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Combinatorial Chemistry & High Throughput Screening

Editor-in-Chief

ISSN (Print): 1386-2073
ISSN (Online): 1875-5402

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

Author(s): Qun Sun and Donald J. Kyle

Volume 5, Issue 1, 2002

Page: [75 - 81] Pages: 7

DOI: 10.2174/1386207023330624

Price: $65

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.

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


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