Anionic N-fries rearrangement of N-carbamoyl diarylamines to anthranilamides. Methodology and application to acridone and pyranoacridone alkaloids.
[reaction: see text] A general alkyllithium/LDA-mediated rearrangement of N-carbamoyl diarylamines 7a-g into the anthranilamides 8a-g and 9a-g (Table 1) is presented and applied to a regioselective efficient construction of acridone (17) and pyranoacridone (18) alkaloids (Scheme 4).
MacNeil
Stephen L
SL
Department of Chemistry, Queen's University, Kingston, Ontario K7L 3N6, Canada.
Wilson
Brian J
BJ
Snieckus
Victor
V
D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D054831:Acridones; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D062367:ortho-Aminobenzoates / Q000737:chemistry*
D000166:Acridines; D054831:Acridones; D000470:Alkaloids; D000588:Amines; D062367:ortho-Aminobenzoates; C041300:acridone; C000219:anthranilamide