The Forgotten Pyrazines: Exploring the Dakin-West Reaction

Martien A. Wurdemann*, Cristina Nitu, Stefaan M. A. De Wildeman, Katrien V. Bernaerts*, Romano V. A. Orru*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Web of Science)

Abstract

Pyrazines are an underreported class of N-heterocycles available from nitrogen-rich biomass presenting an interesting functional alternative for current aromatics. In this work, access to pyrazines obtained from amino acids by using the 90 year old Dakin-West reaction was explored. After a qualitative screening several functional proteinogenic amino acids proved good substrates for this reaction, which were successfully scaled to multigram scale synthesis of the corresponding intermediate alpha-acetamido ketones. Subsequently, the conditions towards pyrazine formation using delta-amino-levulinic acid were optimized, and these were employed to synthesize a relevant set of five functional dimethylpyrazines in high purity. These pyrazines can be considered a versatile toolbox of aromatic building blocks for a wide range of applications, such as in the synthesis of polymers or metal-organic frameworks.

Original languageEnglish
Pages (from-to)8090-8100
Number of pages11
JournalChemistry: a European journal
Volume26
Issue number36
DOIs
Publication statusPublished - 26 Jun 2020

Keywords

  • amino acids
  • biobased building blocks
  • nitrogen heterocycles
  • radical ions
  • synthetic methods
  • 5-AMINOLEVULINIC ACID
  • GENERAL REACTION
  • INHIBITION
  • PLATFORM
  • BIOMASS

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