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

Ajay Verma; Saket Patel; Meenakshi; Amit Kumar; Abhimanyu Yadav; Shailesh Kumar; Sadhan Jana; Shubham Sharma; Ch Durga Prasad; Sangit Kumar

doi:10.1039/c4cc08717h

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

Chem Commun (Camb). 2015 Jan 25;51(7):1371-4. doi: 10.1039/c4cc08717h.

Authors

Ajay Verma¹, Saket Patel, Meenakshi, Amit Kumar, Abhimanyu Yadav, Shailesh Kumar, Sadhan Jana, Shubham Sharma, Ch Durga Prasad, Sangit Kumar

Affiliation

¹ Department of Chemistry, Indian Institute of Science Education and Research (IISER) Bhopal, Indore By-pass Road, Bhauri, Bhopal, Madhya Pradesh, India-462 066. sangitkumar@iiserb.ac.in.

PMID: 25487732
DOI: 10.1039/c4cc08717h

Abstract

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.