a survey on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone with amino compounds调查的反应性方面phenyliodonium 2-hydroxy-1,4-naphthoquinone与氨基化合物.pdfVIP

Molecules 2005, 10, 226-237 molecules ISSN 1420-3049 A Survey on the Reactivity of Phenyliodonium Ylide of 2- Hydroxy-1,4-Naphthoquinone with Amino Compounds Konstantina Spagou, Elizabeth Malamidou-Xenikaki and Spyros Spyroudis* Laboratory of Organic Chemistry, Chemistry Department, University of Thessaloniki, Thessaloniki 54124, Greece. Tel.: (+30) 2310-997833, Fax: (+30) 2310-997679 *Author to whom correspondence should be addressed; e-mail sspyr@chem.auth.gr Received: 1 July 2004 / Accepted: 13 July 2004 / Published: 31 January 2005 Abstract: 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. Keywords: Phenyliodonium ylides, 2-hydroxy-1,4-naphthoquinone, aminoesters, ureas. Introduction Quinones bearing hydroxy groups on the quinone ring represent an interesting class within the quinone family. A great variety of these hydroxyquinones are found in nature [1] and almost all of them exhibit some kind of biological activity. Synthesis and reaction patterns of hydroxyquinones have been reviewed [2]. One of the most interesting properties of hydroxyquinones is the easy formation of aryliodonium ylides