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Synthesis 2012(7): 1090-1094  
DOI: 10.1055/s-0031-1289719
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Extending Triazolyl-Based Release under Mildly Acidic Conditions To Give Aniline Derivatives

Régis Delatouche, Christian Bachmann, Gilles Frapper, Philippe Bertrand*
Institut de Chimie des Milieux et Matériaux de Poitiers (IC2MP), UMR 7285 CNRS-Université de Poitiers, 4 rue Michel Brunet, Bâtiment B27, 86022 Poitiers cedex, France
Fax: +33(5)49453501; e-Mail: philippe.bertrand@univ-poitiers.fr;
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Publication History

Received 8 December 2011
Publication Date:
24 February 2012 (online)

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Abstract

Triazolyl derivatives of anilines were prepared and evaluated as releasing systems at mildly acidic pH values. Two triazolyl derivatives showed convenient pH sensitivity, being stable at pH 7.3 and rapidly hydrolyzed at pH values below 5. A generalized mechanism is proposed from additional theoretical investigations.

Key words

hydrolysis - alkynes - azides - cycloaddition - amines - protonation

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