title: One-pot synthesis of 3-hydroxyquinolin-2(1H)-ones from N-phenylacetoacetamide via PhI(OCOCF3)2-mediated α-hydroxylation and H2SO4-promoted intramolecular cyclization.
abstract: A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)2-mediated α-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated α-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.
authors: Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
authors: Yucheng
authors: Y
authors: Yuan
authors: Rui
authors: R
authors: Yang
authors: Daisy
authors: D
authors: Zhang-Negrerie
authors: Junwei
authors: J
authors: Wang
authors: Yunfei
authors: Y
authors: Du
authors: Kang
authors: K
authors: Zhao
mesh_terms: D000083:Acetanilides / Q000737:chemistry*; D003500:Cyclization; D006900:Hydroxylation; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013464:Sulfuric Acids / Q000737:chemistry*; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: C584183:3-hydroxyquinolin-2(1H)-one; D000083:Acetanilides; D007462:Iodobenzenes; C584184:N-phenylacetoacetamide; D015363:Quinolones; D013464:Sulfuric Acids; C517666:phenyliodine(III) bis(trifluoroacetate); D014269:Trifluoroacetic Acid; C033158:sulfuric acid