Transition metal free intramolecular selective oxidative C(sp3)-N coupling: synthesis of N-aryl-isoindolinones from 2-alkylbenzamides

A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp(3))-H and N-H bonds utilizing iodine, potassium ca...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2015-01, Vol.51 (7), p.1371-1374
Main Authors: Verma, Ajay, Patel, Saket, Meenakshi, Kumar, Amit, Yadav, Abhimanyu, Kumar, Shailesh, Jana, Sadhan, Sharma, Shubham, Prasad, Ch Durga, Kumar, Sangit
Format: Article
Language:English
Subjects:
Acetonitrile
Chemical bonds
Coupling
Drugs
Iodine
Peroxides
Synthesis
Transition metals
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Summary:A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp(3))-H and N-H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110-140 °C.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc08717h