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An Efficient Approach for the Synthesis of N‐1 Substituted Hydantoins
Author(s) -
Kumar Vinod,
Kaushik M. P.,
Mazumdar Avik
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200701025
Subject(s) - chemistry , sodium hydride , alkyl , aryl , cyanogen bromide , tetrahydrofuran , organic chemistry , hydrolysis , hydride , bromide , medicinal chemistry , primary (astronomy) , ethyl bromoacetate , halide , combinatorial chemistry , hydrogen , biochemistry , physics , astronomy , solvent , peptide sequence , gene
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)