Photophysical properties of quinoxalin-2(1H)-ones: application in the preparation of an azide-based fluorogenic probe for the detection of hydrogen sulfide

Abstract

Fluorescent quinoxalinones with good quantum yields were obtained and used in the preparation of a probe for the detection of H2S.

Visible‐Light‐Promoted Switchable Synthesis of C‐3‐Functionalized Quinoxalin‐2(1H)‐ones

“…Moreover, while the reduced derivatives of quinoxalin‐2(1 H )‐ones at the carbonyl groups could show fluorogenic properties (Figure 1), [5] the photophysical properties of these derivatives have been relatively overlooked, [6] with only a limited number of studies focusing on their fluorogenic properties having been reported to date [2c,5] . This is somewhat surprising, as these derivatives have potential utility as fluorogenic probes for the detection of valuable bioactive substances [5] . For example, this photophysical property of the quinoxalin‐2(1 H )‐ones could be used in chemo‐sensing studies or to monitor biological reactions.…”

“…Yuan and Mao employed Cu 2 O and tert ‐butyl peroxybenzoate in the oxidative coupling of quinoxalin‐2(1 H )‐ones with alcohols to obtain the desired products [4] . Moreover, while the reduced derivatives of quinoxalin‐2(1 H )‐ones at the carbonyl groups could show fluorogenic properties (Figure 1), [5] the photophysical properties of these derivatives have been relatively overlooked, [6] with only a limited number of studies focusing on their fluorogenic properties having been reported to date [2c,5] . This is somewhat surprising, as these derivatives have potential utility as fluorogenic probes for the detection of valuable bioactive substances [5] .…”

“…We then performed a fluorescent labelling experiment to highlight the fluorescent property of the hydroxyl‐containing products 4 [15] . Hydroxyl‐containing quinoxalin‐2(1 H )‐ones 4 show noticeable fluorescent properties [2c,5] …”

“…[2c,5] This is somewhat surprising, as these derivatives have potential utility as fluorogenic probes for the detection of valuable bioactive substances. [5] For example, this photophysical property of the quinoxalin-2(1H)-ones could be used in chemo-sensing studies or to monitor biological reactions. Clearly, the value of an efficient and direct means of synthesizing hydroxyl-containing quinoxalin-2(1H)-ones is not sufficiently appreciated.…”

Iron(III)-Mediated Rapid Radical-Type Three-Component Deuteration of Quinoxalinones With Olefins and NaBD4

“…Multicomponent reactions have become a hot field in modern organic chemistry in recent years because multicomponent reaction can form multiple chemical bonds in one step in comparison with the traditional synthesis method, thus realizing the simple, efficient, and atomic economic synthesis of structural diversity compounds. Quinoxalines and their derivatives are one of the important organic compounds because they have been widely applied in organic synthesis, material chemistry, agrochemical industries, and pharmaceutical chemistry (TenBrink et al, 1994 ; Monge et al, 1995 ; Badran et al, 2003 ; Refaat et al, 2004 ; Hoogewijs et al, 2013 ; Nakane et al, 2015 ; Renault et al, 2017 ). Although a plenty of two-component reactions for the synthesis of quinoxalinones were achieved (Hong et al, 2019 ; Jin et al, 2019 ; Ke et al, 2019 ; Liu et al, 2019 ; Wang et al, 2019 , 2020 ; Wei et al, 2019 ; Xie et al, 2019 ; Xue et al, 2019 ; Yan et al, 2019 ; Zhang H. et al, 2019 ; Zhang W. et al, 2019 ; Bao et al, 2020 ).…”