Synthesis of 2(5H)-Furanone Derivatives with Bis-1,2,3-triazole Structure

• Published in: Chinese journal of chemistry 2012-10, Vol.30 (10), p.2411-2422
• Main Authors: Huo, Jingpei, LÜ, Meixiang, Wang, Zhaoyang, Li, Yizhong
• Format: Article
• Language: English
• Subjects: 2(5H)-furanone; 3-triazole; Amino acids; bis-1; bis‐1,2,3‐triazole; click chemistry; synthetic methods
• ISSN: 1001-604X; 1614-7065
• DOI: 10.1002/cjoc.201200638

A series of new chiral 2(5H)‐furanone derivatives containing bis‐1,2,3‐triazole moiety were designed and synthesized from (5S)‐5‐alkoxy‐3,4‐dihalo‐2(5H)‐furanones 1, dicarboxyl amino acids 2, propargyl bromide, and organic azides 5 under mild conditions via the sequential three steps, including asymmetric Michael addition‐elimination, substitution and no‐ligand click reaction. Twelve new intermediates, including N‐[5‐alkoxy‐2(5H)‐furanonyl] dicarboxyl amino acids 3 and their corresponding propargyl esters 4, and twelve target molecules 6 were characterized by FTIR, 1H NMR, 13C NMR, MS and elemental analysis. The influences of different synthetic conditions and substrates in each step were investigated. The research provides a new method and idea for the synthesis of 2(5H)‐furanone compounds with polyheterocyclic structure due to the diversities of four basic unit molecules. A series of new chiral 2(5H)‐furanone derivatives containing bis‐1,2,3‐triazole moiety are designed and synthesized from 4 basic unit molecules under mild conditions via the sequential three steps, including asymmetric Michael addition‐elimination, substitution and no‐ligand click reaction.