A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ3-Iodinane Compounds

Troian-Gautier, Ludovic;De Winter, Julien;Gerbaux, Pascal;Moucheron, Cécile
(2013) The Journal of Organic Chemistry — Vol. 78, n° 21, p. 11096-11101 (2013)

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Authors
  • Troian-Gautier, LudovicUCLouvain
    Author
  • De Winter, JulienUMons
    Author
  • Gerbaux, PascalUMons
    Author
  • Moucheron, CécileULB
    Author
Abstract
An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture. This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chemistry.
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Troian-Gautier, L., De Winter, J., Gerbaux, P., & Moucheron, C. (2013). A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ3-Iodinane Compounds. The Journal of Organic Chemistry, 78(21), 11096-11101. https://doi.org/10.1021/jo401872e (Original work published 2013)