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

Article abstract of DOI:10.1007/BF00798958

The reaction of 2-picolylketones (1a, b) with reactive trichlorophenyl malonates (2a-f) leads to 1-acyl-2-hydroxy-4-quinolizinones (3a-i) which can be easily deacylated by boiling hydrochloric acid yielding 4-quinolizinones 4a-f.The 3-acetyl-2-hydroxy-4-quinolizinones 6 and 8 are obtained by Klosa-Ziegler acylation of 4a and 7, respectively.The reaction of the acetyl compound 3a with acetic anhydride yields the 2-pyrone derivative 9, whereas the propionyl derivative 3g yields the 4-pyrone 10 under the same conditions.Nitration of 3e does not give the 1-nitro derivative 12 but rather the 1,3-dinitro compound 11. - Keywords: 3-Acetyl-2-hydroxy-4-quinolizinones; 1-Acyl-2-hydroxy-4-quinolizinones; Bis-2,4,6-trichlorophenyl malonates; Deacylation; Klosa-Ziegler-acylation