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Synlett 2008(19): 3016-3020  
DOI: 10.1055/s-0028-1087352
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Francesca Olimpieria, Alessandro Volonterio*a,b, Matteo Zanda*b
a Dipartimento di Chimica, Materiali e Ingegneria Chimica ‘Giulio Natta’, Politecnico di Milano, Via Mancinelli 7, 20131 Milano, Italy
Fax: +39(02)23993080; e-Mail: alessandro.volonterio@polimi.it;
b C.N.R., Istituto di Chimica del Riconoscimento Molecolare, Sezione ‘A. Quilico’, Via Mancinelli 7, 20131 Milano, Italy
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Publication History

Received 6 August 2008
Publication Date:
12 November 2008 (online)

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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.

Key words

heterocycles - multicomponent reactions - combinatorial chemistry - carbodiimides - sequential synthesis

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11

The reaction was carried out in dioxane because carbodiimide 2f was insoluble in CH2Cl2.

12

The lower yields obtained with N,N′-dialkylcarbodiimides in the three-component process are probably due to lower yields in the Staudinger reaction.