Thermal rearrangement of indolyl oxime esters to pyridoindoles.
Acyl oximes derived from a variety of indolylalkanones underwent a ring closure sequence during FVP to afford 9H-pyrido[2,3-b]indoles. Unlike UV light promoted reactions of oxime esters, the mechanism is almost certainly not mediated by iminyl radicals but probably involves tautomerism, elimination of acetic acid, and a final electrocyclic ring closure.
Portela-Cubillo
Fernando
F
School of Chemistry, EaStChem, University of St. Andrews, St. Andrews, Fife KY16 9ST, UK.
Surgenor
Brian A
BA
Aitken
R Alan
RA
Walton
John C
JC