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RESEARCH PRODUCT
A Domino Ring‐Closure Followed by Retro‐Diels–Alder Reaction for the Preparation of Pyrimido[2,1‐ a ]isoindole Enantiomers
Ferenc FülöpFerenc FülöpMárta PalkóBeáta FeketeMatti HaukkaIstván M. Mánditysubject
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)ta116Norbornenedescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2016-06-24 | European Journal of Organic Chemistry |