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, F. Fülöp

Research output: Contribution to journalArticle

1 Citation (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 by 1 H and 13 C Nuclear Magnetic Resonance (NMR) methods.

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

Fingerprint

Isoindoles
Quinazolinones
Heterocyclic Compounds
heterocyclic compounds
Triazoles
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
rings
synthesis
Dione
closures
routes
nuclear magnetic resonance
configurations
2-norbornene

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

Cite this

Synthesis of novel N-heterocyclic compounds containing 1,2,3-triazole ring system via domino, “click” and RDA reactions. / Palkó, Márta; Haimer, Mohamed El; Kormányos, Zsanett; Fülöp, F.

In: Molecules, Vol. 24, No. 4, 772, 21.02.2019.

Research output: Contribution to journalArticle

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