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 microwa...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
Wiley-VCH
2016
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| Sorozat: | EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
2016 No. 21 |
| doi: | 10.1002/ejoc.201600434 |
| mtmt: | 3107753 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/9896 |
| Tartalmi kivonat: | 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 (3)J(H,H) coupling constants] and X-ray crystallography. |
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| Terjedelem/Fizikai jellemzők: | 3519-3527 |
| ISSN: | 1434-193X |