Mild dealkylative N-nitrosation of N, N-dialkylaniline derivatives for convenient preparation of photo-triggered and photo-calibrated NO donors. Issue 22 (21st September 2018)

• Record Type: Journal Article
• Authors: Qiu, Shaobing; Guo, Chunlei; Wang, Mingkang; Sun, Zhenglong; Li, Hui; Qian, Xuhong; Yang, Youjun
• Is Part Of: Organic chemistry frontiers. Volume 5:Issue 22(2018)
• Page Start: 3206
• Page End: 3209
• Publication Date: 2018-09-21
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo00818c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : Direct N -nitrosation of N, N -dialkylanilines under mild, non-acidic and non-oxidative conditions. 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.