A domino amidation route to indolines and indoles: rapid syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.
[reaction: see text] When subjected to palladium-catalyzed amidation conditions, 2-triflyloxy phenethyl carbonates undergo, in addition to the expected aryl cross-coupling, an additional amidation with net displacement of the carbonate. The result is a one-step synthesis of indolines which may be oxidized to indoles. The utility of the procedure is illustrated by the two- or three-step syntheses of anhydrolycorinone, hippadine, oxoassoanine, and pratosine.
Ganton
Michael D
MD
Department of Chemistry, University of Western Ontario, London, Ontario, Canada N6A 5B7.
Kerr
Michael A
MA
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D000577:Amides; D026121:Indole Alkaloids; D007211:Indoles; D010617:Phenanthridines; C420562:anhydrolycorinone; C512235:oxoassoanine; C102970:pratosine; C039688:hippadine; C057812:indoline