One-Pot, Regioselective Synthesis of 1,3,5 Trisubstituted Hydantoins by Domino Condensation / aza-Michael / O→N acyl Migration of Asymmetric Carbodiimides with α,β-Unsaturated Carboxylic Acids

Alessandro      Volonterio; Matteo      Zanda

doi:10.2174/1570178053400298

Abstract

1,3,5 Trisubstituted hydantoins having two different substituents at the nitrogen atoms could be smoothly prepared by a domino condensation / aza-Michael / O→N acyl migration of asymmetric carbodiimides with activated α,β-unsaturated carboxylic acids. The regiochemical outcome of the process, as well as scope and limits, are discussed.

Keywords: hydantoins, domino reaction, aza-michael, carbodiimides, regiochemistry

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Letters in Organic Chemistry

Title: One-Pot, Regioselective Synthesis of 1,3,5 Trisubstituted Hydantoins by Domino Condensation / aza-Michael / O→N acyl Migration of Asymmetric Carbodiimides with α,β-Unsaturated Carboxylic Acids

Volume: 2 Issue: 1

Author(s): Alessandro Volonterio and Matteo Zanda

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Keywords: hydantoins, domino reaction, aza-michael, carbodiimides, regiochemistry

Abstract: 1,3,5 Trisubstituted hydantoins having two different substituents at the nitrogen atoms could be smoothly prepared by a domino condensation / aza-Michael / O→N acyl migration of asymmetric carbodiimides with activated α,β-unsaturated carboxylic acids. The regiochemical outcome of the process, as well as scope and limits, are discussed.

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Volonterio Alessandro and Zanda Matteo, One-Pot, Regioselective Synthesis of 1,3,5 Trisubstituted Hydantoins by Domino Condensation / aza-Michael / O→N acyl Migration of Asymmetric Carbodiimides with α,β-Unsaturated Carboxylic Acids, Letters in Organic Chemistry 2005; 2 (1) . https://dx.doi.org/10.2174/1570178053400298