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Issue 22, 2019
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A niobium-catalyzed coupling reaction of α-keto acids with ortho-phenylenediamines: synthesis of 3-arylquinoxalin-2(1H)-ones

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Abstract

A general methodology to access valuable 3-arylquinoxalin-2(1H)-ones was developed, by the reaction of α-keto acids with ortho-phenylenediamines in the presence of ammonium niobium oxalate (ANO) as a catalyst. The reactions were conducted in only 10 min under ultrasonic irradiation as an alternative energy source, affording water as the only co-product. A total of twenty-three different 3-arylquinoxalin-2(1H)-ones were selectively obtained in good to excellent yields by this atom-efficient protocol. Additionally, 1H–15N HMBC experiments were used to reveal the regioisomerism of the obtained products.

Graphical abstract: A niobium-catalyzed coupling reaction of α-keto acids with ortho-phenylenediamines: synthesis of 3-arylquinoxalin-2(1H)-ones

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Publication details

The article was received on 29 Jul 2019, accepted on 10 Oct 2019 and first published on 11 Oct 2019


Article type: Paper
DOI: 10.1039/C9GC02662B
Green Chem., 2019,21, 6154-6160

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    A niobium-catalyzed coupling reaction of α-keto acids with ortho-phenylenediamines: synthesis of 3-arylquinoxalin-2(1H)-ones

    C. Ebersol, N. Rocha, F. Penteado, M. S. Silva, D. Hartwig, E. J. Lenardão and R. G. Jacob, Green Chem., 2019, 21, 6154
    DOI: 10.1039/C9GC02662B

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