Solid-phase and solution-phase parallel synthesis of tetrahydro-isoquinolines via Pictet-Spengler reaction.
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.
Sun
Qun
Q
Department of Computational, Combinatorial and Medicinal Chemistry, Purdue Pharma L.P., 6 Cedar Brook Drive, Cranbury, NJ 08512, USA.
Kyle
Donald J
DJ
D002851:Chromatography, High Pressure Liquid; D007546:Isoquinolines / Q000138:chemical synthesis*; D019906:Nuclear Magnetic Resonance, Biomolecular; D012996:Solutions
D007546:Isoquinolines; D012996:Solutions