Preparation of 1-substituted-3,4-dihydronaphthalene-2-carboxaldehyde N,N-dimethylhydrazones by palladium(0) coupling, and their electrocyclic ring closure
作者:Thomas L. Gilchrist、Maureen A.M. Healy
DOI:10.1016/s0040-4020(01)86333-x
日期:1993.3
involving halogen-metal exchange and palladium(0) catalysed cross coupling, into N,N-dimethylhydrazones of 1-aryl- and 1-vinyl-3,4-dihydronaphthalene-2- carboxaldehydes. The N,N-dimethylhydrazone 10 of the aldehyde 2 undergoes efficient bromine-lithium exchange with butyllithium, as does 2-bromobenzaldehyde N,N-dimethylhydrazone 17. The dimethylhydrazones of 1-vinyl-3,4-dihydronaphthalene-2-carboxaldehydes
1-溴-3,4-二氢萘-2-甲醛2已通过三种方法转化,分别涉及卤素-金属交换和钯(0)催化的交叉偶联,转化为1-芳基和1-的N,N-二甲基hydr乙烯基-3,4-二氢萘-2-甲醛。的N,N- -dimethylhydrazone 10醛的2所与丁基锂经历高效溴-锂交换,象2-溴苯甲醛-N,N- -dimethylhydrazone 17。的1-乙烯基-3,4-二氢化萘-2-羧醛的dimethylhydrazones不是由后行电环环闭合,随后在溶液中二甲胺的损失,得到5,6-二氢苯并〔分离˚F]异喹啉。当进行气相热解时, 1-芳基-3,4-二氢萘-2-羧醛N,N-二甲基hydr也以相同的方式环化。