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

Research output: Contribution to journalArticle

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

Fingerprint

Isoindoles
Diels-Alder reactions
Enantiomers
enantiomers
Cycloaddition Reaction
chirality
carboxylates
closures
crystallography
Derivatives
microwaves
preparation
nuclear magnetic resonance
acids
Chirality
rings
X ray crystallography
X Ray Crystallography
Microwaves
configurations

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

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title = "A Domino Ring-Closure Followed by Retro-Diels-Alder Reaction for the Preparation of Pyrimido[2,1-a]isoindole Enantiomers",
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.",
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T1 - A Domino Ring-Closure Followed by Retro-Diels-Alder Reaction for the Preparation of Pyrimido[2,1-a]isoindole Enantiomers

AU - Fekete, Beáta

AU - Palkó, Márta

AU - Mándity, I.

AU - Haukka, Matti

AU - Fülöp, F.

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

KW - Chiral resolution

KW - Domino reactions

KW - Microwave chemistry

KW - Nitrogen heterocycles

KW - Synthetic methods

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