Uncatalysed Domino Reaction in Hexafluoroisopropanol: A Simple Protocol for the Synthesis of Tetrahydroquinoline Derivatives

Andrea Di Salvo; Maria Vittoria Spanedda; Michèle Ourévitch; Benoit Crousse; Danièle Bonnet-Delpon

doi:10.1055/s-2003-41074

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Uncatalysed Domino Reaction in Hexafluoroisopropanol: A Simple Protocol for the Synthesis of Tetrahydroquinoline Derivatives

Andrea Di Salvo, Maria Vittoria Spanedda, Michèle Ourévitch, Benoit Crousse, Danièle Bonnet-Delpon*
BioCIS, Centre d’Etudes Pharmaceutiques, rue J. B. Clément, 92296 Châtenay-Malabry Cedex, France
Fax: +33(1)46835740; e-Mail: daniele.bonnet-delpon@cep.u-psud.fr;

Abstract

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Abstract

A range of tetrahydroquinolines were synthesised in excellent yields through a domino reaction performed in hexafluoropropanol, starting from anilines and enol ethers and in the absence of Lewis acid catalysis. This solvent was shown to promote the nucleophilic addition of anilines to enol ethers as well as the aza-Diels-Alder reaction.

Key words

Diels-Alder reactions - domino reactions - cycloaddition - nucleophilic additions - 1,1,1,3,3,3-hexafluoro-2-propanol

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References

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