Sc(OTf)3-catalyzed dehydrogenative cyclization for synthesis of N-methylacridones
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 (SEAr) 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.
Li, Xi-An,Wang, Hong-Li,Yang, Shang-Dong
supporting information
p. 1794 - 1797
(2013/05/23)
Regioselective copper-catalyzed amination of bromobenzoic acids using aliphatic and aromatic amines
A chemo- and regioselective copper-catalyzed cross-coupling procedure for amination of 2-bromobenzoic acids is described. The method eliminates the need for acid protection and produces N-aryl and N-alkyl anthranilic acid derivatives in up to 99% yield. N-(1-Pyrene)anthranilic acid has been employed in metal ion-selective fluorosensing. Titration experiments showed that this pyrene-derived amino acid forms an equimolar complex with Hg(II) in water resulting in selective fluorescence quenching even in the presence of other metal ions such as Zn(II) and Cd(II).
Wolf, Christian,Liu, Shuanglong,Mei, Xuefeng,August, Adam T.,Casimir, Michael D.
p. 3270 - 3273
(2007/10/03)
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