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

Dmitry P. Zimin, Dmitry V. Dar’in, Vadim Yu. Kukushkin* and Alexey Yu. Dubovtsev*

*Saint Petersburg State University, Universitetskaya Nab. 7/9, 199034 Saint Petersburg, Russian Federation, Email: v.kukushkinspbu.ru, a.dubovtsevspbu.ru

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

DOI: 10.1021/acs.joc.0c02584 (free Supporting Information)


Abstract

A gold(I)-catalyzed oxidative annulation involving ynamides, nitriles, and 2,3-dichloropyridine N-oxide provides 5-amino-1,3-oxazoles. In addition, the use cyanamides instead of nitriles provides difficult-to-obtain 2,5-diaminooxazoles. The process is feasible for wide ranges of ynamides or nitriles, and it can be conducted in gram scale.

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

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


Key Words

oxazoles, pyridine-N-oxides


ID: J42-Y2021