Ultrasonic-assisted synthesis of chrysin derivatives linked with 1,2,3-triazoles by 1,3-dipolar cycloaddition reaction.
The 1,3-dipolar cycloaddition reaction between 7-(3-azidopropoxy)-5-hydroxyflavone and phenylacetylene was carried out to investigate the synthesis of 7-(3-(4-phenyl-1,2,3-triazol-1-yl)propoxy)- 5-hydroxyflavone in presence of ultrasound (sono-synthesis) and absence of ultrasound (conventional method) under relatively optimized solvent and catalyst conditions. The reaction rate was notably accelerated with the help of ultrasound irradiation. An experiment was especially carried out for investigating the acceleration mechanism of ultrasound on the cycloaddition. A novel series of chrysin derivatives linked with 1,2,3-triazoles were obtained by the copper(I)-catalyzed 1,3-dipolar Huisgen cycloaddition reaction using t-BuOH/H(2)O (1:1 v/v) as reaction solvents and CuSO(4)·5H(2)O/sodium ascorbate as the catalyst at room temperature in the presence of ultrasound irradiation. Their structures are elucidated by NMR, ESI MS, IR and Elemental analysis.
Jiang
Yuqin
Y
Department of Chemistry, Zhengzhou University, Key Laboratory of Organic Chemistry and Chemical Biology, Henan Province, Zhengzhou, PR China.
Chen
Xiaolan
X
Qu
Lingbo
L
Wang
Junliang
J
Yuan
Jinwei
J
Chen
Senshen
S
Li
Xu
X
Qu
Chen
C
D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005419:Flavonoids / Q000138:chemical synthesis* / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013696:Temperature; D014230:Triazoles / Q000737:chemistry*; D014465:Ultrasonics
D005419:Flavonoids; D012997:Solvents; D014230:Triazoles; C043561:chrysin; D003300:Copper