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

Gareth Arnott, Heloise Brice, Jonathan Clayden*, Emma Blaney

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

40 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)3089-3092
Number of pages4
JournalOrganic Letters
Volume10
Issue number14
Early online date14 Jun 2008
DOIs
Publication statusPublished - 17 Jul 2008

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