A novel palladium-catalyzed synthesis of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones.
Reactions of enamines, derived from 2-nitroanilines and alpha-substituted aldehydes, with carbon monoxide (6 atm) in the presence of a catalytic amount of bis(dibenzylideneacetone)palladium(0) (Pd(dba)(2)) and 1,3-bis(diphenylphosphino)propane (dppp) afford readily separated mixtures of 1,2-dihydroquinoxalines and 3,4-dihydroquinoxalinones. Addition of a catalytic amount of 1,10-phenanthroline to the reaction mixture substantially improved the yield of products. [reaction: see text]
Söderberg
Björn C G
BC
Department of Chemistry, West Virginia University, Morgantown, WV 26506-6045, USA. bjorn.soderberg@mail.wvu.edu
Wallace
Jeffery M
JM
Tamariz
Joaquín
J
D002248:Carbon Monoxide / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D011810:Quinoxalines / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D011810:Quinoxalines; D010165:Palladium; D002248:Carbon Monoxide