Convenient synthesis of 1-aryl-9H-β-carboline-3-carbaldehydes and their transformation into dihydropyrimidinone derivatives by Biginelli reaction

Péter Ábrányi-Balogh, András Dancsó, Dávid Frigyes, Balázs Volk, György Keglevich, Mátyás Milen

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Abstract

In the present work, a practical synthesis of 1-aryl-β-carboline-3-carbaldehydes as versatile building blocks and their application in Biginelli reaction is reported. The starting material of the four-step synthesis is racemic tryptophan methyl ester. The procedure involves a Pictet-Spengler cyclization, a dehydrogenation, an ester reduction, and an alcohol oxidation step. The β-carboline-3-carbaldehydes were further transformed using a Biginelli reaction into derivatives containing a pharmacologically significant dihydropyrimidine ring at position-3.

Original languageEnglish
Pages (from-to)5711-5719
Number of pages9
JournalTetrahedron
Volume70
Issue number35
DOIs
Publication statusPublished - Sep 2 2014

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Keywords

  • Biginelli reaction
  • Dihydropyrimidines
  • Nitrogen heterocycles
  • β-Carbolines

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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