Organic Chemistry Portal

Abstracts

Search:

Three-Component, One-Pot Sequential Synthesis of 1,3-Disubstituted 5-Arylhydantoins

Francesca Olimpieri, Alessandro Volonterio*, Matteo Zanda

*Dipartimento di Chimica, Materiali e Ingegneria Chimica ‘Giulio Natta', Politecnico di Milano, Via Mancinelli 7, 20131 Milano, Italy, Email: alessandro.volonteriopolimi.it

F. Olimpieri, A. Volonterio, M. Zanda, Synlett, 2008, 3016-3020.

DOI: 10.1055/s-0028-1087352


Abstract

Reaction of carbodiimides with α-Br(Cl)-aryl acetic acids produces N,N′-substituted 5-arylhydantoins under very mild conditions and high yields. When the carbodiimides are generated in situ by Staudinger reaction, the process becomes a one-pot, three-component sequential synthesis of libraries of differently substituted 5-arylhydantoins.

Some carbodiimides afford a mixture of hydantoin and N-acyl urea. However, in situ addition of a 2 M aqueous NaOH solution promotes the cyclization of the N-acyl urea under Schotten-Baumann conditions.


proposed reaction pathway

see article for more examples



Key Words

Staudinger Reaction, hydantoins, combinatorial chemistry, carbodiimides, sequential synthesis


ID: J60-Y2008-3670