146919-85-9Relevant academic research and scientific papers
Aqueous copper nitrate catalyzed synthesis of 3-alkylideneoxindoles from α-diazo-ketoanilides
Mo, Shanyan,Yang, Zhanhui,Xu, Jiaxi
, p. 3923 - 3929 (2014/06/24)
An economical, practical, and green protocol with which to synthesize 3-alkylideneoxindoles from α-diazo-ketoanilides has been developed. The approach employs inexpensive Cu(NO3)2·3H 2O as catalyst and environmentally friendly water as solvent, and achieves moderate to excellent yields. The method has good tolerance to a range of N-alkyl and N-aryl groups, including electron-withdrawing and electron-donating groups on the aromatic ring, ortho-, meta-, and para-substituents, and -aliphatic and -aromatic keto groups. A plausible mechanism involving intramolecular aromatic metal carbene electrophilic addition as the key step is proposed. Inexpensive Cu(NO3)2· 3H2O catalyst and environmentally friendly water solvent are employed for the transformation of α-diazo-ketoanilides into 3-alkylidene- oxindoles. The process is easily handled, economical, environmentally friendly, and can be used to convert a broad range of substrates in moderate to excellent yields. An intramolecular aromatic metal carbene electrophilic addition mechanism is proposed. Copyright
2-Hydroxyindole Compounds. Alkylation of 3-Acetyl-1-benzyl-2-hydroxy-5-methoxyindole Under Basic Conditions
Huegel, Helmut M.,Greenwood, Richard J.,Mackay, Maureen F.
, p. 1953 - 1959 (2007/10/02)
Alkylation of 3-acetyl-1-benzyl-2-hydroxy-5-methoxyindole with benzyl bromide in the presence of base resulted in isolation of the C-alkylated product which has been shown by X-ray crystallographic analysis to be 3-acetyl-1,3-dibenzyl-5-methoxy-1,3-dihydr
