An amine template strategy to construct successive C–C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade†
Timothy Patrick McFadden,Chideraa Iheanyi Nwachukwu,Andrew George Roberts
Organic & Biomolecular Chemistry Pub Date : 01/27/2022 00:00:00 , DOI:10.1039/D1OB02245H
Abstract

We developed a convergent strategy to build, cyclize and excise nitrogen from tertiary amines for the synthesis of polyheterocyclic aromatics. Biaryl-linked azepine intermediates can undergo a deaminative ring contraction cascade reaction, excising nitrogen with the formation of an aromatic core. This strategy and deaminative ring contraction reaction are useful for the synthesis of benzo[h]quinolines.

Graphical abstract: An amine template strategy to construct successive C–C bonds: synthesis of benzo[h]quinolines by a deaminative ring contraction cascade