Heterocycle annulation of enolizable vinyl quinone imides. Dihydroquinolines and quinolines from thermal 6pi-electrocyclizations and indoles from photochemical cyclizations.
[reaction: see text] Enolizable vinyl quinone mono- and diimide substrates yield protected 6-hydroxy and 6-amino dihydroquinolines by thermal electrocyclization. Aromatization provides the corresponding quinolines in quantitative yields. The quinone monoimide substrates undergo clean photochemical conversion to 5-hydroxy indoles.
Parker
Kathlyn A
KA
Department of Chemistry, SUNY Stony Brook, Stony Brook, New York 11794-3400, USA. kparker@notes.cc.sunysb.edu
Mindt
Thomas L
TL
D003500:Cyclization; D004563:Electrochemistry; D007094:Imides / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D010777:Photochemistry; D011804:Quinolines / Q000737:chemistry*
D007094:Imides; D007211:Indoles; D011804:Quinolines