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Issue 15, 2010
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Formation and reactions of azepino[4,5-b]indoles: an unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinones

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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

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Article information


Submitted
04 Mar 2010
Accepted
14 May 2010
First published
08 Jun 2010

Org. Biomol. Chem., 2010,8, 3563-3570
Article type
Paper

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

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