The Journal of Organic Chemistry

Open-Chain Reissert Compounds: One-Pot Synthesis and Utility in Synthesis of Unsymmetrical Imides,. alpha.-Acylamino Carboxamides, Imidazolinones, and …

JP Leblanc, HW Gibson

Index: Leblanc, Jean-Pierre; Gibson, Harry W. Journal of Organic Chemistry, 1994 , vol. 59, # 5 p. 1072 - 1077

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Citation Number: 21

Abstract

Acyclic Reissert compounds 2 and bis (Reissert compound) s 3-5 can be conveniently prepared in a biphasic system without isolation of the intermediate a-amino nitriles. Treatment of 2 with sodium hydride affords substituted unsymmetrical imides such as 8. Oxidative hydrolysis of 2 by hydrogen peroxide converts the nitrile groups to primary amides, giving acyl derivatives of a-amino carboxamides 9, whereas substituted analogs 7 ...