Synthesis of alpha-aminomethyl derivatives of beta-phenyltetrahydrofuran-2-one.
beta-Phenyltetrahydrofuran-2-one-alpha-carboxylic acid 1 was transformed in the Mannich reaction into alpha-aminomethyl derivatives of beta-phenyltetrahydrofuran-2-one 2-6. The obtained alpha-aminomethyllactones, in reaction of ammono- and hydrazinolysis yield alpha-aminomethyl-beta-phenyl gamma-hydroxybutyric acid derivatives 7-12. Compounds 4, 5, 8, 9, and 10 depress the central nervous system, and compound 12 shows analgesic properties.
D000818:Animals; D002492:Central Nervous System Depressants / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D007928:Lethal Dose 50; D008744:Methylamines / Q000138:chemical synthesis* / Q000494:pharmacology; D051381:Rats
D002492:Central Nervous System Depressants; D005663:Furans; D008744:Methylamines