First domino radical cyclisation/Smiles rearrangement combinationElectronic supplementary information (ESI) available: Experimental details, 1H NMR and 13C NMR spectra of all products and crystallographic data of 7e1. CCDC 825601 (7e1). For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c2cc15670a

An unprecedented domino radical cyclisationSmiles rearrangement process affording 3-(2-aryl- N -methyl acetamido)indolin-2-ones is presented. Experimental rationalisation of this approach and description of an unexpected tricyclic core are also handled. We have developed for the first time a domino radical cyclisationSmiles rearrangement procedure affording oxindoles ( 5 ) and tricyclic products ( 7 ) depending on reaction conditions.