Copper(I)-catalyzed one-pot synthesis of 2H-1,4-benzoxazin-3-(4H)-ones from o-halophenols and 2-chloroacetamides.
We developed an efficient and convenient method for preparing N-substituted 2H-1,4-benzoxazin-3-(4H)-ones from 2-halophenols via a nucleophilic substitution with 2-chloroacetamides followed by a CuI-catalyzed coupling cyclization. A broad spectrum of substrates can be effectively employed to afford the desired products in good yields. Since this method involves simple reaction conditions, a short reaction time, and a broad substrate scope, it is particularly attractive for the efficient preparation of biologically and medicinally interesting molecules.
Feng
Enguang
E
The Center for Drug Discovery and Design, State Key Laboratory of Drug Research, Shanghai Institutes for Biological Sciences, Chinese Academy of Sciences, Shanghai, 201203, China.
Huang
He
H
Zhou
Yu
Y
Ye
Deju
D
Jiang
Hualiang
H
Liu
Hong
H
D000578:Amidines / Q000737:chemistry*; D048588:Benzoxazines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006219:Halogens / Q000737:chemistry*; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*
C509120:2-chloroacetamidine; D000578:Amidines; D048588:Benzoxazines; D006219:Halogens; D010636:Phenols; D003300:Copper