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

Gareth Arnott; Heloise Brice; Jonathan Clayden; Emma Blaney

doi:10.1021/ol801092s

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

School of Chemistry

Research output: Contribution to journal › Article (Academic Journal) › peer-review

42 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 language	English
Pages (from-to)	3089-3092
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	14
Early online date	14 Jun 2008
DOIs	https://doi.org/10.1021/ol801092s
Publication status	Published - 17 Jul 2008

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title = "Electrophile-induced dearomatizing spirocyclization of N- arylisonicotinamides: A route to spirocyclic piperidines",

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.",

author = "Gareth Arnott and Heloise Brice and Jonathan Clayden and Emma Blaney",

year = "2008",

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doi = "10.1021/ol801092s",

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T1 - Electrophile-induced dearomatizing spirocyclization of N- arylisonicotinamides

T2 - A route to spirocyclic piperidines

AU - Arnott, Gareth

AU - Brice, Heloise

AU - Clayden, Jonathan

AU - Blaney, Emma

PY - 2008/7/17

Y1 - 2008/7/17

N2 - (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.

AB - (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.

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U2 - 10.1021/ol801092s

DO - 10.1021/ol801092s

M3 - Article (Academic Journal)

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AN - SCOPUS:52049096215

VL - 10

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EP - 3092

JO - Organic Letters

JF - Organic Letters

SN - 1523-7060

IS - 14

ER -

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

Abstract

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