title: PhI(OCOCF3)2-Mediated Cyclization of o-(1-Alkynyl)benzamides: Metal-Free Synthesis of 3-Hydroxy-2,3-dihydroisoquinoline-1,4-dione.
abstract: The synthesis of an undocumented skeleton of 3-hydroxy-2,3-dihydroisoquinoline-1,4-diones has been discovered and reported. The reaction consists of an intramolecular cyclization of o-(1-alkynyl)benzamides in MeCN/H2O, mediated by metal-free, hypervalent reagent of PhI(OCOCF3)2, followed by an oxidative hydroxylation reaction. The mechanism consisting of two pathways has been proposed and discussed.
authors.forename: Chao
authors.initials: C
authors.lastname: Yang
authors.forename: Xiang
authors.initials: X
authors.lastname: Zhang
authors.forename: Daisy
authors.initials: D
authors.lastname: Zhang-Negrerie
authors.affiliation: ‡Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300072, China.
authors.forename: Yunfei
authors.initials: Y
authors.lastname: Du
authors.forename: Kang
authors.initials: K
authors.lastname: Zhao
mesh_terms: D001549:Benzamides / Q000737:chemistry*; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D003500:Cyclization; D006900:Hydroxylation; D007202:Indicators and Reagents / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C000603894:3-hydroxy-2,3-dihydroisoquinoline-1,4-dione; D001549:Benzamides; D056831:Coordination Complexes; D007202:Indicators and Reagents; D007546:Isoquinolines; D008670:Metals; D012238:Rhodium