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A Quinolizine to Indolizine Transformation

Treatment of quinolizinium bromide with two equivalents of piperidine gives a high yield of a product A, C14H18N2. Reaction of A with phenacyl bromide followed by quenching of the reaction mixture with water gives a product B which was originally claimed to be 3-benzoyl-2-vinylindolizine. Subsequent reinvestigation of the structure of B, however, showed that it was in fact 3-(2-phenyl-l-indolizinyl)prop-2-ene-l-al 1. [Pg.103]

Deduce the structure of A and give a reasonable explanation for the conversion of A into B (si). [Pg.103]

SftHetAr Reactions Often Proceed with Complications [Pg.104]

Treatment of 2-bromo-6-phenoxypyridine with potassium amide in liquid ammonia gave a mixture of three isomeric compounds which were identified as 2-amino-6-phenoxypyridine (28%), 4-amino-2-phenoxypyridine (9%), and 2-methyl-4-phenoxypyrimidine (50%). [Pg.104]

Suggest mechanisms for the formation of these three products. [Pg.104]


See other pages where A Quinolizine to Indolizine Transformation is mentioned: [Pg.103]   


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