Rearrangement of isoxazoline-5-spiro derivatives. part 4. Synthesis of medium size benzofused azaheterocycles
作者:Franca M. Cordero、Andrea Goti、Francesco De Sarlo、Antonio Guarna、Alberto Brandi
DOI:10.1016/s0040-4020(01)89118-3
日期:1989.1
Medium sized aza-heterocycles are obtained by sequential cycloaddition-rearrangement of C,N-diphenylnitrone (1) to methylenecyclopropane (2) or methylenecyclobutane (8) besides the common rearrangement products (mainly the pyridone 5 and the azepinone 10). Thus, the valuable 2,3,5,6-tetrahydro-2-phenyl-1-benzazocin-4(1H)-one (6) and 1,2,3,5,6,7-hexahydro-2-phenyl-4H-1- benzazonin-4-one (11) are produced
通过将C,N-二苯基硝酮(1)依次环加成重排至亚甲基环丙烷(2)或亚甲基环丁烷(8),除常见的重排产物(主要是吡啶酮5和氮杂环庚酮10)以外,还获得了中等大小的氮杂杂环。因此,有价值的2,3,5,6-四氢-2-苯基-1-苯并偶氮-4(1 H)-一(6)和1,2,3,5,6,7-六氢-2-苯基-4 ħ -1- benzazonin -4-酮(11)被直接地在N-芳基环上的二价基团的中间体14%和12%的产率生产respectively.Delocalization负责上的自由基偶联邻的碳原子芳香环。