Regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles from enaminones.
A highly regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles from enaminones based on reaction condition selection is reported. 3-Arylaminoisoxazoles were produced by treating enaminones with aqueous hydroxylamine in DMF at 100 °C, whereas 5-arylaminoisoxazoles were synthesized by subjecting enaminones to aqueous hydroxylamine in the presence of KOH and TBAB in water under reflux. A mechanism for the regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles is proposed.
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China.
Dexuan
D
Xiang
Xiaoqing
X
Xin
Xu
X
Liu
Rui
R
Zhang
Jiming
J
Yang
Dewen
D
Dong
D000586:Amination; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D007555:Isoxazoles