کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5221574 | 1383424 | 2010 | 7 صفحه PDF | دانلود رایگان |
New synthetic equivalents, N-methoxy-N-methyl-Nâ²-phenylsulfonyl glycinamide and N-methoxy-N-methyl-Nâ²-benzyl-Nâ²-tert-butyloxy carbonyl glycinamide based on WA functionality were developed for the convenient synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinoline framework. Two simple reactions, N-benzylation and addition of arylmagnesium halide on the WA functionality of the former afforded the key intermediate for convenient synthesis of N-phenylsulfonyl protected 4-aryl-1,2,3,4-tetrahydroisoquinoline, through reduction and acid promoted cyclization. With the latter, the addition of arylmagnesium halide on the WA functionality followed by the same protocol afforded the direct synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines in good yields. The acid promoted cyclization step enabled concomitant removal of N-Boc protection.
Journal: Tetrahedron - Volume 66, Issue 21, 22 May 2010, Pages 3723-3729