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Regioselective Synthesis of 2,4,5-Trisubstituted Oxazoles and Ketene Aminals via Hydroamidation and Iodo-Imidation of Ynamides

Rajendra K. Mallick, B. Prabagar and Akhila K. Sahoo*

*School of Chemistry, University of Hyderabad, Hyderabad 500046, India, Email: aksscuohyd.ac.in

R. K. Mallick, B. Prabagar, A. K. Sahoo, J. Org. Chem., 2017, 82, 10583-10594.

DOI: 10.1021/acs.joc.7b02124 (free Supporting Information)



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Abstract

Highly substituted oxazoles can be synthesized from readily accessible ynamides in the presence of ytterbium(III) trifluoromethanesulfonate, N-iodosuccinimide, and acetonitrile. Hydroamidation and iodo-imidation of ynamides to ketene aminals are also demonstrated. The reactions are scalable to the gram scale, testifying the robustness of the transformations.

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Key Words

oxazoles, NIS


ID: J42-Y2017