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Molecules 2017, 22(4), 613; doi:10.3390/molecules22040613

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

1
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös utca 6, Szeged H-6720, Hungary
2
Department of Chemistry, University of Jyväskylä, FIN-40014 Turku, Finland
3
MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Eötvös utca 6, Szeged H-6720, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Rafael Chinchilla
Received: 10 March 2017 / Revised: 4 April 2017 / Accepted: 6 April 2017 / Published: 13 April 2017
(This article belongs to the Special Issue Asymmetric Synthesis 2017)
View Full-Text   |   Download PDF [1910 KB, uploaded 13 April 2017]   |  

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. View Full-Text
Keywords: domino reactions; hydroxamic acid; microwave chemistry; N-heterocycles; retro Diels-Alder reaction domino reactions; hydroxamic acid; microwave chemistry; N-heterocycles; retro Diels-Alder reaction
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Fekete, B.; Palkó, M.; Haukka, M.; Fülöp, F. Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol. Molecules 2017, 22, 613.

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