Solid-Phase and Solution-Phase Parallel Synthesis of Tetrahydro-isoquinolines via Pictet-Spengler Reaction

Authors: Sun Q.; Kyle D.J.

Source: Combinatorial Chemistry & High Throughput Screening, Volume 5, Number 1, February 2002 , pp. 75-81(3)

Publisher: Bentham Science Publishers

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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 percent yield. Both solution-phase and solid-phase synthesis of 6,7-dimethoxytetrahydroisoquinolines are described.

Keywords: Tetrahydro-isoquinolines; Pictet-Spengler Reaction; bischler-napieralski reaction

Language: English

Document Type: Review article

DOI: 10.2174/1386207023330624

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