Harikrishna Kommidi, Sivaraman Balasubramaniam, I. Aidhen
May 22, 2010
Citations
0
Influential Citations
10
Citations
Journal
Tetrahedron
Abstract
Abstract New synthetic equivalents, N -methoxy- N -methyl- N ′-phenylsulfonyl glycinamide and N -methoxy- N -methyl- N ′-benzyl- N ′- 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.