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Paper | Regular issue | Vol 65, No. 5, 2005, pp.1063-1069
Published online, 24th March, 2005
DOI: 10.3987/COM-05-10336
Synthesis of Functionalized Tetrahydro-β-carboline Derivatives by Modified Pictet-Spengler Reaction

Donghong Li, Yongbin Zhang, Wei Guo,* and Chizhong Xia*

*School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, China

Abstract

Instead of iminium salt in Pictet-Spengler reaction, a series of indole-bearing secondary enamines were synthesized through one-carbon unit transfer reactions of a tetrahydrofolate coenzyme models with tryptamine, and applied to Pictet-Spengler reaction. Reaction of the secondary enamines in acid conditions produced a series of functionalized tetrahydro-β-carboline derivatives in good to excellent yields.