亲电试剂诱导的N-芳基异烟酰胺的去芳构化螺环化反应：一条合成螺环哌啶的途径。
Electrophile-induced dearomatizing spirocyclization of N-arylisonicotinamides: a route to spirocyclic piperidines.
作者信息
Arnott Gareth, Brice Heloise, Clayden Jonathan, Blaney Emma
机构信息
School of Chemistry, University of Manchester, Manchester, UK.
出版信息
Org Lett. 2008 Jul 17;10(14):3089-92. doi: 10.1021/ol801092s. Epub 2008 Jun 14.
PMID:18553971
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.
摘要
用三氟甲磺酸酐处理N-芳基异烟酰胺会引发芳环对吡啶鎓中间体4-位的分子内亲核进攻。产物是螺环二氢吡啶，其可转化为与诸如MK-677等生物活性分子相关的有价值的螺环哌啶。
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