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Reaktionen mit cyclischen Oxalylverbindungen, XXIV. Zur Reaktion von 4-Benzoyl-5-phenyl-furan-2,3-dion mit Phenylhydrazonen bzw. Phenylhydrazin

Reactions of cyclic oxalyl compounds, XXIV. Reaction of 4-benzoyl-5-phenyl-furan-2,3-dione with phenylhydrazones and phenylhydrazine

  • Organische Chemie Und Biochemie
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Abstract

4-Benzoyl-5-phenyl-furan-2,3-dione (1) reacts with various phenylhydrazones2 at 60–80°C to the pyrazole carboxylic acid3 a, which then can be decarboxylated to 4-benzoyl-1,5-diphenyl-pyrazole (5).1 and phenylhydrazine combine again yielding3 a as the main product and the isomeric pyridazinone6 as by-product. At higher temperatures (120–140°C) the reaction of1 with2 a leads to the formation of dibenzoyl acetic acid hydrazide derivatives8.

The structures of all products were confirmed by IR, MS,15N- and13C-NMR spectroscopic measurements, in the case of the pyridazinone6 also by an X-ray study.6 crystallizes with one moleDMSO monoclinically in space group P 21/n (Nr. 14) with 4 molecules6 andDMSO per cell.

The reaction pathways leading to the compounds3, 6 and8 are discussed.

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Literatur

  1. XXIII. Mitt.Kollenz G., Penn G., Ott W., Peters K., Peters E. M., Schnering H. G. v., Chem. Ber.117, 1310 (1984).

    Google Scholar 

  2. Wentrup C., Winter H. W., Gross G., Netsch K. P., Kollenz G., Ott W., Biedermann A. G., Angew. Chem.96, 791 (1984); Angew. Chem. Int. Ed. Engl.23, 802 (1984).

    Google Scholar 

  3. Ziegler E.,Kollenz G.,Ott W., Synthesis1973, 679.

  4. Ott W.,Kollenz G.,Ziegler E., Synthesis1975, 433.

  5. Eckstein Z., Urbanski T., 1,3-Oxazine-Derivatives in Adv. Heterocycl. Chem. Vol.23, p. 1 (Katritzky A. R., ed.). New York: Academic Press. 1978.

    Google Scholar 

  6. Kollenz G., Monatsh. Chem.109, 249 (1978); dort weitere Literaturhinweise.

    Google Scholar 

  7. Mecke R., in DMS-Katalog, Nr. 10053. Verlag Chemie. 1967.

  8. Auwers K. v., Mauss H., J. f. Prakt. Chem.177, 311 (1927).

    Google Scholar 

  9. Hesse M., Meier H., Zeeh B., Spektroskop. Methoden in der Org. Chemie, S. 169. Stuttgart: G. Thieme. 1984.

    Google Scholar 

  10. Martin G. J., Martin M. L., Gouesnard J. P.,15N-NMR-Spectroscopy, p. 221. Berlin-Heidelberg-New York: Springer. 1981;

    Google Scholar 

  11. Hawkes G. E.,Randall E. W.,Elugero J.,Marazine C. J., J. Chem. Soc. Perkin Trans. 21977, 1024.

  12. Auwers K. v., Schmidt W., Ber. dtsch. chem. Ges.58, 528 (1925);

    Google Scholar 

  13. Auwers K. v., Wunderling H., ibid.67, 644 (1934).

    Google Scholar 

  14. Cusmano S., Gazz. chim. ital.70, 227 (1940);

    Google Scholar 

  15. Panizzi L., ibid.73, 13 (1943).

    Google Scholar 

  16. Shapiro M. J., Kohle A. D., Org. Magn. Res.12, 235 (1979);

    Google Scholar 

  17. Shapiro M. J.,Kolpak M. X.,Lemke T. L., J. Org. Chem.1984, 187.

  18. Cucka P., Acta Cryst.16, 318 (1963).

    Google Scholar 

  19. Katritzky A. R., Physical Methods in Heterocycl. Chem., Vol. V ff. New York: Academic Press. 1972.

    Google Scholar 

  20. Kennard O., Watson D. G., Molecular Structures and Dimensions. Vol. 1–15 (1935–1983), Bibliography, University Press Cambridge, U.K.

