Comparative evaluation of a Pictet-Spengler protocol in microwave-assisted conversions of tryptamine with aryl- and carboxyaryl aldehydes: Role of ring strain in cyclocondensation of the primarily formed carboxyaryl-substituted β-carbolines

Kinga Judit Fodor, Vasile Ludovic Kocsis, Kolos Kiss, Benedek Imre Károlyi, Ármin Szabolcs, Luminita Silaghi-Dumitrescu, Antal Csámpai

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

An efficient microwave-assisted Pictet-Spengler protocol employing boric acid/acetic acid as a catalytic system was elaborated for the synthesis of 1-aryl-β-carbolines. Under the novel conditions tryptamine and 2-formylbenzoic acid furnished a pentacyclic skeleton in a single step, whereas using o-phthalaldehyde as a coupling partner led to the formation of an isoindolone derivative. Three β-carbolines primarily resulted from the reactions involving carboxy-substituted heteroaryl aldehydes and avoided cyclisation to polycondensed skeletons with enhanced ring strain, as was evidenced by density functional theory (DFT) modelling.

Original languageEnglish
Pages (from-to)1381-1387
Number of pages7
JournalMonatshefte fur Chemie
Volume144
Issue number9
DOIs
Publication statusPublished - Sep 1 2013

Keywords

  • Anticancer
  • Catalysis
  • DFT calculations
  • Improved methods
  • Microwave irradiation
  • Pictet-Spengler

ASJC Scopus subject areas

  • Chemistry(all)

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