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Paper | Regular issue | Vol 27, No. 3, 1988, pp.713-718
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4392
Studies on Reactive Intermediates. Part VI. Synthesis of Benzo[a]quinolizines via Methylketene Dimer

Mohsen Daneshtalab,* Ronald G. Micetich, and Sedighe Forghanifar

*SynPhar Laboratories Inc., 4290-91A Street, Edmonton, Alberta, T6E 5V2, Canada


Reaction of methylketene dimer with isoquinoline in neat condition or refluxing ether resulted in the formation of 2-hydroxy-1,3-dimethyl-4-oxo-4H-benzo[a]quinolizine (VIII) in 55% yield. The reaction in acetic acid gave rise to 2-acetoxy-1,3-dimethyl-4-oxo-1,4-dihydro-11HBH-benzo[a]quinolizine (VI) and 2-acetoxy-1,3-dimethyl-4-oxo-4H-benzo[a]quinoIizine (VII) in 40% and 45% yields, respectively. Compound VI has been reported as one of the precursors of emetine type alkaloids.