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Halogenation reactions in position 3 of quinoline-2,4-dione systems by electrophilic substitution and halogen exchange

Halogenierungsreaktionen an der 3-Position von Chinolin-2,4-dion-systemen durch elektrophile Substitution und Halogenaustausch

  • Organische Chemie Und Biochemie
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Summary

3-Substituted 4-hydroxy-2(1H)-quinolones3,5,7 are halogenated with bromine or sulfuryl chloride to yield the quinolinediones9 or10. Reaction of3,5,7 with chloroform gives the dichloromethyl quinolinediones11. Halogen exchange leads from the chloro quinolinediones10 to fluoro quinolinedones12 and to azido quinolinediones13. Similarly the dichloro quinolinedione10 an reacts to the difluoro quinolinedione14, which is reduced to the 3-fluoro-4-hydroxyquinolone16 and reacts again with sulfuryl chloride to give the mixed 3-chloro-3-fluoroquinolinedione15.

Zusammenfassung

3-Substituierte 4-Hydroxy-2-chinolone3,5,7 reagieren mit elementarem Brom oder Sulfurylchlorid zu den 3-Halogen-chinolindionen9 oder10. Mit Chloroform reagieren die Hydroxychinolone3,5,7 zu den 3-Dichlormethylchinolondionen11. Halogenaustausch an10 führt zu den 3-Fluorchinolindionen12 und zu 3-Azidochinolindionen13. Ähnlich reagiert 3,3-Dichlorochinolindion10 an zu 3,3-Fluorchinolindion14, das zum 3-Fluor-4-hydroxychinolon16 reduziert werden kann und in weiterer Folge mit Sulfurylchlorid zum gemischten 3-Chlor-3-fluor-chinolindion15 reagiert.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria

    Wolfgang Stadlbauer, Rita Laschober, Herbert Lutschouig, Gerda Schindler & Thomas Kappe

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  1. Wolfgang Stadlbauer
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  2. Rita Laschober
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  3. Herbert Lutschouig
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  4. Gerda Schindler
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  5. Thomas Kappe
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Herrn Prof. Dr. Erich Ziegler in freundschaftlicher Verbundenheit zum 80. Geburtstag gewidmet.

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Stadlbauer, W., Laschober, R., Lutschouig, H. et al. Halogenation reactions in position 3 of quinoline-2,4-dione systems by electrophilic substitution and halogen exchange. Monatsh Chem 123, 617–636 (1992). https://doi.org/10.1007/BF00816857

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  • DOI: https://doi.org/10.1007/BF00816857

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