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Unsaturated 1,5-diketones and their halogen-substituted derivatives — Preparation and use in the synthesis of heterocycles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Published data and the results of the authors' own research on methods for the production of unsaturated 1,5-diketones and halogen-substituted 2-pentene-1,5-diones and their use in the synthesis of difficulty obtainable pyrylium, 3,5-dichloropyrylium, and 3-chlorothiopyrylium salts, aroylfurans, 40-chloroaroylfurans, isoxazolines, pyrazolines, 3,5-dichloropyridines, 1,4-tetramethylenebispyridines, and others are summarized. Aspects of the structure of 2-pentene-1,5-diones and their 2,4-dichloro-substituted analogs and features of their heterocyclization are discussed in comparison with pentane-1,5-diones and their 2,4-dichloro-substituted derivatives.

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References

  1. W. Dilthey, J. Prakt. Chem.,94, 53 (1916).

    Google Scholar 

  2. W. Dilthey and R. Taucher, Chem. Ber.,53, 252 (1920).

    Google Scholar 

  3. I. Berson, J. Am. Chem. Soc.,74, 358 (1952).

    Google Scholar 

  4. I. P. Griot, I. Royer, and I. Dreux, Tetrahedron Lett., No. 26, 2195 (1969).

  5. A. I. Pyshchev, Thesis for Candidate of Chemical Sciences [in Russian], Rostov University, Rostov-on-Don (1977).

  6. I. I. Basselier, Ann. Chim.,6, 1131 (1961).

    Google Scholar 

  7. G. Rio and V. Fellion, Tetrahedron Lett.,25, 1213 (1962).

    Google Scholar 

  8. G. W. Fischer and M. Herrmann, J. Prakt. Chem.,326 No. No. 2, 287 (1984).

    Google Scholar 

  9. J. Becher, I. P. Jacobsen, C. Stidsen, T. Zimmermann, and G. W. Fischer, Acta Chem. Scand.,B41, 391 (1987).

    Google Scholar 

  10. A. Williams, J. Am. Chem. Soc.,93 2733 (1971).

    Google Scholar 

  11. A. I. Pyshchev, N. V. Shibaeva, S. S. Goryachev, and L. L. Pyshcheva, The Chemistry of Dicarbonyl Compounds Fifth All-Union Conference Honor of the 100th Birthday of Academician of the Academy of Sciences of the Latvian SSR Gustav Vanag. Abstracts [in Russian], Riga (1981), p. 193.

  12. A. I. Pyshchev (Pyshcev), uN. G. Bokii, and Yu. T. Struchkov, Tetrahedron,34, 2131 (1978)

    Google Scholar 

  13. Yu. A. Zhdanov, É. A Zvezdina, S. M. Statsenko, and A. N. Maksimova, Khim. Geterotsikl. Soedin., No. 2, 182 (1987).

  14. G. W. Fischer, J. Prakt. Chem.,327, 529 (1985).

    Google Scholar 

  15. L. P. Olekhnovich, I. B. Orenshtein, N. G. Tregub, G. N. Dorofeenko, and V. I. Minkin, Zh. Org. Khim.,13, 1124 (1977).

    Google Scholar 

  16. V. Fellion, Compt. Rend.,252, 207 (1961).

    Google Scholar 

  17. V. Fellion, Compt. Rend.252, 2898 (1961).

    Google Scholar 

  18. M. Simaltry, H. Streelesha, and H. Knedija, Bull. Soc. Chim. France, No. 10, 3603 (1971).

  19. P. F. Devitt, J. Chem. Soc., No. 1, 510 (1958).

  20. C. A. Henrick, E. Ritchie, and W. C. Taylor, Aust. J. Chem.,20, 2441 1967.

    Google Scholar 

  21. M. V. Nekhoroshev, V. H. Panov A. A. Bul'ber, and Yu. Okhlobystin, Zh. Obshch. Khim.,50, 958 (1980).

    Google Scholar 

  22. V. B. Panov M. V. Nekhoroshev, and A. A. Bjkbwe O. Yu. Okhlobystin Dokl. Acad Nauk SSSR,243, 372 (1978).

    Google Scholar 

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N. G. Chernyshevskii Saratov State University, Saratov, K. A. Fedin Saratov State Pedagogical Institute, Saratov. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1299–1319, October, 1996. Original article submmited June 8, 1995

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Kharchenko, V.G., Pchelintseva, N.V. Unsaturated 1,5-diketones and their halogen-substituted derivatives — Preparation and use in the synthesis of heterocycles. Chem Heterocycl Compd 32, 1113–1130 (1996). https://doi.org/10.1007/BF01169220

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