Tandem Wolff rearrangement-“tert-amino effect” sequence: Synthesis of 2-oxoindolinium enolate derivatives
作者:Françoise Léost、Bernard Chantegrel、Christian Deshayes
DOI:10.1016/s0040-4020(97)00448-1
日期:1997.6
derivatives 4 through Wolff rearrangement and interaction of the tert-amino moiety with the ketene functionality. Variable amounts of either ammonium ylides 5 or of products resulting from their transformations were also formed during the course of the reaction. If the amino moiety was substituted by a benzyl or an allyl group, indolinones, resulting from [1,3] or [1,2] benzylic or allylic shifts,
1-重氮-2-氧代-(2- N,N-二取代的氨基苯基)乙基膦酸酯1的热解通过Wolff重排以及叔氨基部分与烯酮官能团的相互作用产生2-氧代吲哚鎓烯醇酸酯衍生物4 。在反应过程中还形成了不同量的叶立铵5或由其转化产生的产物。如果氨基部分被苄基或烯丙基取代,则分离由[1,3]或[1,2]苄基或烯丙基位移产生的吲哚酮取代化合物4和5。