Stereoselective synthesis of bio-hybrid amphiphiles of coumarin derivatives by Ugi–Mannich triazole randomization using copper catalyzed alkyne azide click chemistry

An efficient synthesis of ester-triazole-amide amphiphiles of coumarin derivatives by triazole randomization based on click approach is described. Twenty-five small peptide azides were synthesized using Ugi or alternate Mannich-type multi-component reactions. The new azides were then used for the triazole randomization of alkyne functionalized coumarin ester under CuAAC conditions. Sixty-five new peptide bio-hybrids are obtained in near quantitative yield with high regio and stereoselectivity.

Graphical abstractSixty five examples.Figure optionsDownload full-size imageDownload as PowerPoint slide