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Issue 24, 2016
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Niobium-promoted reaction of α-phenylglyoxylic acid with ortho-functionalized anilines: synthesis of 2-arylbenzothiazoles and 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones

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Abstract

A new and general method to prepare 2-arylbenzothiazoles and 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones by the reaction of α-arylglyoxylic acid with o-aminothiophenol and o-aminophenol respectively is described. The use of ammonium niobium oxalate (ANO) as the catalyst and PEG-400 as the solvent were crucial to afford the title compounds in good yields and selectivity. The reaction time can be reduced from hours to few minutes when ultrasound is used as an alternative energy source.

Graphical abstract: Niobium-promoted reaction of α-phenylglyoxylic acid with ortho-functionalized anilines: synthesis of 2-arylbenzothiazoles and 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones

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Publication details

The article was received on 06 Sep 2016, accepted on 16 Oct 2016 and first published on 17 Oct 2016


Article type: Paper
DOI: 10.1039/C6GC02495E
Citation: Green Chem., 2016,18, 6675-6680
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    Niobium-promoted reaction of α-phenylglyoxylic acid with ortho-functionalized anilines: synthesis of 2-arylbenzothiazoles and 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones

    F. Penteado, M. M. Vieira, G. Perin, D. Alves, R. G. Jacob, C. Santi and E. J. Lenardão, Green Chem., 2016, 18, 6675
    DOI: 10.1039/C6GC02495E

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