An efficient route from coumarins to highly functionalized N-phenyl-2-quinolinones via Buchwald-Hartwig amination

Multiple substituted N-phenyl-2-quinolinones were obtained in a convenient four-step route from a variety of commercially available coumarins, utilizing customised Buchwald-Hartwig amination protocols for the key reaction. Whereas simple aminolysis of coumarins is limited to non-electron-deficient, sterically unhindered derivatives of aniline under harsh conditions, the present method allows for conversions with multiple substituted aromatic amines, as demonstrated by the example of chlorinated aminosalicylates. (C) 2003 Elsevier Science Ltd. All rights reserved.