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Molecules 2005, 10(1), 226-237; doi:10.3390/10010226
Article

A Survey on the Reactivity of Phenyliodonium Ylide of 2-Hydroxy-1,4-Naphthoquinone with Amino Compounds

,  and *
Laboratory of Organic Chemistry, Chemistry Department, University of Thessaloniki, Thessaloniki 54124, Greece
* Author to whom correspondence should be addressed.
Received: 1 August 2004 / Accepted: 13 September 2004 / Published: 31 January 2005
(This article belongs to the Special Issue Hypervalent Iodine)
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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. Phenyliodonium ylides; 2-hydroxy-1; 4-naphthoquinone; aminoesters; ureas.
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Spagou, K.; Malamidou-Xenikaki, E.; Spyroudis, S. A Survey on the Reactivity of Phenyliodonium Ylide of 2-Hydroxy-1,4-Naphthoquinone with Amino Compounds. Molecules 2005, 10, 226-237.

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