Synlett 2017; 28(17): 2285-2290
DOI: 10.1055/s-0036-1588468
letter
© Georg Thieme Verlag Stuttgart · New York

Facile One-Pot Synthesis of Substituted Hydantoins from Carbamates

Dinesh Kumar Tanwar, Anjali Ratan, Manjinder Singh Gill*
  • Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research (NIPER), S.A.S. Nagar, Punjab-160062, India   Email: msingh@niper.ac.in
Further Information

Publication History

Received: 13 April 2017

Accepted after revision: 21 May 2017

Publication Date:
03 August 2017 (eFirst)

Abstract

A novel and simple approach for the preparation of 3-substituted, 5-substituted, or 3,5-disubstituted hydantoins is reported. It involves the reaction of α-amino methyl ester hydrochlorides with carbamates to yield the corresponding ureido derivatives, which subsequently cyclize under basic conditions to produce substituted ­hydantoins in good yields. By applying this method, the bioactive anticonvulsant drug ethotoin was synthesized in good yield. The process avoids conventional multistep protocols and does not use the hazardous, irritant, toxic, or moisture-sensitive reagents, such as isocyanates or chloroformates, that are commonly used for the synthesis of these important compounds.

Supporting Information