    Google Scholar 

  21. Bayer O., in: Methoden der Org. Chemie,Houben-Weyl-Müller, Bd. VII/1, S. 474. Stuttgart: G. Thieme. 1954;

    Google Scholar 

  22. Stetter H.,, Bd. VII/2a, S. 804. Stuttgart: G. Thieme. 1973.

    Google Scholar 

  23. Maynez S. R., Pelavin L., Erker G., J. Org. Chem.40, 3302 (1975).

    Google Scholar 

  24. Lwowski W., in: Compr. Heterocycl. Chem. Vol.7, p. 475 (Katritzky A. R., Rees Ch. W., eds.). Oxford: Pergamon Press. 1984.

    Google Scholar 

  25. Khattab S. A., Shawali S. A., Farag A. M., J. Chem. Eng. Data22, 104 (1977); Chem. Abstr.86, 120940 (1977).

    Google Scholar 

  26. Seki K., Isegawa J., Fukuda M., Ohki M., Chem. Pharm. Bull.32, 1568 (1984).

    Google Scholar 

  27. Kost A. N., Grandberg I. I., in: Adv. Heterocycl. Chem. Vol.6, 369 (Katritzky A. R., ed.). New York: Academic Press. 1966.

    Google Scholar 

  28. Eiden F., Teupe E. G., Arch. Pharm.312, 863 (1979); dort weitere Literaturhinweise.

    Google Scholar 

  29. Schantl J. G., Karpellus P., Prean M., Tetrahedron38, 2643 (1982).

    Google Scholar 

  30. Abdalla M. M., Soliman E. A., Hamed A. A., Osman M. W., Egypt. J. Chem.23, 93 (1980).

    Google Scholar 

  31. Rudorf W. D., Augustin M., J. f. Prakt. Chem.323, 55 (1981).

    Google Scholar 

  32. Kurihara T., Uno T., Sakamoto Y., J. Heterocycl. Chem.17, 231 (1980).

    Google Scholar 

  33. Gelin S., Deshayes Ch., Chabannet M., J. Heterocycl. Chem.16, 1117 (1979); dort weitere Literaturhinweise.

    Google Scholar 

  34. Tisler M., Stanovnik B., in: Adv. Heterocycl. Chem. Vol.9, p. 313 (Katritzky A. R., ed.). New York: Academic Press. 1968; ibid. Vol.24, p. 426. 1979.

    Google Scholar 

  35. Naulet N., Filleux M. L., Martin G. J., Pornet J., Org. Magn. Res.7, 326 (1975).

    Google Scholar 

  36. Katritzky A. R.,Baker V. J.,Brito-Palma F. M. S., J. Chem. Soc., Perkin Trans. 21980, 1739.

  37. Jäger V.,Buß V., Liebigs Ann. Chem.1980, 101;

  38. Jäger V.,Buß V.,Schwab W., ibid.1980, 122.

  39. Ziegler E.,Kollenz G.,Ott W., Synthesis1973, 679.

  40. Staudinger H., Liebigs Ann. Chem.355, 60 (1907).

    Google Scholar 

  41. Andreichikov Y. S., Ionov Y. V., Aleksandrov B. B., Onorin A. A., USSR Pat. 810677 (7. 3. 1981) Chem. Abstr.95, 61809 (1981).

    Google Scholar 

  42. Sheldrick G. M., SHELXTL, An Integrated System for Solving, Refining and Displaying Crystal Structures from Diffraction Data. Universität Göttingen, 1983.

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Authors and Affiliations

  1. Organic Kimya Bölümü, Istanbul Universitesi, Mühendislik Fakültesi, Istanbul, Türkei

    Yunus Akcamur

  2. Institut für Organische Chemie, Universität Graz, A-8010, Graz, Österreich

    Gerhard Penn, Erich Ziegler, Heinz Sterk & Gert Kollenz

  3. Max-Planck-Institut für Festkörperforschung, D-7000, Stuttgart 80, Bundesrepublik Deutschland

    Karl Peters, Eva-Maria Peters & Hans Georg von Schnering

Authors
  1. Yunus Akcamur
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  2. Gerhard Penn
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  3. Erich Ziegler
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  4. Heinz Sterk
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  5. Gert Kollenz
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  6. Karl Peters
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  7. Eva-Maria Peters
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  8. Hans Georg von Schnering
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Akcamur, Y., Penn, G., Ziegler, E. et al. Reaktionen mit cyclischen Oxalylverbindungen, XXIV. Zur Reaktion von 4-Benzoyl-5-phenyl-furan-2,3-dion mit Phenylhydrazonen bzw. Phenylhydrazin. Monatsh Chem 117, 231–245 (1986). https://doi.org/10.1007/BF00809443

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  • DOI: https://doi.org/10.1007/BF00809443

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