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One‐pot Synthesis of Oxindoles through C−H Alkylation and Intramolecular Cyclization of Azobenzenes with Internal Olefins
Author(s) -
Han Sang Hoon,
Mishra Neeraj Kumar,
Jo Hyeim,
Oh Yongguk,
Jeon Mijin,
Kim Saegun,
Kim Woo Jung,
Lee Jong Suk,
Kim Hyung Sik,
Kim In Su
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201700147
Subject(s) - chemistry , alkylation , intramolecular force , acetic acid , rhodium , catalysis , cationic polymerization , oxindole , organic chemistry , medicinal chemistry , combinatorial chemistry
The rhodium(III)‐catalyzed site‐selective C−H alkylation of azobenzenes and internal olefins, such as maleimides, maleates and fumarates, followed by reductive intramolecular cyclization is described. A cationic rhodium catalyst in the presence of acetic acid additive in dichloroethane solvent was found to be the optimal catalytic system for the construction of ortho ‐alkylated azobenzenes, which smoothly underwent the intramolecular cyclization leading to the formation of C3‐functionalized oxindoles in the presence of zinc powder and acetic acid. The formed oxindole scaffold could be an important asset towards the development of novel bioactive compounds.