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

作　　者：霍景沛 吕梅香 汪朝阳 李意忠 

机构地区：[1]School of Chemistry and Environment,South China Normal University,Guangzhou,Guangdong 510006,China

出　　处：《Chinese Journal of Chemistry》2012年第10期2411-2422,共12页中国化学（英文版）

基　　金：We are grateful to the National Natural Science Foundation of China （No. 20772035）, the Third Talents Special Funds of Guangdong Higher Education （No. Guangdong-Finance-Education [2011]431） and the Natural Science Foundation of Guangdong Province （No. S2011010001556） for financial support.

摘　　要：A series of new chiral 2（5H）-furanone derivatives containing bis-l,2,3-triazole moiety were designed and syn- thesized from （5S）-5-alkoxy-3,4-dihalo-2（5H）-furanones 1, dicarboxyl amino acids 2, propargyl bromide, and or- ganic azides 5 under mild conditions via the sequential three steps, including asymmetric Michael addi- tion-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 syn- thetic 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-l,2,3-triazole moiety were designed and syn- thesized from （5S）-5-alkoxy-3,4-dihalo-2（5H）-furanones 1, dicarboxyl amino acids 2, propargyl bromide, and or- ganic azides 5 under mild conditions via the sequential three steps, including asymmetric Michael addi- tion-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 syn- thetic 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.

关 键 词：2（5/4）-furanone bis-1 2 3-triazole amino acids synthetic methods click chemistry 

分 类 号：O626.11[理学—有机化学] TQ223.121[理学—化学]