Nitrogen heterocycles are one of the prominent structural components which are frequently approved as small-molecule drugs by U.S. FDA. exhibiting various biological activities. In this work, novel approaches for the synthesis of indoloquinoline and carbocycle-fused quinolone have been developed employing alkynylarylketone derivatives as key precursors. The reaction underwent a domino N2-extrusion/aryl migration to generate carbodiimidium ion and nitrilium ion intermediates in situ for the synthesis of indoloquinolines and carbocycle-fused quinolines, respectively. Then, these intermediates further cyclized to give the corresponding products in moderate to good yields.

Novel domino N2-extrusion/cyclization approaches for the synthesis of indoloquinolines and carbocycle-fused quinolines

2019 Fall National Meeting

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