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

被引：40

作者：

Arnott, Gareth ^{[1
]}

Brice, Heloise ^{[1
]}

Clayden, Jonathan ^{[1
]}

Blaney, Emma ^{[2
]}

机构：

[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England

[2] GlaxoSmithKline, New Frontiers Sci Pk, Harlow CM19 5AW, Essex, England

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 14期

关键词：

D O I：

10.1021/ol801092s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：3089 / 3092

页数：4

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