Synthesis of potentially photoactivatable coumarin derivatives via a 1,3-dipolar cycloaddition

✍ Scribed by Elodie-Denise Chenot; Juan Carlos Rodríguez-Domínguez; Alain Comel; Gilbert Kirsch; Paul Hannewald

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2008
• Tongue: English
• Weight: 477 KB
• Volume: 45
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570450528

✦ Synopsis

Abstract

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A copper (1)‐catalyzed 1,3‐dipolar cycloaddition reaction was used to prepare a series of mono and disubstituted 1,2,3‐triazolyl‐coumarins using a 1,3‐cycloaddition (“Click Chemistry”). Starting coumarins were synthesized using classical or modified Pechmann's reaction. The propargyl group was introduced as either propargylether or as a propargylamide. Azides were prepared in a three steps procedure. Cycloaddition products, containing a coumarin and a photoactivatable moiety, were obtained in good yields.