4.8 Article

Facile Gold-Catalyzed Heterocyclization of Terminal Alkynes and Cyanamides Leading to Substituted 2-Amino-1,3-Oxazoles

Journal

ORGANIC LETTERS
Volume 17, Issue 14, Pages 3502-3505

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.5b01592

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Funding

  1. Saint Petersburg State University [12.38.225.2014, 12.50.1190.2014]
  2. Scientific Council of the President of the Russian Federation [MK-3228.2015.3]

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Facile gold-catalyzed heterocyclization based upon intermolecular trapping of the generated alpha-oxo gold carbenes with various cyanamides (RRNCN)-R-2-N-3 (R-2/R-3 = Alk/Alk, -(CH2)(2)O(CH2)(2)-, Ar/Ar, Ar/H) has been developed. In most cases, 2-amino-1,3-oxazoles fiinctionalized at the nitrogen atom as well as at the fifth position of the heterocyclic ring (12 examples) were isolated hi good to moderate yields.

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