A Domino Ring-Closure Followed by Retro-Diels-Alder Reaction for the Preparation of Pyrimido[2,1-a]isoindole Enantiomers

Beáta Fekete, Márta Palkó, I. Mándity, Matti Haukka, F. Fülöp

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8 Citations (Scopus)

Abstract

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.

Original languageEnglish
JournalEuropean Journal of Organic Chemistry
DOIs
Publication statusAccepted/In press - 2016

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Keywords

  • Chiral resolution
  • Domino reactions
  • Microwave chemistry
  • Nitrogen heterocycles
  • Synthetic methods

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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