0000000000821754
AUTHOR
Beáta Fekete
Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
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. peerReviewed
A Domino Ring‐Closure Followed by Retro‐Diels–Alder Reaction for the Preparation of Pyrimido[2,1‐ a ]isoindole Enantiomers
A simple method was developed to prepare pyrimido[2,1-a]isoindole derivatives by using di-endo- and di-exo-ethyl 3-aminobicyclo[2.2.1]hept-5-ene-2-carboxylate enantiomers as chiral sources. The method is based on a domino ring-closure reaction of norbornene 2-aminohydroxamic acid followed by microwave-induced retro-Diels–Alder reaction. In the case of enantiomeric starting substances, the chirality is transferred from norbornene derivatives to pyrimido[2,1-a]isoindoles. The configurations of the synthesized compounds were determined by 1D and 2D NMR spectroscopy [based on 2D NOE cross-peaks and 3JH,H coupling constants] and X-ray crystallography.
CCDC 1456785: Experimental Crystal Structure Determination
Related Article: Beáta Fekete, Márta Palkó, István Mándity, Matti Haukka, Ferenc Fülöp|2016|Eur.J.Org.Chem.|2016|3519|doi:10.1002/ejoc.201600434
CCDC 1508564: Experimental Crystal Structure Determination
Related Article: Beáta Fekete, Márta Palkó, Matti Haukka, Ferenc Fülöp|2017|Molecules|22|613|doi:10.3390/molecules22040613
CCDC 1508563: Experimental Crystal Structure Determination
Related Article: Beáta Fekete, Márta Palkó, Matti Haukka, Ferenc Fülöp|2017|Molecules|22|613|doi:10.3390/molecules22040613
CCDC 1508562: Experimental Crystal Structure Determination
Related Article: Beáta Fekete, Márta Palkó, Matti Haukka, Ferenc Fülöp|2017|Molecules|22|613|doi:10.3390/molecules22040613
CCDC 1456786: Experimental Crystal Structure Determination
Related Article: Beáta Fekete, Márta Palkó, István Mándity, Matti Haukka, Ferenc Fülöp|2016|Eur.J.Org.Chem.|2016|3519|doi:10.1002/ejoc.201600434