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Solid-phase and solution-phase parallel synthesis of tetrahydro-isoquinolines via Pictet-Spengler reaction
1Department of Computational, Combinatorial and Medicinal Chemistry, Purdue Pharma L.P., 6 Cedar Brook Drive, Cranbury, NJ 08512, USA.
Combinatorial Chemistry & High Throughput Screening
|February 28, 2002
Abstract:
An efficient parallel synthesis of 6,7-dimethoxytetrahydroisoquinolines is reported. The key reaction step is 3,4-dimethoxyphenethylimines reacting with acid chlorides to form an N-acyliminium ion intermediate, which undergoes Pictet-Spengler condensation to give the desired products in >80% yield. Both solution-phase and solid-phase synthesis of 6,7-dimethoxytetrahydroisoquinolines are described.