Concise synthesis of chiral 2(5H)-furanone derivatives possessing 1,2,3-triazole moiety via one-pot approach

Add time:07/15/2019    Source:sciencedirect.com

Combining three bioactive units, such as 2(5H)-furanone, 1,2,3-triazole, and amino acid together into one potential drug molecule with polyfunctional groups, a series of new chiral 2(5H)-furanone derivatives containing 1,2,3-triazole moiety have been designed and synthesized from (5S)-5-alkoxy-3,4-dibromo-2(5H)-furanones, amino acids, propargyl bromide, and organic azides via the sequential three steps, including asymmetric Michael addition–elimination, substitution, and click reaction. The latter two steps, substitution and click reaction could proceed smoothly in a one-pot process. Furthermore, the target products could be directly synthesized via a four-component one-pot approach.

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