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Chinolizine und Indolizine, XIII. Acyl-2-hydroxy-4-chinolizinone

Quinolizines and indolizines, XIII. Acyl-2-hydroxy-4-quinolizinones

  • Organische Chemie Und Biochemie
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Abstract

The reaction of 2-picolylketones (1 a, b) with reactive trichlorophenyl malonates (2 a–f) leads to 1-acyl-2-hydroxy-4-quinoliziones (3 a–i) which can be easily deacylated by boiling hydrochloric acid yielding 4-quinolizinones4 a–f. The 3-acetyl-2-hydroxy-4-quinolizinones6 and8 are obtained byKlosa-Ziegler acylation of4 a and7, respectively. The reaction of the acetyl compound3 a with acetic anhydride yields the 2-pyrone derivative9, whereas the propionyl derivative3 g yields the 4-pyrone10 under the same conditions. Nitration of3 e does not give the 1-nitro derivative12 but rather the 1,3-dinitro compound11.

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Authors and Affiliations

  1. Abteilung für Organische Synthese, Institut für Organische Chemie, Karl Franzens-Universität, A-8010, Graz, Österreich

    Thomas Kappe & Yendra Linnau

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  1. Thomas Kappe
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  2. Yendra Linnau
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Kappe, T., Linnau, Y. Chinolizine und Indolizine, XIII. Acyl-2-hydroxy-4-chinolizinone. Monatsh Chem 114, 349–358 (1983). https://doi.org/10.1007/BF00798958

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  • DOI: https://doi.org/10.1007/BF00798958

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