Efficient Synthesis of Novel 1-Substituted β- Carboline Derivatives via Pictet-Spengler Cyclization of 5-Hydroxy-L-Tryptophan

Nur Ain Nabilah Ashari; Noor Hidayah Pungot; Nor Akmalazura Jani; Zurina  Shaameri

doi:10.11113/mjfas.v18n2.2331

Authors

Nur Ain Nabilah Ashari Organic Synthesis Laboratory, Institute of Science, Universiti Teknologi MARA Puncak Alam, 43200 Bandar Puncak Alam, Selangor, Malaysia
Noor Hidayah Pungot Organic Synthesis Laboratory, Institute of Science, Universiti Teknologi MARA Puncak Alam, 43200 Bandar Puncak Alam, Selangor, Malaysia
Nor Akmalazura Jani Faculty of Applied Sciences, Universiti Teknologi MARA, 72000 Kuala Pilah, Negeri Sembilan, Malaysia
Zurina Shaameri Organic Synthesis Laboratory, Institute of Science, Universiti Teknologi MARA Puncak Alam, 43200 Bandar Puncak Alam, Selangor, Malaysia

DOI:

https://doi.org/10.11113/mjfas.v18n2.2331

Keywords:

Pictet-Spengler condensation, Wolff-Kishner reaction, β-carbolines, 5-hydroxy-L-tryptophan

Abstract

A facile synthesis of novel 1-substituted β-carboline derivatives by using three efficient reaction steps was described. The synthetic route began with the construction of β-carboline frameworks involving the coupling of 5-hydroxy-L-tryptophan with different substituted phenylglyoxal via Pictet-Spengler condensation. Subsequent reduction of carbonyl functionality on carbon-7’ by using Wolff-Kishner reaction followed by N-alkylation afforded a practical access to a series of 1-substituted β-carboline derivatives in moderate yields. These novel derivatives were successfully synthesized without the use of expensive metal catalyst, prolonged reaction hours or critical reaction conditions. The molecular structures of all synthesized derivatives were confirmed by infrared (IR), gas chromatography–mass spectrometry (GC-MS) and nuclear magnetic resonance (NMR) spectroscopy.

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