Reactions of Carbon Dioxide with 2-Methoxyoxirane Derivatives and a-Halogenated Acylophenones in the Presence of Aliphatic Amines Formation of 2-Oxazolidinone Derivatives

Abstract

Reactions of carbon dioxide with aliphatic primary or secondary amines readily gave the corresponding ammonium carbamates in variety of solvents. The used of carbamic acids would appear to offer certain advantages to the study of the carbon dioxide incorporation into organic compounds under mild conditions.
Reactions of 2-methoxy oxiranes or a-halogenated acylophenones with carbon dioxide and aliphatic amines in methanol gave corresponding 3-alkyl-4-hydroxy-2-oxazolidinone derivatives.3-Isopropyl-4-hydroxy-5, 5-dimethy1-4-pheny1-2-oxazolidinone was thus obtained from 2-methoxy3, 3-dimethyl-2-phenyloxirane or α-bromisobutyrophenone with isopropylamine. The structure of the oxazolidinones was deduced from their IR spectra which show strong carbonyl bands at 1740 cm^-1.
Acid hydrolyse s of the oxazolidinones afforded a-hydroxyisobutyrophenone. Catalytic reduction in acidic methanol and following hydrolysis gave corresponding 1-alkylamino-1-pheny1-2propanols. The mechanism of the oxazolidinone formation is discussed.