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Aqueous Copper Nitrate Catalyzed Synthesis of 3‐Alkylideneoxindoles from α‐Diazo‐β‐ketoanilides
Author(s) -
Mo Shanyan,
Yang Zhanhui,
Xu Jiaxi
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402206
Subject(s) - chemistry , diazo , electrophile , intramolecular force , carbene , catalysis , electrophilic aromatic substitution , aryl , aqueous solution , cyclopropanation , environmentally friendly , medicinal chemistry , organic chemistry , functional group , alkyl , combinatorial chemistry , ecology , polymer , biology
An economical, practical, and green protocol with which to synthesize 3‐alkylideneoxindoles from α‐diazo‐β‐ketoanilides has been developed. The approach employs inexpensive Cu(NO 3 ) 2 · 3H 2 O 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 β‐aliphatic and β‐aromatic keto groups. A plausible mechanism involving intramolecular aromatic metal carbene electrophilic addition as the key step is proposed.