Kinetics and mechanism of base-catalyzed cyclization of substituted amides and nitriles of hydantoic acid

V Macháček, G Svobodová…

Index: Machacek, Vladimir; Svobodova, Gabriela; Sterba, Vojeslav Collection of Czechoslovak Chemical Communications, 1987 , vol. 52, # 1 p. 140 - 155

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Citation Number: 3

Abstract

Abstract Rates of base-catalyzed cyclizations of 8 substituted derivatives of hydantoic acid amide type R 3-NH (5)-CO (4)-NR 2 (3)-CH 2 (2)-CO (1)-NHR 1 and 9 nitriles type R 3-NH (5)-CO (4)-NR 2 (3)-CHR 1 (2)-CN have been measured in aqueous and methanolic media. The cyclization of the amides in aqueous medium is also accompanied by hydrolysis of the hydantoins formed. In some cases the hydrolysis rate constant is greater than the ...