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

Filipe Penteado; Marcelo M. Vieira; Gelson Perin; Diego Alves; Raquel G. Jacob; Claudio Santi; Eder J. Lenardão

doi:10.1039/C6GC02495E

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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†

Filipe Penteado,^a Marcelo M. Vieira,^a Gelson Perin,^a Diego Alves,^a Raquel G. Jacob,^a Claudio Santi^b and Eder J. Lenardão

*^a

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* Corresponding authors

^a Laboratório de Síntese Orgânica Limpa, LASOL, Universidade Federal de Pelotas, UFPel, P.O. Box 354, 96010-900 Pelotas, RS, Brazil
E-mail: lenardao@ufpel.edu.br
Tel: +55 (53) 3275-7533

^b Department of Pharmaceutical Sciences Group of Catalysis and Organic Green Chemistry – University of Perugia, Via del Liceo 1, 06100 Perugia, Italy

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.

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Article information

DOI: https://doi.org/10.1039/C6GC02495E
Article type: Paper
Submitted: 06 Sep 2016
Accepted: 16 Oct 2016
First published: 17 Oct 2016

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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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Green Chemistry

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†

Abstract

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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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