Jump to main content
Jump to site search

Issue 15, 2010
Previous Article Next Article

Formation and reactions of azepino[4,5-b]indoles: an unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinones

Author affiliations

Abstract

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.

Graphical abstract: Formation and reactions of azepino[4,5-b]indoles: an unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinones

Back to tab navigation

Supplementary files

Publication details

The article was received on 04 Mar 2010, accepted on 14 May 2010 and first published on 08 Jun 2010


Article type: Paper
DOI: 10.1039/C003742G
Citation: Org. Biomol. Chem., 2010,8, 3563-3570
  •   Request permissions

    Formation and reactions of azepino[4,5-b]indoles: an unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinones

    S. G. Stewart, E. L. Ghisalberti, B. W. Skelton and C. H. Heath, Org. Biomol. Chem., 2010, 8, 3563
    DOI: 10.1039/C003742G

Search articles by author

Spotlight

Advertisements