title: Sc(OTf)3-catalyzed dehydrogenative cyclization for synthesis of N-methylacridones.
abstract: A novel method has been developed for the synthesis of substituted N-methylacridones from 2-(N-methyl-N-phenylamino)benzaldehydes via dehydrogenative cyclization. This transformation involves two primary processes: the aldehyde first coordinates with Sc(OTf)3 and induces the aromatic electrophilic substitution (S(E)Ar) reaction to form the active intermediate N-methyl-acridin-9-ol, which is then quickly oxidized in situ to afford the acridones. Furthermore, the procedure involved is both environmental friendly and atom efficient; H2O is the only byproduct in this reaction.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, PR China.
authors.forename: Xi-An
authors.initials: XA
authors.lastname: Li
authors.forename: Hong-Li
authors.initials: HL
authors.lastname: Wang
authors.forename: Shang-Dong
authors.initials: SD
authors.lastname: Yang
mesh_terms: D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D012538:Scandium / Q000737:chemistry*
chemical_list: D000166:Acridines; D001547:Benzaldehydes; D008698:Mesylates; C518162:N-methylacridone; C436603:scandium triflate; D012538:Scandium