Organic letters

Heterocycle Annulation of Enolizable Vinyl Quinone Imides. Dihydroquinolines and Quinolines from Thermal 6π-Electrocyclizations and Indoles from Photochemical …

KA Parker, TL Mindt

Index: Parker, Kathlyn A.; Mindt, Thomas L. Organic Letters, 2002 , vol. 4, # 24 p. 4265 - 4268

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Citation Number: 35

Abstract

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.