New Class of Oxazine Derivatives

  • Author: ChemViews
  • Published Date: 14 April 2011
  • Source / Publisher: Chemistry - A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
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1,3-Oxazines are a well-known structural motif for biologically active substances. They exhibit antifungal, antibiotic, antiviral, and antitumor properties and are also used as acetylcholinesterase (AChE) inhibitors; potential targets for Alzheimer’s drugs.

Stephen Hashmi and co-workers, Ruprecht-Karls-Universität Heidelberg, Germany, have reported the synthesis of a new class of oxazine derivatives. The synthesis used propargylcarboxamide, a protected amine, and a source of chloride along with a copper catalyst to form a range of 5-halo-4H-1,3-oxazine-6-amines. This assembly of three simple components into an oxazine was tolerant of a wide range of functional groups. It was demonstrated that the products could be further functionalized by palladium cross-coupling reactions. This provides a simple route to new aminooxazine derivatives of pharmaceutical interest.

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Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH