Solid-phase and solution-phase parallel synthesis of tetrahydro-isoquinolines via Pictet-Spengler reaction

Comb Chem High Throughput Screen. 2002 Feb;5(1):75-81. doi: 10.2174/1386207023330624.

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.

Publication types

  • Comparative Study

MeSH terms

  • Chromatography, High Pressure Liquid
  • Isoquinolines / chemical synthesis*
  • Nuclear Magnetic Resonance, Biomolecular
  • Solutions

Substances

  • Isoquinolines
  • Solutions