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The Forgotten Pyrazines: Exploring the Dakin–West Reaction
Author(s) -
Würdemann Martien A.,
Niţu Cristina,
De Wildeman Stefaan M. A.,
Bernaerts Katrien V.,
Orru Romano V. A.
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000475
Subject(s) - pyrazine , chemistry , organic chemistry , amino acid , levulinic acid , combinatorial chemistry , nitrogen , catalysis , biochemistry
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 α‐acetamido ketones. Subsequently, the conditions towards pyrazine formation using δ‐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.