Mild Amination of Azoles

  • Author: ChemViews
  • Published Date: 23 November 2010
  • Source / Publisher: Angewandte Chemie International Edition/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Mild Amination of Azoles

Nitrogen containing molecules are of great interest in the biological, pharmaceutical and materials sciences, so the controlled and catalyzed introduction of a nitrogen atom into a synthetic target has undergone much research.

Sukbok Chang and co-workers, Korea Advanced Institute of Science and Technology, Republic of Korea, have examined the amination of azoles in the presence of a peroxide-based oxidant, a Brønsted acid and cobalt or manganese acetate. By using these conditions, the direct amination of benzoxazoles could be carried out at room temperature, with low catalyst loadings (2 mol%), to afford a range of 2-aminated products.

From kinetic isotope effects and isolation of amidine compounds, the authors propose the in situ formation of alkoxy and alkylperoxy radicals, each of which abstracts a hydrogen atom from the 2-aminobenzoxazolidine intermediate to produce the 2-aminobenzoxazole product.

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