Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 21, Issue 17, Pages 3604-3614Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d3ob00356f
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This article describes the efficient synthesis of novel nitroso-pyrazolylquinoxalines through regioselective cyclocondensation of 2-hydroxyimino-1,3-diketones with hydrazinylquinoxalines. The use of 2-hydroxyimino-1,3-diketones as electrophilic reagents in cyclocondensation with hetarylhydrazines is reported for the first time. The synthesis of nitroso-substituted pyrazolylquinoxalines was achieved in high yields using both one-pot and two-step procedures, and a gram-scale synthesis, as well as oxidation and reduction reactions, were successfully carried out.
This article describes the regioselective synthesis of novel nitroso-pyrazolylquinoxalines via cyclocondensation of 2-hydroxyimino-1,3-diketones with hydrazinylquinoxalines. Of note, this is the first time that 2-hydroxyimino-1,3-diketones are used as electrophilic reagents to cyclocondensation with hetarylhydrazines. The cyclocondensation proceeded through a hydrazone intermediates formation. A series of novel nitroso-substituted pyrazolylquinoxalines were synthesized by both one-pot and two-step procedures in up to 86% yields. Importantly, a gram-scale synthesis of nitroso-pyrazolylquinoxalines, their oxidation and reduction were successfully accomplished.
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