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

Frédéric Lassagne; Floris Chevallier; Thierry Roisnel; Vincent Dorcet; Florence Mongin; Luis R. Domingo

doi:10.1055/s-0034-1380678

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(17): 2680-2689
DOI: 10.1055/s-0034-1380678

paper

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

Frédéric Lassagne*

^aChimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, Université de Rennes 1-CNRS, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France eMail: frederic.lassagne@univ-rennes1.fr eMail: florence.mongin@univ-rennes1.fr

,

Floris Chevallier

^aChimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, Université de Rennes 1-CNRS, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France eMail: frederic.lassagne@univ-rennes1.fr eMail: florence.mongin@univ-rennes1.fr

,

Thierry Roisnel

^bCentre de Diffractométrie X, Institut des Sciences Chimiques de Rennes, UMR 6226, Université de Rennes 1-CNRS, Bâtiment 10B, Case 1003, Campus de Beaulieu, 35042 Rennes, France

,

Vincent Dorcet

^bCentre de Diffractométrie X, Institut des Sciences Chimiques de Rennes, UMR 6226, Université de Rennes 1-CNRS, Bâtiment 10B, Case 1003, Campus de Beaulieu, 35042 Rennes, France

,

Florence Mongin*

^aChimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, Université de Rennes 1-CNRS, Bâtiment 10A, Case 1003, Campus de Beaulieu, 35042 Rennes, France eMail: frederic.lassagne@univ-rennes1.fr eMail: florence.mongin@univ-rennes1.fr

,

Luis R. Domingo*

^cUniversidad de Valencia, Departamento de Química Orgánica, Dr. Moliner 50, 46100 Burjassot, Valencia, Spain eMail: domingo@utopia.uv.es

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Abstract

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Abstract

Ammonium bifluoride was efficiently used at a 0.5 mol% loading to catalyze the cyclocondensation of 1,2-arylenediamines with 1,2-dicarbonyl compounds at room temperature in methanol–water to give quinoxalines or 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 the reaction of arylglyoxals with 3-methylbenzene-1,2-diamine or pyridine-2,3-diamine, respectively. An analysis of the density functional theory reactivity indices explained the catalytic role of ammonium bifluoride.

Key words

quinoxalines - heterocycles - regioselectivity - catalysis - cyclizations

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Referenzen

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