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

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...

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Bibliographic Details
Published in中国化学：英文版 Vol. 30; no. 10; pp. 2411 - 2422
Main Author 霍景沛 吕梅香 王朝阳 李意忠
Format Journal Article
LanguageEnglish
Published 2012
Subjects
Michael
三唑
合成反应
呋喃酮
有机叠氮化物
目标分子
结构式
酮衍生物
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ISSN1001-604X
1614-7065

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Summary: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.
Bibliography: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.
2（5/4）-furanone, bis-1,2,3-triazole, amino acids, synthetic methods, click chemistry
Huo, Jingpei LO, Meixiang Wang, Zhaoyang Li, Yizhong School of Chemistry and Environment, South China Normal University, Guangzhou, Guangdong 510006, China
31-1547/O6
ISSN:1001-604X
1614-7065