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Monatshefte für Chemie / Chemical Monthly

, Volume 114, Issue 4, pp 485–493 | Cite as

Chinolizine und Indolizine, XIV Umlagerungen von Heterocyclen, X Ringumwandlungen von 1-Acyl-2-hydroxy-4-chinolizinonen

  • Thomas Kappe
  • Yendra Linnau
Organische Chemie Und Biochemie

Quinolizines and indolizines, XIV. Rearrangement reactions of heterocycles, X. Ringtransformations of 1-acyl-2-hydroxy-4-quinolizinones

Abstract

By heating with ammonia or aniline 1-acyl-2-hydroxy-4-quinolizinones (1 a–e) are transformed to 4-hydroxy-5-(2-pyridyl)-2-pyridones (3 a–f), with4 a–d as minor sideproducts. The structure of the rearranged compound3 f was established by an independent synthesis starting with6 and7. The reaction of1 a, d with ethyl β-aminocrotonate (β-ACE) yields pyrono-quinolizinones8 a, b and pyronopyridones9 a, b as byproducts; the latter are obtained in high yield by reaction of3 a, b with β-ACE. The ringtransformation reaction cannot be extended to 1-methoxycarbonyl-quinolizinones, such as10; in this case 2-amino-4-quinolizinone11 is the main product of the reaction with ammonia.

Keywords

Ethyl β-aminocrotonate 4-Hydroxy-2-pyridones 2-Pyrones 

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Literatur

  1. 1.
    XIII. Mitteilung:Kappe Th., Linnau Y., Monatsh. Chem.114, 349 (1983).Google Scholar
  2. 2.
    IX. Mitteilung:Kappe Th., Ravai Y., Stadlbauer W., Monatsh. Chem.114, 227 (1983).Google Scholar
  3. 3.
    Kappe Th., Linnau Y., Liebigs Ann. Chem.761, 25 (1972).Google Scholar
  4. 4.
    Kappe Th., Monatsh. Chem.98, 874 (1967).Google Scholar
  5. 5.
    Henecka H., Chemie der β-Dicarbonylverbindungen, S. 135. Berlin-Göttingen-Heidelberg: Springer. 1950.Google Scholar
  6. 6.
    Ziegler E., Kleineberg G., Monatsh. Chem.96, 1360 (1965);Ziegler E., Belegratis K., Monatsh. Chem.98, 219 u. 221 (1967);Kappe Th., Chirazi M. A. A., Stelzel P., Ziegler E., Monatsh. Chem.103, 586 (1972).Google Scholar
  7. 7.
    Kappe Th., Baxevanidis G., Ziegler E., Monatsh. Chem.102, 1392 (1971); näheres über diese Variante derPechmann-Kondensation siehe bei:Kappe Th., Mayer C., Synthesis1981, 524.Google Scholar
  8. 8.
    Thyagarajan B. S., Gopalakrishnan P. V., Tetrahedron23, 3851 (1967).Google Scholar
  9. 9.
    Zur Aminierung von ähnlichen Systemen vgl.:Stadlbauer W.,Kappe Th., Synthesis1981, 833 (1981); Monatsh. Chem.113, 751 (1982) und dort zit. Lit.Google Scholar

Copyright information

© Springer-Verlag 1983

Authors and Affiliations

  • Thomas Kappe
    • 1
  • Yendra Linnau
    • 1
  1. 1.Abteilung für Organische Synthese, Institut für Organische ChemieKarl-Franzens-UniversitätGrazÖsterreich

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