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A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3-b]pyrazines

Abstract : Ammonium bifluoride was efficiently used (at a 0.5 mol % loading) to catalyze the cyclocondensation between 1,2-arylenediamines and 1,2-dicarbonyl compounds at room temperature in methanol-water, affording quinoxalines and pyrido[2,3-b]pyrazines in excellent yields. Importantly, 2,8-disubstituted quinoxalines and 3-substituted pyrido[2,3-b]pyrazines were regioselectively formed by reacting aryl glyoxals with 3-methyl-1,2-phenylenediamine and 2,3-diaminopyridine, respectively. Analysis of the DFT reactivity indices allowed to explain the catalytic role of ammonium bifluoride.
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Submitted on : Thursday, December 31, 2015 - 3:05:12 PM
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Frédéric Lassagne, Floris Chevallier, Thierry Roisnel, Vincent Dorcet, Florence Mongin, et al.. A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3-b]pyrazines. SYNTHESIS, Georg Thieme Verlag, 2015, 47 (17), pp.2680-2689. ⟨10.1055/s-0034-1380678⟩. ⟨hal-01248104⟩

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