A sequential Friedländer and anionic benzannulation strategy for the regiodefined assembly of unsymmetrical acridines

Abstract

An efficient sequential double-annulation strategy has been developed to afford a series of unsymmetrical acridines with high yield and regioselectivity for the first time. This simple protocol enables the sequential assembly of two aromatic rings from simple starting materials. The reaction proceeds via modified Friedländer annulation and subsequent base-mediated benzannulation with acrylates as Michael acceptors. A range of substrate scope and functional group tolerance is observed. Late-stage synthetic modification is also explored to access novel unsymmetrical acridines in good yield.