harris, Tetrahedron,46, 987 (1990).

    Google Scholar 

  39. D. Matthies, Arch. Pharm.,301, 867 (1968).

    Google Scholar 

  40. D. Matthies and K. Hain, Synthesis, No. 3, 154 (1973).

    Google Scholar 

  41. H. Hellmann and G. Haas, Chem. Ber.,90, 1357 (1957).

    Google Scholar 

  42. Y. Ozaki, T. Iwasaki, M. Miyoshi, and K. Mitsumoto, J. Org. Chem.,44, 1714 (1979).

    Google Scholar 

  43. C. Ivanov, A. Dobrev, L. Nechev, and T. Nikiforov, Synth. Commun.,19, 297 (1989).

    Google Scholar 

  44. H. Böhme, Chem. Ber.,92, 1599 (1959).

    Google Scholar 

  45. Yu. V. Zeifman, N. P. Gambaryan, L. A. Simonyan, R. B. Minasyan, and I. L. Knunyants, Zh. Obshch. Khim.,37, 2476 (1967).

    Google Scholar 

  46. A. Warshawsky and D. Ben-Ishai, J. Heterocycl. Chem.,7, 917 (1970).

    Google Scholar 

  47. D. Ben-Ishai, Z. Inbal, and A. Warshawsky, J. Heterocycl. Chem.,7, 615 (1970).

    Google Scholar 

  48. A. Warshawsky and D. Ben-Ishai, Tetrahedron Lett., No. 5, 541 (1968).

    Google Scholar 

  49. A. Warshawsky and D. Ben-Ishai, J. Heterocycl. Chem.,6, 681 (1969).

    Google Scholar 

  50. M. M. Reddy, B. Bhatia, and J. Iqbal, Tetrahedron Lett.,36, 4877 (1995).

    Google Scholar 

  51. A. D. Sinitsa, B. S. Drach, and A. A. Kisenko, Zh. Org. Khim.,9, 685 (1973).

    Google Scholar 

  52. Yu. A. Arbuzov, E. I. Klimova, N. D. Antonova, and Yu. V. Tomilov, Zh. Org. Khim.,10, 1164 (1974).

    Google Scholar 

  53. N. P. Gambaryan and Yu. V. Zeifman, Izv. Akad. Nauk. SSSR. Ser. Khim.,9, 2059 (1969).

    Google Scholar 

  54. K. Bowden, G. Crank, and W. J. Ross, J. Chem. Soc. C, No. 2, 172 (1968).

    Google Scholar 

  55. R. R. Schmidt, Angew. Chem.,81, 576 (1969).

    Google Scholar 

  56. K. Ikeda, Y. Terao, and M. Sekiya, Chem. Pharm. Bull.,29, 1156 (1981).

    Google Scholar 

  57. K. Ikeda, T. Morimoto, Y. Terao, and M. Sekiya, Heterocycles,16, 131 (1981).

    Google Scholar 

  58. T. Shono, Y. Matsumura, and K. Tsubata, J. Am. Chem. Soc.,103, 1172 (1981).

    Google Scholar 

  59. K. T. Wanner and A. Kärtner, Heterocycles,26, 921 (1987).

    Google Scholar 

  60. Sh. Kobayashi, H. Ishitani, S. Komiyama, D. C. Oniciu, and A. R. Katritzky, Tetrahedron Lett.,37, 3731 (1996).

    Google Scholar 

  61. R. R. Schmidt, Angew. Chem.,85, 235 (1973).

    Google Scholar 

  62. R. R. Schmidt, Angew. Chem.,77, 218 (1965).

    Google Scholar 

  63. A. R. Katritzky, J. Pernak, and W.-Q. Fan, J. Prakt. Chem.,334, 114 (1992).

    Google Scholar 

  64. A. V. Shastin and E. S. Balenkova, Zh. Org. Khim.,20, 1357 (1984).

    Google Scholar 

  65. I. D. Gridnev, A. V. Shastin, and E. S. Balenkova, Zh. Org. Khim.,23, 1546 (1987).

    Google Scholar 

  66. I. D. Gridnev, A. V. Buevich, N. M. Sergeev, and E. S. Balenkova, Tetrahedron Lett.,30, 1987 (1989).

    Google Scholar 

  67. I. D. Gridnev, A. V. Shastin and E. S. Balenkova, Tetrahedron,47, 5577 (1991).

    Google Scholar 

  68. I. D. Gridnev and E. S. Balenkova, Zh. Org. Khim.,26, 50 (1990).

    Google Scholar 

  69. A. I. Meyers, Heterocycles in Organic Synthesis, Wiley-Interscience, New York (1974), p. 201.

