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Mild dealkylative N-nitrosation of N,N-dialkylaniline derivatives for convenient preparation of photo-triggered and photo-calibrated NO donors

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Abstract

N-Nitroso push–pull dyes are unique NO donors, whose NO release is triggered by light and accompanied by a concomitant fluorescence turn-on. Their synthesis involves nitrosation of the corresponding secondary amines, which, however, are not readily available. In this manuscript, we developed a mild, convenient and high-yielding preparation of N-nitroso aryl amines via dealkylative N-nitrosation of tertiary amines. This method is readily employed for the preparation of N-nitrosated rhodamine and coumarin dyes, whose potential as novel NO donors were showcased in cultured cell lines.

Graphical abstract: Mild dealkylative N-nitrosation of N,N-dialkylaniline derivatives for convenient preparation of photo-triggered and photo-calibrated NO donors

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Publication details

The article was received on 03 Aug 2018, accepted on 12 Sep 2018 and first published on 14 Sep 2018


Article type: Research Article
DOI: 10.1039/C8QO00818C
Citation: Org. Chem. Front., 2018, Advance Article
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    Mild dealkylative N-nitrosation of N,N-dialkylaniline derivatives for convenient preparation of photo-triggered and photo-calibrated NO donors

    S. Qiu, C. Guo, M. Wang, Z. Sun, H. Li, X. Qian and Y. Yang, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C8QO00818C

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