Organic Letters 2008-07-17

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

Gareth Arnott, Heloise Brice, Jonathan Clayden, Emma Blaney

Index: Org. Lett. 10(14) , 3089-92, (2008)

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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.