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A novel benzo[a]quinolizidine rearrangement involving intramolecular carbamyl-chloride-induced cleavage of a tertiary amine
Authors:Bruce E Maryanoff  Albert J Molinari  Gary P Wooden  RA Olofson
Institution:Research Division, McNeil Pharmaceutical Spring House, Pennsylvania 19477 USA;Department of Chemistry, The Pennsylvania State University University Park, Pennsylvania 16802 USA
Abstract:The free base of benzoquinolizidine 3 undergoes a facile rearrangement to pyrimidoisoquinoline 4, the structure of which was confirmed by x-ray crystallography.The regiospecificity of this novel rearrangement is governed by stereoelectronic factors.
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