CuI-Catalyzed tandem intramolecular amidation using gem-dibromovinyl systems.
[reaction: see text] Imidazoindolones are present as the key structural motif in the family of antifungals, fumiquinazolines, and the antagonist asperlicin. The first example of a CuI-catalyzed tandem intramolecular amidation forming substituted imidazoindolones from readily accessible ortho gem-dibromovinylanilines is described.
Davenport Chemistry Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
Josephine
J
Yuen
Yuan-Qing
YQ
Fang
Mark
M
Lautens
D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D001570:Benzodiazepinones / Q000138:chemical synthesis; D002384:Catalysis; D002766:Cholecystokinin / Q000037:antagonists & inhibitors; D003300:Copper / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D011799:Quinazolines / Q000737:chemistry / Q000494:pharmacology; D014753:Vinyl Compounds / Q000737:chemistry*
D000935:Antifungal Agents; D001570:Benzodiazepinones; D006842:Hydrocarbons, Brominated; D007093:Imidazoles; D007211:Indoles; D011799:Quinazolines; D014753:Vinyl Compounds; C419468:fumiquinazoline A; D003300:Copper; D002766:Cholecystokinin; C046367:asperlicin