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RESEARCH PRODUCT
A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3-b]pyrazines
Vincent DorcetFloris ChevallierLuis R. DomingoFrédéric LassagneThierry RoisnelFlorence Monginsubject
010405 organic chemistryChemistryOrganic ChemistryRegioselectivityAmmonium bifluoride010402 general chemistrypyrido[201 natural sciencesCatalysisammonium bifluoride0104 chemical sciencesCatalysischemistry.chemical_compoundregioselectivity3-b]pyrazinesDFT reactivity indices[CHIM]Chemical SciencesOrganic chemistryquinoxalinesDensity functional theoryReactivity (chemistry)description
International audience; 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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2015-05-19 | Synthesis |