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A novel tandem Betti/Ullmann oxidation reaction as an efficient route for synthesis of new oxazepine derivatives

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Abstract

A novel tandem Betti/Ullmann/oxidation reaction was used for synthesis of new oxazepine derivatives containing kojic acid. This protocol includes a three-component Betti reaction of 2-naphthol, 2-haloanilines and kojic aldehyde followed by copper-mediated intramolecular Ullmann C-O coupling reaction and subsequently aerobic oxidation. This method provides a new and useful strategy for the construction of heterocycles. Also novel Betti bases based on kojic acid derivatives have been synthesized. In this regard, boric acid functionalized silica supported \(\hbox {Fe}_{3}\hbox {O}_{4}\) nanoparticle have been designed, synthesized and used as a highly efficient, environmentally benign and recyclable heterogeneous magnetic nanocatalyst for the direct synthesis of desired Betti bases under solvent free conditions.

Graphical Abstract

A novel tandem Betti/Ullmann/oxidation reaction was introduced for synthesis of new oxazepine derivatives. This method provides a new and useful strategy for the construction of heterocycles. In this regard, \(\hbox {Fe}_{3}\hbox {O}_{4}\)@\(\hbox {SiO}_{2}\)-boric acid nanoparticles have been synthesized and used for the synthesis of desired novel Betti bases based on kojic acid derivatives.

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Acknowledgements

The authors acknowledge the financial support from the Iran National Science Foundation (INSF) and University of Tabriz.

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Authors and Affiliations

  1. Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, P.O. Box 51666-16471, Tabriz, Iran

    Reza Teimuri-Mofrad, Mahdi Gholamhosseini-Nazari, Somayeh Esmati & Aziz Shahrisa

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  1. Reza Teimuri-Mofrad
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  2. Mahdi Gholamhosseini-Nazari
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  3. Somayeh Esmati
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  4. Aziz Shahrisa
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Correspondence to Reza Teimuri-Mofrad.

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Teimuri-Mofrad, R., Gholamhosseini-Nazari, M., Esmati, S. et al. A novel tandem Betti/Ullmann oxidation reaction as an efficient route for synthesis of new oxazepine derivatives. J Chem Sci 129, 1449–1459 (2017). https://doi.org/10.1007/s12039-017-1343-x

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