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Synthesis of some schiff bases of 3-aroyl-6-aryl-4-hydroxy-2H-pyran-2-ones

Synthese von Schiff'schen Basen von 3-Aroyl-6-aryl-4-hydroxy-2H-pyran-2-onen

  • Organische Chemie Und Biochemie
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Summary

The reaction of 3-aroyl-6-aryl-4-hydroxy-2H-pyran-2-ones (Ar=p-tolyl, 1,1′-biphenyl-4-yl or thienyl) with aniline and substitutedo-phenylenediamine (R=H, CH3 or Cl) yields a series of new Schiff bases2a–f in 51–72% yield. Bromination of1a gave the 5-bromo derivative1c, while the compounds1a,1b,2b,2e, and2f were converted into 2,6-diaryl-4H-pyran-4-ones3a–c. All products have been fully characterized.

Zusammenfassung

Die Reaktion von 3-Aroyl-6-aryl-4-hydroxy-2H-pyran-2-onen (Ar=p-Tolyl, 1,1′-Biphenyl-4-yl oder Thienyl) mit Anilin und substituierteno-Phenylendiaminen liefert neue Schiff'sche Basen2a–f/bd in 51–72% Ausbeute. Bromierung von1a gab das 5-Bromderivate1c, während die Verbindungen1a,1b,2b,2e und2f in 2,6-Diaryl-4H-pyran-4-onen3a–c übergeführt wurden. Alle Produkte wurden voll charakterisiert.

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References

  1. Duraković S., Sušnik-Rybarski I., Vorkapić-Furač J., Mihelić F., Lasinger J. (1986) Hrana i Ishrana3: 165

    Google Scholar 

  2. Tkalčević K., Duraković S., Sušnik-Rybarski I., Duraković Z., Pospišil O., Radić B., Brečević Lj. (1987) Arh. hig. rada toksikol.38: 299

    Google Scholar 

  3. Duraković S., Sušnik I., Galić J., Rajnović P., Markov K., Pospišl O., Štilinović L. (1989) Mikrobiologija26: 1

    Google Scholar 

  4. Balenović K. (1948) Rec. Trav. Chim. Pays-Bas67: 282

    Google Scholar 

  5. Laćan M., Sušnik-Rybarski I., Mesić E., Džanić H. (1980) Liebigs Ann. Chem. 681

  6. Elderfield R. C., Mayer V. B. (1954) J. Am. Chem. Soc.76: 1883

    Google Scholar 

  7. Sušnik-Rybarski I., Filipović-Marinić N., Baturić D., Laćan M. (1983) Bull. Soc. Chim. Beograd48: 489

    Google Scholar 

  8. Poje M., Gašpert B., Balenović K. (1978) Rec. Trav. Chim. Pays-Bas97: 242 and references cited therein

    Google Scholar 

  9. Laćan M., Sušnik-Rybarski I., Koprivanac S., Ciprić N., Nekola N., Deželić-Šuflaj L. (1966) II Jug. kongres za čistu i primjenjenu hemiju, 16–19 Juna, Beograd, 58

  10. Andreičikov Ju. S., Nahinova Ju. A., Kozlov A. P., Rusakov I. A. (1978) Zh. Org. Khim.14: 2436 (synthesized the1 a by decarbonylation of 5-arylfuran-2,3-dione)

    Google Scholar 

  11. Marjanović V. B. (1954) Sc Thesis, Faculty of Technology University of Zagreb

  12. Smitherman H. C., Ferguson L. N. (1968) Tetrahedron24: 923 (synthesized the3 a from triketone in conc. H2SO4)

    Google Scholar 

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Sušnik, I., Vorkapić-Furač, J., Duraković, S. et al. Synthesis of some schiff bases of 3-aroyl-6-aryl-4-hydroxy-2H-pyran-2-ones. Monatsh Chem 123, 817–822 (1992). https://doi.org/10.1007/BF00812331

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  • DOI: https://doi.org/10.1007/BF00812331

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