Preparation of peri-annulated indoles from polynitro compounds

A novel peri-annulated heterocyclic system of 1,2-dihydrobenz[6,7]oxepino[4,3,2-cd]indole was prepared starting from TNT via 4,6-dinitro-1-tosylindoline as a key intermediate. Base-induced C=C bond shift in 1,2-dihydrobenz[6,7]oxepino[4,3,2-cd]indoles affords isomeric 2,11-dihydrobenz[6,7]oxepino[4,3,2-cd]indoles. (C) 2009 Elsevier Ltd. All rights reserved.