ISSN:
1434-4475
Keywords:
3-Acetyl-2-hydroxy-4-quinolizinones
;
1-Acyl-2-hydroxy-4-quinolizinones
;
Bis-2,4,6-trichlorophenyl malonates
;
Deacylation
;
Klosa-Ziegler-acylation
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00798958
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