Studies on the syntheses of heterocyclic compounds—DXCI

A facile total synthesis of (±)-cherylline via an aziridinium intermediate

“…amine hydrochloride (1 g), sodium acetate (2 g), and ethanol (40 ml) was heated under reflux for 1 h. After evaporation of the solvent, the residue was poured into water (40 ml), and the precipitated solid was filtered off to give the oxime ( 3-BenzyZoxy-4-methoxybenzylam~~e (6).-To a stirred suspension of lithium aluminium hydride (0.6 g) in tetrahydrofuran (THF) (10 ml) was added a solution of the oxime (5) (2.54 g) in THF (50 ml) during 0.5 h. After stirring for 3 h at ambient temperature, the excess of reagent was decomposed by addition of water, and the resulting mixture was filtered through a Celite pad. The filtrate was dried (Na2S04) and evaporated to leave the residue which was purified by distillation to give the amine (6)…”

Three tetrahydroisoquinolinedione derivatives

“…Displacement ellipsoids are drawn at the 30% probability level. alkaloids such as corgoine (Kametani et al, 1975) and sendaverine (Kametani et al, 1979).…”

Secondary Benzylation Using Benzyl Alcohols Catalyzed by Lanthanoid, Scandium, and Hafnium Triflate.

“…The combined organic layer was washed once with brine (100 mL), dried over MgSO 4 , filtered, and the filtrate was concentrated to give an yellow solid (8.87g, quant. ), which was used for the next reaction S5 without further purification.O OH1-(4-Benzyloxyphenyl)ethanol (4d) 5. To a solution of 4-(Benzyloxy)acetophenone (6.540 g, 28.91 mmol) in EtOH (21 mL) and tetrahydrofuran (20 mL) was added NaBH 4 (1.093 g, 28.90 mmol) at room temperature.…”