The author of 《A tandem coupling/Smiles rearrangement/cyclization approach to 1,4-benzoxazinone or 1,4-pyridooxazinones under mild conditions》 were Zhan, Chunjing; Jia, Jiong; Yang, Bingchuan; Huang, Aiping; Liu, Yanli; Ma, Chen. And the article was published in RSC Advances in 2012. Related Products of 4746-61-6 The author mentioned the following in the article:
A facile and efficient approach to 1,4-benzoxazinone or 1,4-pyridooxazinone scaffolds is developed by a Smiles rearrangement tandem reaction. 1,4-Benzoxazinone derivatives or 1,4-pyridooxazinone derivatives with diversity at two substituents on their scaffolds were synthesized conveniently in the presence of cesium carbonate at room temperature in good to excellent yields. The reaction mechanism is assumed by a tandem coupling/Smiles rearrangement/cyclization process. The synthesis of the target compounds was achieved using fluoro(nitro)benzene derivatives and chloro(nitro)benzene derivatives and 2-hydroxyacetamide derivatives as starting materials. The title compounds thus formed included 3,4-dihydro-3-oxo-4-phenyl-2H-1,4-benzoxazine-7-carbonitrile (I), 4-(phenylmethyl)-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (II), 5-chloro-4-(phenylmethyl)-2H-1,4-benzoxazin-3(4H)-one (III) and related substances. The experimental process involved the reaction of 2-Hydroxy-N-phenylacetamide(cas: 4746-61-6Related Products of 4746-61-6)
2-Hydroxy-N-phenylacetamide(cas: 4746-61-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole.Related Products of 4746-61-6 The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics