Pest und Geschrei in Dosen?

Abstract

An efficient method was developed for the functionalization of nitroquinolines by employing pericyclic [3+2] and [4+2] cycloaddition reactions. The facile dearomatization of the nitrated benzene ring under the action of unstabilized N‐alkyl azomethine ylides and dienes led to fused heterocyclic systems. The 1,3‐dipoles smoothly and selectively underwent a cycloaddition reaction with the CC(NO2) fragment of the aromatic system if the position ortho to the nitro group was vacant, whereas the [4+2] cycloaddition of dienes required a furoxan ring to be annulated to the quinoline moiety.