A NEW AND FACILE STEREOSELECTIVE SYNTHESIS OF<i>CIS</i>-4<i>a</i>-ARYL-1,2,3,4,4a,5,6,8<i>a</i>-OCTAHYDROISOQUINOLINE DERIVATIVES
作者:Shinzo Kano、Tsutomu Yokomatsu、Yoko Yuasa、Shiroshi Shibuya
DOI:10.1246/cl.1982.1915
日期:1982.12.5
Cis-1,2,3,4,4a,5,6,8a-octahydro-2-methyl-4a-phenylisoquinolin-3-one was obtained by cyclization of the acyliminium ion intermediate, derived from the corresponding amide. Reduction of this cyclization product with LiAlH4 in THF afforded cis-1,2,3,4,4a,5,6,8a-octahydro-2-methyl-4a-phenylisoquinoline. In a similar way, the octahydro-4a-(2-methoxyphenyl) isoquinolin-3-one was also prepared from the corresponding
Cis-1,2,3,4,4a,5,6,8a-octahydro-2-methyl-4a-phenylisoquinolin-3-one 通过环化来自相应酰胺的 acyliminium 离子中间体获得。在THF中用LiAlH4还原该环化产物得到顺式1,2,3,4,4a,5,6,8a-八氢-2-甲基-4a-苯基异喹啉。以类似的方式,八氢-4a-(2-甲氧基苯基)异喹啉-3-酮也由相应的酰胺制备。