Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol

Beáta Fekete; Márta Palkó; Matti Haukka; Ferenc Fülöp

doi:10.3390/molecules22040613

Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol

Molecules. 2017 Apr 13;22(4):613. doi: 10.3390/molecules22040613.

Authors

Beáta Fekete¹, Márta Palkó², Matti Haukka³, Ferenc Fülöp^{4

5}

Affiliations

¹ Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, Szeged H-6720, Hungary. fekete.beata@pharm.u-szeged.hu.
² Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, Szeged H-6720, Hungary. palko@pharm.u-szeged.hu.
³ Department of Chemistry, University of Jyväskylä, FIN-40014 Turku, Finland. matti.o.haukka@jyu.fi.
⁴ Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, Szeged H-6720, Hungary. fulop@pharm.u-szeged.hu.
⁵ MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Eötvös utca 6, Szeged H-6720, Hungary. fulop@pharm.u-szeged.hu.

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.

Keywords: N-heterocycles; domino reactions; hydroxamic acid; microwave chemistry; retro Diels-Alder reaction.

MeSH terms

Chemistry Techniques, Synthetic*
Crystallography, X-Ray
Hydroxamic Acids / chemistry
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Pyrimidines / chemical synthesis*
Stereoisomerism

Substances

Hydroxamic Acids
Pyrimidines