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Copper(I)-catalyzed one-pot synthesis of 2H-1,4-benzoxazin-3-(4H)-ones from o-halophenols and 2-chloroacetamides. 2009

Enguang Feng, and He Huang, and Yu Zhou, and Deju Ye, and Hualiang Jiang, and Hong Liu
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.

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.

UI MeSH Term Description Entries
D010636 Phenols Benzene derivatives that include one or more hydroxyl groups attached to the ring structure.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D003300 Copper A heavy metal trace element with the atomic symbol Cu, atomic number 29, and atomic weight 63.55. Copper-63,Copper 63
D006219 Halogens A family of nonmetallic, generally electronegative, elements that form group 17 (formerly group VIIa) of the periodic table. Halogen,Group 17 Elements,Elements, Group 17
D000578 Amidines Derivatives of oxoacids RnE(
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D048588 Benzoxazines OXAZINES with a fused BENZENE ring. Benzoxazine,Benzoxazinoid,Benzoxazinone,Benzoxazinones,Benzoxazinoids

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