A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes

Department of Chemistry & Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208, USA.
Organic Letters (Impact Factor: 6.32). 12/2004; 6(24):4603-6. DOI: 10.1021/ol047955x
Source: PubMed

ABSTRACT Copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of nonfluorescent 3-azidocoumarins and terminal alkynes afforded intense fluorescent 1,2,3-triazole products. The mild condition of this reaction allowed us to construct a large library of pure fluorescent coumarin dyes. Since both azide and alkyne are quite inert to biological systems, this reaction has potential in bioconjugation and bioimaging applications. [reaction: see text]

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