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Combinatorial liquid-phase synthesis of

Racker1, Doring, Reiser

  • 1Department of Organic Chemistry, University of Regensburg, Universitatsstrasse 31, D-93053 Regensburg, Germany.

The Journal of Organic Chemistry
|October 14, 2000
PubMed
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A novel Baylis-Hillman reaction method synthesizes [1,4]oxazepin-7-ones. Split synthesis on poly(ethylene glycol) (MeOPEG) efficiently screened substrate scope for this new chemical synthesis.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Medicinal Chemistry

Background:

  • Development of efficient synthetic routes for heterocyclic compounds is crucial in drug discovery.
  • [1,4]oxazepin-7-ones represent a class of heterocyclic compounds with potential biological activities.
  • The Baylis-Hillman reaction is a versatile carbon-carbon bond-forming reaction.

Purpose of the Study:

  • To develop a new synthetic method for [1,4]oxazepin-7-ones.
  • To utilize the Baylis-Hillman reaction as a key step in the synthesis.
  • To explore the scope and limitations of the developed synthetic method.

Main Methods:

  • A novel synthetic strategy employing the Baylis-Hillman reaction was designed.
  • A mixture library of [1,4]oxazepin-7-ones was synthesized using split synthesis on a soluble polymer support (poly(ethylene glycol) 5000 monomethyl ether, MeOPEG).

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  • Gas chromatography-electron ionization mass spectrometry (GC-EIMS) was used for library analysis, followed by parallel synthesis and full characterization of predominant products.

    • Main Results:

    • The developed method successfully synthesized [1,4]oxazepin-7-ones from readily available aldehydes and alpha-amino alcohols.
    • Split synthesis on MeOPEG proved to be an efficient approach for rapidly screening the substrate spectrum.
    • The scope and limitations of the reaction were determined through library synthesis and analysis.

    Conclusions:

    • A new, efficient synthetic route to [1,4]oxazepin-7-ones has been established.
    • Split synthesis on MeOPEG is a valuable tool for rapid substrate scope determination in new reaction development.
    • This methodology facilitates the exploration of diverse chemical space for potential therapeutic agents.