SEARCH

SEARCH BY CITATION

Keywords:

  • azides;
  • cyclization;
  • radical reactions;
  • reactive intermediates;
  • spiro compounds
Thumbnail image of graphical abstract

Ipsoeasy: Cyclization of aryl radicals at the ipso-position of p-azido-substituted benzamides or 2-phenylacetamides results in effective production of spirocyclohexadieniminyl radicals through prompt elimination of molecular nitrogen by transient azidocyclohexadienyl radicals. The resultant iminyl radicals can be exploited for the synthesis of oxindoles or quinolones bearing spiro-cyclohexadienimine/cyclohexadienone rings (see picture, TTMSS=tris(trimethylsilyl)silane).