Stereochemistry of nitrogen heterocycles. 48. Synthesis, configurations, and ir spectra of 1,2-dimethyldecahydroquinoline-5-ol isomers and their acetates

Autor: Litvinenko, G. S., Kuz'mina, N. Yu., Sokolov, D. V.
Zdroj: Chemistry of Heterocyclic Compounds; March 1984, Vol. 20 Issue: 3 p309-314, 6p
Abstrakt: Three isomers of 1,2-dimethyldecahydroquinolin-5-ol and their acetates with cis and trans fusion of the rings and different orientations of the hydroxy and acyloxy groups were obtained. The correlation of the frequencies of the C-O, O-H, and N+-H stretching vibrations with the configurations of these compounds was studied. The 1,2-dimethyl-cis-decahydroquinolin-5-ol isomer with a syn orientation of the amino and hydroxy groups exists in a conformation with an intramolecular hydrogen bond, the character of which is determined by the functional state of the amino group (OH...N in the base and N+-H...O in the hydrochloride). The hydrochloride of the acetate of this alcohol does not form an intramolecular N+-H...O(COCH3) bond.
Databáze: Supplemental Index