Patil Renukadevi, Li Wei, Ross Charles R, Kraka Elfi, Cremer Dieter, Mohler Michael L, Dalton James T, Miller Duane D
Department of Pharmaceutical Sciences, The University of Tennessee Health Science Center, 847 Monroe Avenue, Room 327, Memphis, TN 38163, USA.
Tetrahedron Lett. 2006 Jun 5;47(23):3941-3944. doi: 10.1016/j.tetlet.2006.03.154.
A novel 1,4-N-->O migration of a disubstituted phenyl ring was observed during N-methylation of a bicalutamide derivative, (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2-methylpropionamide, in the presence of CsF-Celite/acetonitrile and desilylation of (2S)-2-(tert-butyldimethylsilanyloxy)-N-(4-cyano-3-trifluoromethylphenyl)-3-(4-fluorophenoxy)-2,N-dimethylpropionamide in tetra-n-butylammonium fluoride/THF. Both NMR and X-ray analysis confirmed the structure of the 1,4-N-->O disubstituted phenyl ring migrated product.
在比卡鲁胺衍生物(2S)-2-(叔丁基二甲基硅烷氧基)-N-(4-氰基-3-三氟甲基苯基)-3-(4-氟苯氧基)-2-甲基丙酰胺的N-甲基化反应中，于CsF-硅胶/乙腈存在下，观察到二取代苯环发生了一种新型的1,4-N→O迁移；并且在四丁基氟化铵/四氢呋喃中，(2S)-2-(叔丁基二甲基硅烷氧基)-N-(4-氰基-3-三氟甲基苯基)-3-(4-氟苯氧基)-2,N-二甲基丙酰胺发生了去硅烷化反应。核磁共振(NMR)和X射线分析均证实了1,4-N→O二取代苯环迁移产物的结构。
