Synthetic study on the T3P®-promoted one-pot preparation of 1-substituted-3,4-dihydro-β-carbolines by the reaction of tryptamine with carboxylic acids

Péter Ábrányi-Balogh, Tamás Földesi, A. Grün, Balázs Volk, G. Keglevich, Mátyás Milen

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Abstract

A novel and efficient one-pot method has been developed for the synthesis of 1-substituted-3,4-dihydro-β-carbolines from tryptamine and a wide variety of carboxylic acids. The reaction was successfully applied to the synthesis of an important alkaloid harmalan as well as dihydro-eudistomin-U. This represents the first case in which 1-propanephosphonic acid cyclic anhydride (T3P®) has been used in the Bischler-Napieralski reaction. Unexpectedly it was observed that less than two equivalents of the T3P® reagent were sufficient for the two consecutive reactions.

Original languageEnglish
Pages (from-to)1953-1957
Number of pages5
JournalTetrahedron Letters
Volume57
Issue number18
DOIs
Publication statusPublished - May 4 2016

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Keywords

  • Bischler-Napieralski reaction
  • One-pot synthesis
  • Ring closure
  • T3P®
  • β-Carbolines

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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