A survey on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone with amino compounds.
The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield.
Spagou
Konstantina
K
Laboratory of Organic Chemistry, Chemistry Department, University of Thessaloniki, Thessaloniki 54124, Greece.
Malamidou-Xenikaki
Elizabeth
E
Spyroudis
Spyros
S
D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D008954:Models, Biological; D009285:Naphthoquinones / Q000737:chemistry*; D009861:Onium Compounds / Q000737:chemistry*
D000588:Amines; D006571:Heterocyclic Compounds; D009285:Naphthoquinones; D009861:Onium Compounds; C510883:phenyliodonium; C005090:lawsone