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Synthesis of ( E )‐3‐Alkylideneindolin‐2‐ones by an Iron‐Catalyzed Aerobic Oxidative Condensation of Csp 3 –H Bonds of Oxindoles and Benzylamines
Author(s) -
Gopalaiah Kovuru,
Tiwari Ankit
Publication year - 2020
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.202001300
Subject(s) - chemistry , nucleophile , oxidative phosphorylation , catalysis , amine gas treating , condensation , condensation reaction , combinatorial chemistry , nucleophilic addition , organic chemistry , stereochemistry , medicinal chemistry , biochemistry , physics , thermodynamics
A novel synthetic route for the construction of ( E )‐3‐alkylideneindolin‐2‐ones through iron‐catalyzed aerobic oxidative condensation of oxindoles with benzylamines has been developed. This oxidative reaction involves a sequence of C–H activation, amine self‐condensation, nucleophilic addition, and C–C double bond formation. The synthetic importance of this protocol has been demonstrated by preparing tyrosine kinase inhibitors, anticonvulsant and antitumor agents, and other valuable 3‐alkylideneindolin‐2‐one derivatives. Key intermediates are isolated and a plausible mechanistic pathway for the reaction has been discussed.