Synthesis and biological activity of 1-(aryloxy)-3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-2-yl)propan-2-ols

Treatment of 1-(4-chlorobenzylamino)-2-methylpropan-2-ol with concentrated sulfuric acid at 0°C gave 6-chloro-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline which reacted with (aryloxymethyl)oxiranes to afford new propan-2-ol derivatives of the tetrahydroisoquinoline series, 1-(aryloxy)-3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydroisoquinolin-2-yl)propan-2-ols. Some of the synthesized compounds or their hydrochlorides showed moderate adrenergic blocking and sympatholytic activities.     

Synthesis, structure, and properties of piperidinium 3-(4-chlorophenyl)-2-cyano-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)thiopropionimidate

Condensation of 4-chlorobenzaldehyde with cyanothioacetamide and dimedone in the presence of piperidine afforded piperidinium 3-(4-chlorophenyl)-2-cyano-3-(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)thiopropionimidate. This salt was studied by X-ray diffraction analysis and used in the synthesis of the previously unknown partially hydrogenated 2-alkylthioquinolin-2-ones. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 733–737, April, 2000.     

Photochemistry of 6-trifluoromethyl-4,4-dimethyl-2-cyclohexenone

The photochemical behaviour of the title compound, newly synthesized in four steps from 4,4-dimethylcyclohexanone, is compared to that of 4,4-dimethyl- and 4,4,6-trimethyl-2-cyclohexenone. All three enones undergo rearrangement to bicyclo[3.1.0]hexan-2-ones and 3-isopropyl-2-cyclopentenones in benzene, t.butanol and acentonitrile, but only the CF₃-enone is also reduced to the saturated ketone in the latter two solvents.