A new efficient synthetic methodology for tetrahydroisoquinoline and tetrahydro-beta-carboline derivatives using the Pictet-Spengler reaction

Mol Divers. 2004;8(4):427-30. doi: 10.1023/b:modi.0000047505.29920.35.

Abstract

A new solution-phase methodology microwave-assisted for improving the Pictet-Spengler reaction in the synthesis of the tetrahydroisoquinoline and beta-carboline derivatives has been reported. This methodology was applied to obtain a small library of tetrahydroisoquinoline and beta-carboline derivatives using L-Dopa, dopamine, and tryptophan, as well as a variety of commercially available aldehydes as starting material. The use of such nonconventional reaction conditions reveals several features like a short reaction time compared to conventional eating, ease of isolation of the products after work-up, and improvement of the yields. This new one-pot protocol would be an ideal and rapid method to synthesize compounds in a combinatorial context.

MeSH terms

  • Carbolines / chemical synthesis*
  • Carbolines / chemistry*
  • Combinatorial Chemistry Techniques*
  • Dopamine / chemistry
  • Levodopa / chemistry
  • Magnetic Resonance Spectroscopy
  • Microwaves
  • Models, Chemical
  • Tetrahydroisoquinolines / chemical synthesis*
  • Tetrahydroisoquinolines / chemistry*
  • Time Factors
  • Tryptophan / chemistry

Substances

  • Carbolines
  • Tetrahydroisoquinolines
  • Levodopa
  • tryptoline
  • Tryptophan
  • Dopamine