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Reactions with pyrrolidine-2,4-diones, I. New synthesis of pyrano[2,3-c]pyrrole and pyrrolo[3,4-b]pyridine systems

Reaktionen mit Pyrrolidin-2,4-dionen, I. Eine neue Synthese von Pyrano[2,3-c]pyrrol- und Pyrrolo[3,4-b]pyridin-Systemen

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

The synthesis of some substituted 4-hydroxy-2,5,6,7-tetrahydro-pyrano[2,3-c]pyrrole-2,5-diones (5) and 4-hydroxy-1,2,6,7-tetrahydro-5H-pyrrolo[3,4-b]pyridine-2,5-diones (6) by reacting 1,5-diaryl-pyrrolidine-2,4-diones (1) and 1,5-diaryl-1,5-dihydro-4-amino-2H-pyrrol-2-ones (3) with bis-2,4,6-trichlorophenyl malonates (4) is described.

Zusammenfassung

Die Synthese einiger substituierter 4-Hydroxy-2,5,6,7-tetrahydro-pyrano[2,3-c]pyrrol-2,5-dione (5) und 4-Hydroxy-1,2,6,7-tetrahydro-5H-pyrrolo[3,4-b]pyridin-2,5-dione (6) gelingt durch Reaktion von 1,5-Diaryl-pyrrolidin-2,4-dion (1) bzw. 1,5-diaryl-1,5-dihydro-4-amino-2H-pyrrol-2-on (3) mit Malonsäure-bis-2,4,6-trichlorphenylester (4).

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References

  1. Soliman F. S. G., Pharmazie32, 572 (1977).

    Google Scholar 

  2. Soliman F. S. G.,Kassem M. G., 8th International Congress of Heterocyclic Chemistry, Graz, Austria, August 1981; Abstr. p. 423.

  3. Ziegler E., Chimia24,62 (1970).

    Google Scholar 

  4. Kumashiro I., Nippon Kagaku Zasshi82, 932 (1961); C. A.57, 12413e (1962).

    Google Scholar 

  5. Baues M., Kraatz U., Korte F., Chem. Ber.105, 1345 (1972).

    Google Scholar 

  6. American Cyanamid Co. (byLos M., Walworth B. L.), US.-Pat. 4,164,404 (1979); C.A.91, 193319 w (1979).

  7. Farley C. P., Eliel E. L., J. Amer. Chem. Soc.78, 3477 (1956).

    Google Scholar 

  8. Oakes V.,Rydon H. N., J. Chem. Soc.1956, 433.

  9. Barnes R. A., Godfrey J. C., J. Org. Chem.22, 1043 (1957).

    Google Scholar 

  10. Anchor Chemical Co. Ltd. (byOakes V.,Ryden H. N.), US.-Pat. 2,924,599 (1960); C. A.54, 9964 a (1960).

  11. Armarego W. L. F.,Milloy B. A.,Sharma S. C., J. Chem. Soc. Perkin Trans. I,1972, 2485.

  12. Rice L. M., Grogan C. H., Reid E. E., J. Amer. Chem. Soc.75, 4911 (1953).

    Google Scholar 

  13. Jindra A., Chem. Listy41, 221 (1947); C. A.47, 4339 b (1953).

    Google Scholar 

  14. Carboni S., Berti G., Gazz. Chim. Ital.84, 683 (1954).

    Google Scholar 

  15. Augustin M., Koehler M., Harzer R., Bernhard G., Brigsne H., Wiss. Z. Martin-Luther Univ. Halle-Wittenberg, Math.-Naturwiss. Reihe21, 137 (1972); C. A.77, 75188 r (1972).

    Google Scholar 

  16. Rhone-Poulenc S. A. (byChallier J. L.,Jeanmart C.,Messer M. N.), Ger. Offen. 2,251, 559 (1973); C. A.79, 32100 e (1973).

  17. Ciba-Geigy Corp. (byGschwend H. W.,Hillman M. J.), US.-Pat. 4,025,505 (1977); C. A.87, 102074 r (1977).

  18. Hurst J.,Wibberly D. G., J. Chem. Soc.1962, 119.

  19. Sato Y., Iwashige T., Chem. Pharm. Bull.8, 427 (1960).

    Google Scholar 

  20. Sankyo Co., Ltd. (bySato Y.,Iwashige T.,Miyadera), Japan Pat. 21,543 (61) (1959); C. A.57, 13757 h (1962).

    Google Scholar 

  21. Sankyo Co., Ltd. (bySato Y.,Iwashige T.,Miyadera T.,Nishimura T.), Japan Pat. 7346 (63) (1959); C. A.59, 11514 a (1963).

  22. Vollmann J. W. H., Bredereck K., Bredereck H., Chem. Ber.105, 2933 (1972).

    Google Scholar 

  23. Zukauskaite L.,Stankevicius A.,Kost A. N., Khim. Geterotsikl. Soedin.1978, 63; C. A.88, 170005 q (1978).

  24. Madhav R., Z. Naturforsch.29 b, 453 (1974).

    Google Scholar 

  25. Gruppo Lepetit S. p. A. (byTarzia G.,Panzone G.), Ger. Offen. 2,511,585 (1975); C.A.84, 4933 p (1976).

  26. Tarzia G., Panzone G., Carminati P., Schiatti P., Selva D., Farmaco, Ed. Sci.31, 81 (1976); C. A.85, 21271 j (1976).

    Google Scholar 

  27. Madhav R., J. Chem. Soc. Perkin Trans. I,1974, 2108.

  28. Sankyo Co., Ltd. (bySato Y.,Shimoji Y.,Kumakura S.,Takagi H.), Japan Pat. 77, 153,995 (1977); C. A.88, 170127 f (1978).

    Google Scholar 

  29. Sato Y., Shimoji Y., Fujita H., Mizumo H., Kumakura S., Yakugaku Zasshi98, 448 (1978); C. A.89, 59846 w (1978).

    Google Scholar 

  30. Sammour A., Selim M. I. B., Nour Eldeen M. M., U. A. R. J. Chem.14, 371 (1971).

    Google Scholar 

  31. Baydar A. E.,Boyd G. V., J. Chem. Soc. Chem. Commun.1979, 178.

  32. Rhone-Poulenc S. A. (byCotrel C.,Crisan C.,Jeanmart C.,Leger A.), Ger. Offen. 2,516,057 (1976); C. A.86, 43743 n (1977).

  33. Benger Laboratories Ltd. (byHunter W. Y.,King J.,Millard B. J.), Brit. Pat. 1,086,637 (1967); C. A.68, 95695 w (1968).

  34. Kappe Th., Mh. Chem.98, 874 (1967).

    Google Scholar 

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, A. R. Egypt

    Farid S. G. Soliman

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

    Thomas Kappe

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  1. Farid S. G. Soliman
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  2. Thomas Kappe
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Dedicated to Prof. Dr. Dr. h. c.O. Kratky, Graz, on the occasion of his 80th birthday.

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Soliman, F.S.G., Kappe, T. Reactions with pyrrolidine-2,4-diones, I. New synthesis of pyrano[2,3-c]pyrrole and pyrrolo[3,4-b]pyridine systems. Monatsh Chem 113, 475–484 (1982). https://doi.org/10.1007/BF00799923

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  • DOI: https://doi.org/10.1007/BF00799923

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