Kinetics and Mechanism of the Acid-Base Equilibrium of Benzodiazeinooxazoles : Oxazolam Analogs

概要

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Oxazolidine ring-opening and ring-closing reactions of oxazolan analogs were investigated kinetically by a pH-jump method in order to elucidate the detailed reaction mechanism focusing on cis and trans isomers. Seven compounds having substituents (methyl, ethyl or phenyl group) at the 2-and 11b-positions were synthesized ahd examined. Coupled (parallel) reversible reactions due to the isomers were confirmed by analog computer analysis. The ring-opening and ring-closing reactions due to the cis isomer are both faster than those due to the trans isomer, although in the alkaline region, the ring-closing reaction due th the trans isomer could not be followed spectrophotometrically. The reason for the rate differences between the cis and trans isomers and the effects of the substituents on the intrinsic rate constants for the ring-opening and ring-closing reactions are discussed.
公益社団法人日本薬学会の論文
1988-02-25