Synthesis of 1-Azabenzanthracene: Epimerization with the Use of 1,3-Dihydrobenzo(c)thiophene -S,S Dioxide as a Source of ortho-Quinodimethane

Abstract

The cycloaddition of o-quinodimethane, from 1,3-dihydrobenzo(c)-S,S dioxide, to 5,6-dihydroquinoline yields a mixture of adducts isomeric at the newly created ring junction. The cycloadducts can be dehydrogenated to the fully aromatic 1-azabenzanthracene.