Proline-derived azabicycloalkane amino acids are an important class of constrained dipeptide mimics. The presence of “easy-to-functionalize” chemical moieties onto their bicyclic core allows for the preparation of azabicycloalkane-based derivativ...
Artikel
Straightforward Access to Pyrazine‐(2,3)‐diones through Sequential Three‐Component Reaction
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A protocol for the assembly of polysubstituted 2,3-dioxo-1,4,5,6-tetrahydropyrazines and 2,3-dioxo-hydro-1H-cycloalkyl[b]pyrazines by the sequential reaction of primary aliphatic amines, 1,2-diaza-1,3-dienes and oxalyl chloride is reported. This approach represents an easy transformation of readily available precursors into target-relevant products difficult to obtain with alternative methods.
Abstract
A novel protocol for the assembly of polysubstituted 2,3-dioxo-1,4,5,6-tetrahydropyrazines and 2,3-dioxo-hydro-1H-cycloalkyl[b]pyrazines has been developed by the sequential three-component reaction of primary aliphatic amines, 1,2-diaza-1,3-dienes (DDs) and oxalyl chloride. This synthetic sequence proceeds by initial aza-Michael addition of the amine to the azo-ene compounds and subsequent ring closure involving the oxalyl chloride. The ready availability of the starting materials as well as the high level of practicability of the reaction and work-up make this approach an attractive opportunity towards these uncommon systems.
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