Gold Catalysis: Mild Conditions for the Synthesis of Oxazoles from N -Propargylcarboxamides and Mechanistic Aspects

  • Hashmi A
  • Weyrauch J
  • Frey W
 et al. 
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Abstract

2,5-Disubstituted oxazoles are synthesized from the corresponding propargylcarboxamides under mild reaction conditions via homogeneous catalysis by AuCl(3). While monitoring the conversion via (1)H NMR spectroscopy, an intermediate 5-methylene-4,5-dihydrooxazole can be observed and accumulated up to 95%, being the first direct and catalytic preparative access to such alkylidene oxazolines. The intermediate was fully characterized and can be trapped at -25 degrees C for several weeks. Deuteration experiments show a stereospecific mode of the two first steps of the reaction.

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Authors

  • a Stephen K Hashmi

  • Jan P Weyrauch

  • Wolfgang Frey

  • Jan W Bats

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