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

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.