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Université de Fribourg

Application of photoclick chemistry for the synthesis of pyrazoles via 1,3‐dipolar cycloaddition between alkynes and nitrilimines generated in situ

Remy, Richard ; Bochet, Christian G.

In: European Journal of Organic Chemistry, 2018, vol. 2018, no. 3, p. 316–328

The photochemical extrusion of gaseous nitrogen from 2,5-disubstituted tetrazoles to generate reactive nitrilimines in situ represents an efficient and attractive way to form dipoles that can be used to provide useful chemicals via 1,3-dipolar cycloadditions. The concept of “photoclick chemistry” already inspired numerous researchers, who exploited photochemical processes involving...

Université de Fribourg

Preparation of imidazolidin-4-ones and their evaluation as hydrolytically cleavable precursors for the slow release of bioactive volatile carbonyl derivatives

Trachsel, Alain ; Buchs, Barbara ; Godin, Guillaume ; Crochet, Aurélien ; Fromm, Katharina M. ; Herrmann, Andreas

In: European Journal of Organic Chemistry, 2012, no. 14, p. 2837–2854

Imidazolidin-4-ones are suitable in practical applications as hydrolytically cleavable precursors for the controlled release of fragrant aldehydes and ketones. The corresponding profragrances were prepared by treating aliphatic carbonyl compounds with commercially available amino acid amines in the presence of a base to yield mixtures of diastereomers. The two diastereomers isolated from the...