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Issue 9, 2019
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Synthesis of α-aminoketones from N-sulfonyl-1,2,3-triazoles via N-sulfinyl imines generated by intramolecular oxygen transfer

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Abstract

A general procedure for intramolecular oxygen transfer from sulfonyl to a carbenoid carbon was established, extending the reaction mode of the corresponding common N-sulfonyl-1,2,3-triazoles. Indoles, and some other arenes, were employed as nucleophiles to react with the resulting key N-sulfinyl imine intermediate, and valuable α-aminoketones could be synthesized conveniently. The synthetic utility of the products was further exhibited by convenient synthesis of gem-diaryl ketones and densely substituted pyrrole. A tentative reaction mechanism was proposed according to control experiments.

Graphical abstract: Synthesis of α-aminoketones from N-sulfonyl-1,2,3-triazoles via N-sulfinyl imines generated by intramolecular oxygen transfer

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Publication details

The article was received on 25 Jan 2019, accepted on 04 Mar 2019 and first published on 05 Mar 2019


Article type: Research Article
DOI: 10.1039/C9QO00126C
Citation: Org. Chem. Front., 2019,6, 1391-1396

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    Synthesis of α-aminoketones from N-sulfonyl-1,2,3-triazoles via N-sulfinyl imines generated by intramolecular oxygen transfer

    Z. Xu, L. Shan, W. Zhang, M. Cen and C. Li, Org. Chem. Front., 2019, 6, 1391
    DOI: 10.1039/C9QO00126C

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