1263214-77-2Relevant academic research and scientific papers
Novel triazolyl derivatives for acidic release of amines
Delatouche, Regis,Mondon, Martine,Gil, Adri,Frapper, Gilles,Bachmann, Christian,Bertrand, Philippe
, p. 401 - 407 (2011)
Triazolyl derivatives of amines were prepared using click chemistry and evaluated as releasing systems in mildly acidic environments. Triazolylcarbamates and alkylamines were obtained, depending on the reactivity of the propargylic intermediates used for the Huisgen cycloaddition. A fast hydrolysis of some derivatives in mildly acidic conditions was achieved. The relative rates were correlated to a proposed mechanism highlighting the complementary role of the triazole ring and carbocation reactivity/stability. Copyright
Extending triazolyl-based release under mildly acidic conditions to give aniline derivatives
Delatouche, Regis,Bachmann, Christian,Frapper, Gilles,Bertrand, Philippe
scheme or table, p. 1090 - 1094 (2012/05/20)
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 me
Triazolyl derivatives for acidic release of alcohols
Mondon, Martine,Delatouche, Regis,Bachmann, Christian,Frapper, Gilles,Len, Christophe,Bertrand, Philippe
supporting information; experimental part, p. 2111 - 2119 (2011/05/16)
New triazolyl-based carbonates and ethers have been investigated as potential alcohol-releasing systems under mild acidic conditions. Triazolyl carbonates could not be prepared because of their apparent instability, whereas ethers were successfully obtained. The rate of hydrolysis of these ethers ramged from a few hours to several days. A theoretical investigation demonstrated that the acidic release of alcohols from triazole derivatives proceeds first by protonation of the triazole ring followed by proton transfer from the triazole ring to the carbonyl group of the carbonates or to the oxygen atom of the ether derivatives. The rate of the decomposition reaction was shown to depend on the length of the N3-H···O hydrogen bond in the intermediate C-NH+/E-NH+ structures and on the stability of the triazole carbocation, which is closely related to the π-donating effect of its R2 and R3 substituents. Copyright
