caa a22 4500 469038624 CHVBK 20180323132803.0 cr unu---uuuuu 170328e19920601xx s 000 0 eng 10.1007/BF00816857 doi (NATIONALLICENCE)springer-10.1007/BF00816857 Halogenation reactions in position 3 of quinoline-2,4-dione systems by electrophilic substitution and halogen exchange [Elektronische Daten] [Wolfgang Stadlbauer, Rita Laschober, Herbert Lutschouig, Gerda Schindler, Thomas Kappe] Halogenierungsreaktionen an der 3-Position von Chinolin-2,4-dion-systemen durch elektrophile Substitution und Halogenaustausch 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. Springer-Verlag, 1992 Fluorination nationallicence 4-Hydroxy-2(1 H )-quinolones, 3-alkyl/3-aryl/3-fluoro nationallicence 1-Hydroxy-benzo[ij] quinolizine-3-ones, 2-alkyl/3-aryl nationallicence Quinoline-2,4(1 H , 3 H )-diones, 3-azido-3-alkyl/3aryl, 3-bromo-3-alkyl/3-aryl, 3-chloro-3-alkyl/3-aryl, 3-fluoro-3-alkyl/3-aryl, 3-dichloromethyl-3-alkyl/3-aryl, 3-chloro-3-fluoro nationallicence Stadlbauer Wolfgang Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut Laschober Rita Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut Lutschouig Herbert Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut Schindler Gerda Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut Kappe Thomas Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/6-7(1992-06-01), 617-636 0026-9247 123:6-7<617 1992 123 706 https://doi.org/10.1007/BF00816857 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00816857 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Stadlbauer Wolfgang Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut NATIONALLICENCE 700 1- Laschober Rita Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut NATIONALLICENCE 700 1- Lutschouig Herbert Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut NATIONALLICENCE 700 1- Schindler Gerda Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut NATIONALLICENCE 700 1- Kappe Thomas Institute of Organic Chemistry, Department of Organic Synthesis, Karl-Franzens-University Graz, Austria aut NATIONALLICENCE 773 0- Monatshefte für Chemie / Chemical Monthly Springer-Verlag 123/6-7(1992-06-01), 617-636 0026-9247 123:6-7<617 1992 123 706 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer