Synthesis of pyrrolo[1,2-a]pyrimidine enantiomers via domino ring-closure followed by retro Diels-Alder protocol

Beáta Fekete, Márta Palkó, Matti Haukka, F. Fülöp

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

From 2-aminonorbornene hydroxamic acids, a simple and efficient method for the preparation of pyrrolo[1,2-a]pyrimidine enantiomers is reported. The synthesis is based on domino ring-closure followed by microwave-induced retro Diels-Alder (RDA) protocols, where the chirality of the desired products is transferred from norbornene derivatives. The stereochemistry of the synthesized compounds was proven by X-ray crystallography. The absolute configuration of the product is determined by the configuration of the starting amino hydroxamic acid.

Original languageEnglish
Article number613
JournalMolecules
Volume22
Issue number4
DOIs
Publication statusPublished - Apr 1 2017

Fingerprint

Hydroxamic Acids
Enantiomers
enantiomers
pyrimidines
closures
Stereochemistry
Chirality
rings
X ray crystallography
X Ray Crystallography
stereochemistry
synthesis
products
Microwaves
configurations
chirality
crystallography
amino acids
Amino acids
Derivatives

Keywords

  • Domino reactions
  • Hydroxamic acid
  • Microwave chemistry
  • N-heterocycles
  • Retro Diels-Alder reaction

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of pyrrolo[1,2-a]pyrimidine enantiomers via domino ring-closure followed by retro Diels-Alder protocol. / Fekete, Beáta; Palkó, Márta; Haukka, Matti; Fülöp, F.

In: Molecules, Vol. 22, No. 4, 613, 01.04.2017.

Research output: Contribution to journalArticle

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