Mallick, Rajendra K. ; Prabagar, B. ; Sahoo, Akhila K. (2017) Regioselective Synthesis of 2,4,5-Trisubstituted Oxazoles and Ketene Aminals via Hydroamidation and Iodo-Imidation of Ynamides Journal of Organic Chemistry, 82 (19). pp. 10583-10594. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/acs.joc.7b02124
Related URL: http://dx.doi.org/10.1021/acs.joc.7b02124
Abstract
A novel and straightforward protocol is demonstrated for the synthesis of highly substituted oxazoles from readily accessible ynamides in the presence of ytterbium(III) trifluoromethanesulfonate [Yb(OTf)3], N-iodosuccinimide (NIS), and acetonitrile. Multiple oxazole skeletons in the aryl periphery are constructed in a single operation for the first time. The hydroamidation and iodo-imidation of ynamides to trisubstituted and tetrasubstituted ketene aminals is exemplified. An isotope labeling experiment is used to identify the oxygen source in this transformation. The reactions are scalable to the gram scale, testifying the robustness of the transformations.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 121871 |
| Deposited On: | 22 Jul 2021 18:38 |
| Last Modified: | 22 Jul 2021 18:38 |
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