A novel isocyanide-based three-component reaction: synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives.
A novel multi-component synthesis of highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives starting from simple and readily available inputs is described. Thus, simply stirring an ethanol solution of 2,3-diaminomaleonitrile, a ketone, and an isocyanide in the presence of a catalytic amount of p-toluenesulfonic acid provided highly substituted 1,6-dihydropyrazine-2,3-dicarbonitrile derivatives in good to excellent yields at ambient temperature.
Shaabani
Ahmad
A
Department of Chemistry, Shahid Beheshti University, P.O. Box 19396-4716, Tehran, Iran. a-shaabani@cc.sbu.ac.ir
Maleki
Ali
A
Moghimi-Rad
Jafar
J
D000447:Aldehydes / Q000737:chemistry; D001557:Benzenesulfonates / Q000737:chemistry; D002625:Chemistry, Organic / Q000379:methods*; D002855:Chromatography, Thin Layer; D003486:Cyanides / Q000737:chemistry*; D000431:Ethanol / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry*
C523085:1,6-dihydropyrazine-2,3-dicarbonitrile; D000447:Aldehydes; D001557:Benzenesulfonates; D003486:Cyanides; D009570:Nitriles; D011719:Pyrazines; D000431:Ethanol; C029501:4-toluenesulfonic acid