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Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46
Graphical Abstract
Figure 1: Selected active pyrazinoisoquinolines, 2-oxopiperazines and aldose reductase inhibitors (ALR2).
Scheme 1: Comparison of previous reports with present work for piperazine-2,6-dione synthesis.
Scheme 2: Coupling of N-benzenesulfonyliminodiacetic acid with primary amines using CDI/DMAP.
Scheme 3: Formation of ene-diamides 9a–g and pyrazinones 10a–f.
Scheme 4: Mechanism for the formation of substituted pyrazinones.
Figure 2: HRMS spectra of aliquot generated from cyclization reaction of 7c.
Figure 3: ORTEP diagrams of compound 9b and 10a.
Scheme 5: Synthesis of 3-phenylpyrazinone.
Scheme 6: Synthesis of 4-N-benzyl-1-N-(aryl/heteroarylethyl)piperazine-2,6-dione.
Scheme 7: Cyclization of pyrazinoisoquinolines.
Scheme 8: Synthesis of the drug praziquantel 1.