An efficient and straightforward two-step procedure for the synthesis of N-1 alkyl/aryl-substituted hydantoins was developed, starting from easily available starting materials. The procedure envisages a highly regiospecific domino condensation/ aza-Michael (nucleophilic substitution)/O->N acyl migration between activated α,β-unsaturated carboxylic acids or α-haloaryl acetic acids, respectively, and N-tert-butyl- or N-tritylcarbodiimides, leading to the regioselective formation of hydantoins bearing the tertiary alkylic substituent in the 3-position, followed by selective removal the substituent. This process avoids the use of harsh reaction conditions and toxic reagents and is high yielding. A detailed study of the influence of the structure of the reactants on the reaction outcome is presented. A wide variety of final products having a primary, secondary, cyclic and aryl substituent at the N-1 position were successfully synthesized by this method.

A Mild, Efficient Approach for the Synthesis of 1,5-Disubstituted Hydantoins / F. Olimpieri, M.C. Bellucci, A. Volonterio, M. Zanda. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - 2009:35(2009), pp. 6179-6188. [10.1002/ejoc.200900868]

A Mild, Efficient Approach for the Synthesis of 1,5-Disubstituted Hydantoins

M.C. Bellucci
Secondo
;
2009

Abstract

An efficient and straightforward two-step procedure for the synthesis of N-1 alkyl/aryl-substituted hydantoins was developed, starting from easily available starting materials. The procedure envisages a highly regiospecific domino condensation/ aza-Michael (nucleophilic substitution)/O->N acyl migration between activated α,β-unsaturated carboxylic acids or α-haloaryl acetic acids, respectively, and N-tert-butyl- or N-tritylcarbodiimides, leading to the regioselective formation of hydantoins bearing the tertiary alkylic substituent in the 3-position, followed by selective removal the substituent. This process avoids the use of harsh reaction conditions and toxic reagents and is high yielding. A detailed study of the influence of the structure of the reactants on the reaction outcome is presented. A wide variety of final products having a primary, secondary, cyclic and aryl substituent at the N-1 position were successfully synthesized by this method.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/171291
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