%0 Journal Article %T A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3-b]pyrazines %+ Institut des Sciences Chimiques de Rennes (ISCR) %+ Universidad de Valencia %A Lassagne, Frédéric %A Chevallier, Floris %A Roisnel, Thierry %A Dorcet, Vincent %A Mongin, Florence %A Domingo, Luis R %< avec comité de lecture %@ 0039-7881 %J Synthesis: Journal of Synthetic Organic Chemistry %I Georg Thieme Verlag %V 47 %N 17 %P 2680-2689 %8 2015-05-19 %D 2015 %R 10.1055/s-0034-1380678 %K 3-b]pyrazines %K pyrido[2 %K quinoxalines %K regioselectivity %K ammonium bifluoride %K catalysis %K DFT reactivity indices %Z Chemical SciencesJournal articles %X 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. %G English %2 https://univ-rennes.hal.science/hal-01248104/document %2 https://univ-rennes.hal.science/hal-01248104/file/main%20quinox%20Mongin.pdf %L hal-01248104 %U https://univ-rennes.hal.science/hal-01248104 %~ UNIV-RENNES1 %~ CNRS %~ INSA-RENNES %~ ENSC-RENNES %~ ISCR %~ SCR-CD %~ SCR_CPM %~ UR1-SPM %~ ISCR-PRATS %~ INC-CNRS %~ UR1-UFR-SPM %~ UR1-HAL %~ ISCR-CORINT %~ UR1-SDLM %~ TEST-UNIV-RENNES %~ TEST-UR-CSS %~ UNIV-RENNES %~ INSA-GROUPE %~ ISCR-CORINT1 %~ UR1-MMS %~ ISCR-CORINT3 %~ TEST2-HALCNRS