Synthesis of 2-N,N-dialkylamino-1-aroyloxybenzocycloalkanes.

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Aroyl esters of 2-N, N-dialkylamino-1-benzocycloalkanols (6, 7), which may be considered to be semi-rigid cyclic analogs of procaine, were prepared to study the influence of the stereochemical relationship between the aroyloxy and the amino group on local anesthetic activity. The cis-compounds (6a-1, 6c-1) were more active than the corresponding trans-isomers (6b-1, 6d-1). Similarly, the optical isomers of cis-2-N, N-dimethylamino-1-benzoyloxy-1, 2, 3, 4-tetrahydronaphthalene (6c-1) differed in their activity with the l-isomer being more active. The reaction of 2-bromo-1-tetralol (9) with dimethylamine was also discussed.

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