Organic Letters
Organic Letters
5 years ago

Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles

Mechanistic Pathways in Amide Activation: Flexible Synthesis of Oxazoles and Imidazoles
Saad Shaaban, Daniel Kaiser, Leticia González, Nuno Maulide, Giovanni Di Mauro, Boris Maryasin
The preparation of substituted aminooxazoles and aminoimidazoles from α-arylamides and α-aminoamides through triflic anhydride-mediated amide activation is reported. These reactions proceed via the intermediacy of nitrilium adducts and feature N-oxide-promoted umpolung of the α-position of amides as well as a mechanistically intriguing sequence that results in sulfonyl migration from nitrogen to carbon. Quantum-chemical mechanistic analysis sheds light on the intricacies of the process.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01678

DOI: 10.1021/acs.orglett.7b01678

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