An Efficient Approach for the Synthesis of N‐1 Substituted Hydantoins

Abstract

Abstract An efficient three‐step route for the synthesis of N ‐ 1 alkyl/aryl‐substituted hydantoins was developed from inexpensive commercially available substrates. The reaction of amines with cyanogen bromide takes place to give monoalkyl/aryl cyanamides. This on treatment with methyl bromoacetate in the presence of sodium hydride in tetrahydrofuran affords methyl N ‐cyano‐ N ‐alkyl/arylaminoacetate, which undergoes hydrolysis and cyclization in the presence of 50 % H 2 SO 4 to afford N ‐ 1 substituted hydantoins in very good‐to‐excellent yields. Wide varieties of final products having primary, secondary, tertiary, and aryl substituents at the N ‐ 1 position were successfully synthesized by this method. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)