1341156-06-6Relevant articles and documents
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
