Electrophile-induced dearomatizing spirocyclization of N-arylisonicotinamides: a route to spirocyclic piperidines

Abstract

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.