    Google Scholar 

  70. R. R. Schmidt, Angew. Chem., Int. Ed.,10, 572 (1971).

    Google Scholar 

  71. R. R. Schmidt, Angew. Chem., Int. Ed.,14, 581 (1975).

    Google Scholar 

  72. R. R. Schmidt, Angew. Chem.,85, 235 (1973).

    Google Scholar 

  73. A. S. Fisyuk, M. A. Vorontsova, T. V. Leus, and R. S. Sagitullin, Fifth All-Union Conference on the Chemistry of Nitrogen-Containing Heterocyclic Compounds. Abstracts [in Russian], Chernogolovka (1991), p. 85.

  74. N. Ohba, A. Ikeda, K. Matsunari, Y. Yamada, M. Hirata, Y. Nakamura, A. Takeuchi, and H. Karino, EP Patent No. 372, 586; Chem. Abstr.,114, 247145 (1991.

    Google Scholar 

  75. A. S. Fisyuk, M. A. Vorontsova, A. É. Gatsenko, A. V. Kurilenko, L. S. Épil'dimov, and R. S. Sagitullin, Russian Federation Patent No. 1,766,917; Byull. Izobret., No. 37 (1992).

  76. Y. Kawamura, E. Oya, K. Itoh, and H. Kita, WO Patent No. 9,407,857. Chem. Abstr.,121, 230667 (1994).

    Google Scholar 

  77. A. S. Fisyuk, N. V. Poendaev, and Yu, G, Bundel', Khim. Geterotsikl. Soedin. (1998), in press.

  78. A. S. Fisyuk, N. V. Poendaev, and Yu, G, Bundel', Khim. Geterotsikl. Soedin., No. 2, 281 (1998).

    Google Scholar 

  79. A. S. Fisyuk, M. A. Vorontsova, N. V. Poendaev, and R. S. Sagitullin, Interinstitute Colloquium on the Chemistry of Nitrogen Heterocycles [in Russian], Chernogolovka (1995), p. 92.

  80. A. S. Fisyuk [Fissyuk], M. A. Vorontsova, and D. V. Temnikov, Tetrahedron Lett.,37, 5203 (1996).

    Google Scholar 

  81. A. S. Fisyuk, M. A. Vorontsova, and D. V. Temnikov, Khim. Geterotsikl. Soedin., No. 12, 1688 (1997).

    Google Scholar 

  82. A. S. Fisyuk and M. A. Vorontsova, Khim. Geterotsikl. Soedin., No. 1, 73 (1998).

    Google Scholar 

  83. A. S. Fisyuk, L. V. Berdovich, D. V. Temnikov, and L. N. Knyaz'kova, Khim. Geterotsikl. Soedin., No. 7, 921 (1997).

    Google Scholar 

  84. D. Barton and W. D. Ollis (eds.), Comprehensive Organic Chemistry. Vol. 9. Oxygen-Containing, Sulfur-Containing, and Other Heterocycles [Russian translation], P. G. Samms (ed.), Khimiya, Moscow (1985), p. 607.

    Google Scholar 

  85. R. R. Schmidt, D. Schwille, and S. Sommer, Lieb. Ann. Chem.,723, 111 (1969).

    Google Scholar 

  86. V. É. Zakhs, I. P. Yakovlev, and B. A. Ivin, Khim. Geterotsikl. Soedin., No. 11, 1443 (1987).

    Google Scholar 

  87. W. L. Schinski, I. C. Huang, and D. Ch. K. Chan, German Patent No. 2,911,865; Chem. Abstr.,92, 110677 (1980).

    Google Scholar 

  88. A. S. Moskovkin, A. P. Guzaev, I. V. Miroshnichenko M. Ya. Botnikov, and B. V. Unkovskii, Khim. Geterotsikl. Soedin., No. 11, 1539 (1988).

    Google Scholar 

Download references

Authors

Additional information

Omsk State University, Omsk 644077, Russia. Translated from Khimiya Geterotskiklicheskikh Soedinenii, No. 6, pp. 723–741, June, 1998.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fisyuk, A.S., Vorontsova, M.A. 4h-1,3-oxazines and N-3-oxoalkylamides: Methods of production and properties (review). Chem Heterocycl Compd 34, 629–645 (1998). https://doi.org/10.1007/BF02252268

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02252268

Keywords

Navigation