0000000000821754

AUTHOR

Beáta Fekete

showing 7 related works from this author

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

2017

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

Models MolecularMagnetic Resonance SpectroscopyPyrimidinehydroxamic acidStereochemistryPharmaceutical ScienceChemistry Techniques SyntheticCrystallography X-RayHydroxamic Acids010402 general chemistryRing (chemistry)01 natural sciencesArticleDominoAnalytical Chemistrymicrowave chemistrylcsh:QD241-441chemistry.chemical_compoundlcsh:Organic chemistryDrug DiscoveryPhysical and Theoretical ChemistryN-heterocyclesta116Norbornenedomino reactions; hydroxamic acid; microwave chemistry; <i>N</i>-heterocycles; retro Diels-Alder reactionHydroxamic acidMolecular Structure010405 organic chemistryretro Diels-Alder reactionOrganic Chemistrydomino reactionsAbsolute configurationStereoisomerism0104 chemical sciencesPyrimidineschemistryChemistry (miscellaneous)Molecular MedicineEnantiomerChirality (chemistry)Molecules; Volume 22; Issue 4; Pages: 613
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A Domino Ring‐Closure Followed by Retro‐Diels–Alder Reaction for the Preparation of Pyrimido[2,1‐ a ]isoindole Enantiomers

2016

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.

Isoindoles010405 organic chemistryStereochemistryChemistrydomino reactionsOrganic Chemistry010402 general chemistryRing (chemistry)Retro-Diels–Alder reaction01 natural sciencesMedicinal chemistryChiral resolutionmicrowave chemistry0104 chemical scienceschemistry.chemical_compoundsynthetic methodschiral resolutionnitrogen heterocyclesPhysical and Theoretical ChemistryEnantiomerIsoindoleChirality (chemistry)ta116NorborneneEuropean Journal of Organic Chemistry
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CCDC 1456785: Experimental Crystal Structure Determination

2016

Related Article: Beáta Fekete, Márta Palkó, István Mándity, Matti Haukka, Ferenc Fülöp|2016|Eur.J.Org.Chem.|2016|3519|doi:10.1002/ejoc.201600434

12-hydroxy-312-diazapentacyclo[13.2.1.0214.0311.0510]octadeca-57916-tetraene-413-dione monohydrateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1508564: Experimental Crystal Structure Determination

2017

Related Article: Beáta Fekete, Márta Palkó, Matti Haukka, Ferenc Fülöp|2017|Molecules|22|613|doi:10.3390/molecules22040613

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters8-methoxy-7-methyl-38-diazatetracyclo[9.2.1.0210.037]tetradec-12-ene-49-dioneExperimental 3D Coordinates
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CCDC 1508563: Experimental Crystal Structure Determination

2017

Related Article: Beáta Fekete, Márta Palkó, Matti Haukka, Ferenc Fülöp|2017|Molecules|22|613|doi:10.3390/molecules22040613

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersmethyl 8-methoxy-49-dioxo-38-diazatetracyclo[9.2.1.0210.037]tetradec-12-ene-7-carboxylateExperimental 3D Coordinates
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CCDC 1508562: Experimental Crystal Structure Determination

2017

Related Article: Beáta Fekete, Márta Palkó, Matti Haukka, Ferenc Fülöp|2017|Molecules|22|613|doi:10.3390/molecules22040613

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersmethyl 8-methoxy-49-dioxo-38-diazatetracyclo[9.2.1.0210.037]tetradec-12-ene-7-carboxylateExperimental 3D Coordinates
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CCDC 1456786: Experimental Crystal Structure Determination

2016

Related Article: Beáta Fekete, Márta Palkó, István Mándity, Matti Haukka, Ferenc Fülöp|2016|Eur.J.Org.Chem.|2016|3519|doi:10.1002/ejoc.201600434

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parametersethyl 3-(((1-phenylethyl)carbamoyl)amino)bicyclo[2.2.1]hept-5-ene-2-carboxylateExperimental 3D Coordinates
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