Fragment-Based Design and Synthesis of Symmetrical bis-Peptidotriazoles Using Alkylidene bis-Amide Formations and
Sini K S1, Arun S2, Shinu V S1
1Research and Post Graduate Department of Chemistry, St. Joseph's College (Autonomous), Devagiri (Affiliated to University of Calicut), Calicut 673008, Kerala State,India.
Abstract:
A novel and efficient fragment-based assembly of symmetrical bis-peptidotraizoles has been developed based on double Sharpless azide-alkyne click chemistry. A new Cu(II) catalyzed protocol with a wide substrate scope was developed for accessing the symmetrical alkylidene bis-azidoamide fragment that yields the products in very good yields at room temperature without employing column purifications. The propargylated β-acetamido ketone fragment was accessed using another Cu(II) catalyzed room temperature MCR protocol. A fast double-click reaction (2 h) of symmetrical alkylidene bis-azidoamides with propargylated β-acetamido ketone fragments leads to the formation of unusual symmetrical bis-peptidotriazoles.
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