Formation and reactions of azepino[4,5-b]indoles: an unprecedented ozone reaction in the formation of novel benzo[c]naphthyridinones.
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.
The School of Biomedical, Biomolecular & Chemical Sciences, The University of Western Australia, Crawley, WA 6009, Australia. sgs@cyllene.uwa.edu.au
Scott G
SG
Stewart
Emilio L
EL
Ghisalberti
Brian W
BW
Skelton
Charles H
CH
Heath
D000475:Alkenes / Q000737:chemistry; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009287:Naphthyridines / Q000737:chemistry*; D010126:Ozone / Q000737:chemistry*
D000475:Alkenes; D001381:Azepines; D007211:Indoles; D009287:Naphthyridines; C540210:azepino(4,5-b)indolone; D010126:Ozone