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

Valentin A. Rassadin*, Vadim P. Boyarskiy and Vadim Yu. Kukushkin*

*Institute of Chemistry, Saint Petersburg State University, Universitetskii Pr. 26, Stary Petergof, 198504 Saint Petersburg, Russia, Email: v.rassadinspbu.ru, kukushkinvk2100.spb.edu

V. A. Rassadin, V. P. Boyarskiy, V. Yu. Kukushkin, Org. Lett., 2015, 17, 3502-3505.

DOI: 10.1021/acs.orglett.5b01592

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Abstract

A facile gold-catalyzed heterocyclization provides 2-amino-1,3-oxazoles functionalized at the nitrogen atom as well as at the fifth position of the heterocyclic ring in good to moderate yields. The reaction is based on intermolecular trapping of intermediate α-oxo gold carbenes with various cyanamides.

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Oxygen Atom Transfer as Key To Reverse Regioselectivity in the Gold(I)-Catalyzed Generation of Aminooxazoles from Ynamides

D. P. Zimin, D. V. Dar'in, Y. Yu. Kukushkin, A. Y. Dubovtsev, J. Org. Chem., 2021, 86, 1748-1757.

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Key Words

oxazoles, pyridine N-oxide derivatives, multicomponent reactions

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ID: J54-Y2015