6533b835fe1ef96bd129f54e
RESEARCH PRODUCT
Synthesis of Pyrrolo[1,2-a]pyrimidine Enantiomers via Domino Ring-Closure followed by Retro Diels-Alder Protocol
Matti HaukkaMárta PalkóFerenc FülöpBeáta Feketesubject
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)description
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
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2017-04-01 | Molecules; Volume 22; Issue 4; Pages: 613 |