Formation and reactions of azepino[4,5-b]indoles: an unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinonesElectronic supplementary information (ESI) available: Details of molecular structures, hydrogen bonds and NMR spectra. CCDC reference numbers 767164 and 767165. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c003742g

• Main Authors: Stewart, Scott G, Ghisalberti, Emilio L, Skelton, Brian W, Heath, Charles H
• Format: Journal Article
• Language: English
• Published: 14.07.2010
• DOI: 10.1039/c003742g
• ISSN: 1477-0520

Herein we report the formation and interesting reactivity of several azepino[4,5- b ]indole heterocycles. Initially, a key intramolecular Heck reaction is used to efficiently create the azepino[4,5- b ]indole seven membered ring containing an exocyclic double bond. Treatment of the olefin with ozone results in an unprecedented secondary reaction of the Criegee intermediate, through intramolecular olefin trapping, to afford a benzo[ c ]naphthyridione containing a bridging cyclic peroxide. Herein we report the formation and interesting reactivity of several azepino[4,5- b ]indole heterocycles bearing an additional olefin. Treatment of these ring systems with ozone results in an unprecedented secondary reaction of the Criegee intermediate, to afford a benzo[ c ]naphthyridione containing a bridging cyclic peroxide.