Abstract
It is shown that the rearrangement of phenylacetic acid hydrazides obtained from 8-substituted N-amino-1,2,3,4-tetrahydroquinolines under the influence of PCl5 proceeds through a step involving the formation of a cyclohexadienoneimine derivative (which was isolated and characterized), which is formed by attack on the 10 position of the tetrahydroquinoline ring. A subsequent 1,3-sigmatropic shift of the cyanobenzyl group leads to nitriles of [6-(8-R-1,2,3,4-tetrahydroquinolyl)]phenylacetic acids. The possibility of their formation through another cyclohexadienoneimine intermediate (formed as a result of attack at the 8 position) is assumed. The nature and pathways for the formation of the side products in the rearrangement were ascertained.
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