Synthesis of novel N-heterocyclic compounds containing 1,2,3-triazole ring system via domino, “click” and RDA reactions

Márta Palkó, Mohamed El Haimer, Zsanett Kormányos, Ferenc Fülöp

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

An uncomplicated, high-yielding synthetic route has been developed to constitute complicated heterocycles, applying domino, click and retro-Diels–Alder (RDA) reaction sequences. Starting from 2-aminocarboxamides, a new set of isoindolo[2,1-a]quinazolinones was synthesized with domino ring closure. A click reaction was performed to create the 1,2,3-triazole heterocyclic ring, followed by an RDA reaction resulting in dihydropyrimido[2,1-a]isoindole-2,6-diones. The absolute configuration, concluded by the norbornene structure that served as a chiral source, remained constant throughout the transformations. The structure of the synthesized compounds was examined by1H and13C Nuclear Magnetic Resonance (NMR) methods.

Original languageEnglish
Article number772
JournalMolecules
Volume24
Issue number4
DOIs
Publication statusPublished - Feb 21 2019

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Keywords

  • Click reaction
  • Domino ring closure
  • RDA reaction
  • Regioselectivity
  • Stereoselectivity
  • Traceless chirality transfer

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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