The Forgotten Pyrazines: Exploring the Dakin-West Reaction.

The Forgotten Pyrazines: Exploring the Dakin-West Reaction.
Chemistry. 2020 Mar 26;:
Authors: Orru R, Wurdemann M, Niţu C, De Wildemann S, Bernaerts K
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 we explore access to pyrazines obtained from amino acids using the 90 year old Dakin-West reaction. After a qualitative screening several functional proteinogenic amino acids proved good substrates for this reaction, which were successfully scaled to multigram scale production of the corresponding intermediate α-acetamido ketones. Subsequently, we optimized the conditions towards pyrazine formation using δ-amino-levulinic acid, these were employed to synthesize a relevant set of five functional dimethylpyrazines. 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.
PMID: 32216072 [PubMed - as supplied by publisher]

Source: Chemistry - March 25, 2020 Category: Chemistry Authors: Orru R, Wurdemann M, Niţu C, De Wildemann S, Bernaerts K Tags: Chemistry Source Type: research