Monatshefte für Chemie / Chemical Monthly

, Volume 117, Issue 11, pp 1305–1323 | Cite as

Methoden zur Darstellung von 4-Azido-2(1H)-chinolonen

  • Wolfgang Stadlbauer
Organische Chemie Und Biochemie

Methods for the synthesis of 4-azido-2(1H)-quinolones

Abstract

4-Hydroxy-2-quinolones1 are generally found to be converted to the 4-azidocompounds3via the 4-chloroquinolones2, the 4-tosyloxyquinolones6, or the 4-aminoquinolones4, respectively. Choice of the reaction conditions and yields depend on the substituent in position 3 of the quinoline nucleus. For comparison the O-analogous coumarin derivatives9 have been studied to give the 4-azidoderivatives11via the 4-chlorocoumarins10.

Keywords

4-Amino-2(1H)-quinolones 4-Azido-2(1H)-quinolones 4-Chloro-2(1H)-quinolones 4-p-Tosyloxy-2(1H)-quinolones 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literatur

  1. [1]
    Diese Arbeit ist die 3. Mitt. der Serie „Organische Azide in der Heterocyclen-Synthese“ 2. Mitt:Faber K, Kappe Th (1984) J Heterocycl Chem 21: 1881Google Scholar
  2. [2]
    Stadlbauer W, Kappe Th (1984) Monatsh Chem 115: 467Google Scholar
  3. [3]
    Stadlbauer W, Kappe Th (1982) Monatsh Chem 113: 751Google Scholar
  4. [4] a)
    Stadlbauer W, Schmut O, Kappe Th (1980) Monatsh Chem 111: 1005;Google Scholar
  5. [4] b)
    Kappe Th, Schmidt H (1972) Org Prep Proc Int 4: 233;Google Scholar
  6. [4] c)
    Kappe Th, Brandner A (1974) Z Naturforsch 29 b: 292;Google Scholar
  7. [4] d)
    Stadlbauer W, Kappe Th (1975) Z Naturforsch 30b: 139Google Scholar
  8. [5] a)
    Stadlbauer W, Ghobrial N, Kappe Th (1980) Z Naturforsch 35 b: 892;Google Scholar
  9. [5] b)
    Stadlbauer W, Kappe Th (1978) Monatsh Chem 109: 1485;Google Scholar
  10. [5] c)
    Ziegler E, Kappe Th (1965) Monatsh Chem 96: 77Google Scholar
  11. [6] a)
    Stadlbauer W, Karem AS, Kappe Th, Monatsh Chem, nachstehend;Google Scholar
  12. [6] b)
    Stadlbauer W Z Naturforsch, im DruckGoogle Scholar
  13. [7] a)
    Iddon B, Meth-Cohn O, Scriven EFV, Suschitzky H, Gallagher PT (1979) Angew Chem 91: 965; (1979) Angew Chem Int Ed 12: 900;Google Scholar
  14. [7] b)
    Suschitzky H (1983) Wiss Z Karl-Marx-Univ Leipzig, Math-Naturwiss R 32 (4): 416;Google Scholar
  15. [7] c)
    Dyall LK (1983) In: The chemistry of functional groups, Suppl D,Patai S, Rappoport Z (ed), John Wiley and Sons Ltd, ChichesterGoogle Scholar
  16. [8]
    Richardson AC (1972) In:Whistler RL, DeMiller JN (eds) Methods in carbohydrate chemistry. Academic Press, New YorkGoogle Scholar
  17. [9]
    Faber K (1981) Dissertation Univ Graz und dort zitierte LiteraturGoogle Scholar
  18. [10] a)
    Ziegler E, Wolf R, Kappe Th (1965) Monatsh Chem 96: 418;Google Scholar
  19. [10] b)
    Ziegler E, Gelfert K (1959) Monatsh Chem 90: 822Google Scholar
  20. [11]
    Gabriel S (1918) Ber Dtsch Chem Ges 51: 1500Google Scholar
  21. [12]
    Ziegler E, Salvador R, Kappe Th (1962) Monatsh Chem 94: 1376;Ziegler E, Kappe Th (1962) Monatsh Chem 94: 447Google Scholar
  22. [13]
    Friedländer P, Müller F (1887) Ber Dtsch Chem Ges 20: 2009Google Scholar
  23. [14]
    Karem AS (1984) Diplomarbeit, Universität GrazGoogle Scholar
  24. [15]
    Stadlbauer W, Kappe Th (1981) Synthesis 1981: 833Google Scholar
  25. [16]
    Schroeder HE, Rigby GW (1941) J Amer Chem Soc 71: 2205;Hashimoto T, Nagase S (1960) Yakugaku Zasshi 80: 1806; (1961) Chem Abstr 55: 9401Google Scholar
  26. [17]
    Buchmann FJ, Hamilton CS (1942) J Amer Chem Soc 64: 1352Google Scholar
  27. [18]
    Peinhardt G, Reppel L (1979) Pharmazie 25: 60Google Scholar
  28. [19]
    Tabacovic K, Tabacovic I, Trkovnik M, Trinajstic N (1983) Liebigs Ann Chem 1983: 1901Google Scholar
  29. [20]
    Wolfbeis OS, Uray G (1978) Monatsh Chem 109: 123Google Scholar
  30. [21]
    Savel'ev VL, Artamonova OS, Trockaya VS, Vinokurov VG, Zagorevskii VA (1973) Khim Geterotsikl Soedin 1973: 885Google Scholar
  31. [22]
    Ahluwalia VK, Prakash C, Jolly RS (1979) Gazz Chim Ital 109: 641;Google Scholar
  32. [22] b)
    Zagorevskii VA (1960) Zhur Obshch Khim 30: 1378Google Scholar
  33. [23]
    Still WC, Kahn M, Mitra A (1978) J Org Chem 43: 2923Google Scholar

Copyright information

© Springer-Verlag 1986

Authors and Affiliations

  • Wolfgang Stadlbauer
    • 1
  1. 1.Institut für Organische ChemieKarl-Franzens-Universität GrazGrazÖsterreich

Personalised recommendations