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

Kumar Vinod | Zendy; Kaushik M. P. | Zendy; Mazumdar Avik | Zendy

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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)

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