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...

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Bibliographic Details
Main Authors: Fekete Beáta
Palkó Márta
Mándity István M.
Haukka Matti
Fülöp Ferenc
Format: Article
Published: Wiley-VCH 2016
Series:EUROPEAN JOURNAL OF ORGANIC CHEMISTRY 2016 No. 21
doi:10.1002/ejoc.201600434

mtmt:3107753
Online Access:http://publicatio.bibl.u-szeged.hu/9896
Description
Summary: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.
Physical Description:3519-3527
ISSN:1434-193X