6085-21-8Relevant articles and documents
Fluorogenic Strain-Promoted Alkyne-Diazo Cycloadditions
Friscourt, Frédéric,Fahrni, Christoph J.,Boons, Geert-Jan
supporting information, p. 13996 - 14001 (2015/09/28)
Fluorogenic reactions, in which non- or weakly fluorescent reagents produce highly fluorescent products, are attractive for detecting a broad range of compounds in the fields of bioconjugation and material sciences. Herein, we report that a dibenzocyclooctyne derivative modified with a cyclopropenone moiety (Fl-DIBO) can undergo fast strain-promoted cycloaddition reactions under catalyst-free conditions with azides, nitrones, nitrile oxides, as well as mono- and disubstituted diazo-derivatives. Although the reaction with nitrile oxides, nitrones, and disubstituted diazo compounds gave cycloadducts with low quantum yield, monosubstituted diazo reagents produced 1H-pyrazole derivatives that exhibited an approximately 160-fold fluorescence enhancement over Fl-DIBO combined with a greater than 10 000-fold increase in brightness. Concluding from quantum chemical calculations, fluorescence quenching of 3H-pyrazoles, which are formed by reaction with disubstituted diazo-derivatives, is likely due to the presence of energetically low-lying (n,π?) states. The fluorogenic probe Fl-DIBO was successfully employed for the labeling of diazo-tagged proteins without detectable background signal. Diazo-derivatives are emerging as attractive reporters for the labeling of biomolecules, and the studies presented herein demonstrate that Fl-DIBO can be employed for visualizing such biomolecules without the need for probe washout.
PPh3-mediated reactions of diazoimides in water: a facile synthesis of fused triazine derivatives
Muthusamy, Sengodagounder,Srinivasan, Pandurangan
experimental part, p. 1331 - 1334 (2009/07/17)
Triphenylphosphine-mediated reactions of diazoimides in water were carried out under mild conditions to afford several triazine derivatives in high yields. We have demonstrated an environment friendly methodology to synthesize triazine derivatives.
