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Raw SA, Wilfred CD, Taylor RJ. Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Org Biomol Chem. 2004;2(5):788-96doi: 10.1039/b315689c.
Raw, S. A., Wilfred, C. D., & Taylor, R. J. (2004). Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Organic & biomolecular chemistry, 2(5), 788-96. https://doi.org/10.1039/b315689c
Raw, Steven A, et al. "Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds." Organic & biomolecular chemistry vol. 2,5 (2004): 788-96. doi: https://doi.org/10.1039/b315689c
Raw SA, Wilfred CD, Taylor RJ. Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds. Org Biomol Chem. 2004 Mar 07;2(5):788-96. doi: 10.1039/b315689c. Epub 2004 Feb 11. PMID: 14985820.
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Org Biomol Chem. 2004 Mar 07;2(5):788-96. doi: 10.1039/b315689c. Epub 2004 Feb 11.

Tandem oxidation processes for the preparation of nitrogen-containing heteroaromatic and heterocyclic compounds.

Organic & biomolecular chemistry

Steven A Raw, Cecilia D Wilfred, Richard J K Taylor

Affiliations

  1. Department of Chemistry, University of York, Heslington, York, UK YO10 5DD.

PMID: 14985820 DOI: 10.1039/b315689c

Abstract

alpha-hydroxy ketones undergo manganese dioxide-mediated oxidation followed by in situ trapping with aromatic or aliphatic 1,2-diamines to give quinoxalines or dihydropyrazines, respectively, in a one-pot procedure which avoids the need to isolate the highly reactive dicarbonyl intermediates. The scope and limitations of these procedures are outlined and modifications to this procedure are discussed in which reduction is carried out in the same reaction vessel, generating piperazines, or oxidation, leading to pyrazines.

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