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

Valentin A Rassadin; Vadim P Boyarskiy; Vadim Yu Kukushkin

doi:10.1021/acs.orglett.5b01592

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

Org Lett. 2015 Jul 17;17(14):3502-5. doi: 10.1021/acs.orglett.5b01592. Epub 2015 Jul 2.

Authors

Valentin A Rassadin¹, Vadim P Boyarskiy¹, Vadim Yu Kukushkin¹

Affiliation

¹ Institute of Chemistry, Saint Petersburg State University, Universitetskii Pr. 26, Stary Petergof, 198504 Saint Petersburg, Russia.

PMID: 26135038
DOI: 10.1021/acs.orglett.5b01592

Abstract

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