Electrophile-induced dearomatizing spirocyclization of N-arylisonicotinamides: a route to spirocyclic piperidines.
Treatment of N-arylisonicotinamides with trifluoromethanesulfonic anhydride triggers intramolecular nucleophilic attack of the aryl ring on the 4-position of the pyridinium intermediate. The products are spirocyclic dihydropyridines which can be converted to valuable spirocyclic piperidines related to biologically active molecules such as MK-677.
Arnott
Gareth
G
School of Chemistry, University of Manchester, Manchester, UK.
Brice
Heloise
H
Clayden
Jonathan
J
Blaney
Emma
E
D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D009536:Niacinamide / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D010880:Piperidines; D013141:Spiro Compounds; D009536:Niacinamide; C027681:isonicotinamide