Premium
Synthesis of 2(5 H )‐Furanone Derivatives with Bis‐1,2,3‐triazole Structure
Author(s) -
Huo Jingpei,
LÜ Meixiang,
Wang Zhaoyang,
Li Yizhong
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201200638
Subject(s) - chemistry , moiety , propargyl , propargyl bromide , alkoxy group , bromide , triazole , molecule , click chemistry , carbon 13 nmr , stereochemistry , ligand (biochemistry) , combinatorial chemistry , proton nmr , medicinal chemistry , organic chemistry , catalysis , alkyl , biochemistry , receptor
A series of new chiral 2(5 H )‐furanone derivatives containing bis‐1,2,3‐triazole moiety were designed and synthesized from (5 S )‐5‐alkoxy‐3,4‐dihalo‐2(5 H )‐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(5 H )‐furanonyl] dicarboxyl amino acids 3 and their corresponding propargyl esters 4 , and twelve target molecules 6 were characterized by FTIR, 1 H NMR, 13 C 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(5 H )‐furanone compounds with polyheterocyclic structure due to the diversities of four basic unit molecules.