Visible-light induced decarboxylative alkylation of quinoxalin-2(1H)-ones at the C3-position

Abstract

3-Alkylquinoxalin-2(1H)-ones are synthesized via direct alkylation of quinoxalin-2(1H)-ones at the C3 position under visible light irradiation.

Recent Advances in Photocatalytic Functionalization of Quinoxalin‐2‐ones

“…Using this strategy, the Hu's laboratory could obtain a set of differently substituted C-3-alkylated quinoxalin-2-ones. [27] Their method efficiently tolerates the presence of various substituents at the amidic nitrogen and at the aromatic ring, when using phenyl iodide(III) diacetate (PIDA) as the methyl radical precursor. By reacting PIDA with different carboxylic acids, they could access to several phenyl iodide(III) dicarboxylates, which generated their respective C-centered radicals (Scheme 6).…”

The C3-H Bond Functionalization of Quinoxalin-2(1H)-Ones With Hypervalent Iodine(III) Reagents

“…Because of their synthetic usefulness and potential biological importance, the introduction of functional groups into the C3-position of the quinoxalin-2(1 H )-ones has already become a research hotspot, and various protocols for the direct C3-H functionalization of quinoxalin-2(1 H )-ones have been reported (Ebersol et al, 2019 ; Gu et al, 2019 ; Hong et al, 2019 ; Li et al, 2019 ; Peng et al, 2019 ; Rostoll-Berenguer et al, 2019 ; Teng et al, 2019 ; Wang et al, 2019a , 2020 ; Xie et al, 2019b ; Zhao et al, 2019 ; Zheng and Studer, 2019 ; Tian et al, 2020 ; Yuan et al, 2020 ). In particular, the C3-H functionalization of quinoxalin-2(1 H )-ones involving hypervalent iodine reagents has drawn wide attention for the aforementioned advantages of hypervalent iodine reagents, mainly including arylation (Paul et al, 2017 ; Yin and Zhang, 2017 ), trifluoromethylation (Wang et al, 2018 ; Xue et al, 2019a ), alkylation (Wang et al, 2019b ; Xie et al, 2019a ; Xue et al, 2019b ; Shen et al, 2020 ), and alkoxylation (Xu et al, 2019 ; Yang et al, 2019 ) of quinoxalin-2(1 H )-ones, which provide convenient and environmentally friendly means for the synthesis of 3-substituted quinoxalinone derivatives. In this mini review, we will focus on the progress being made in the direct C3-H functionalization of quinoxalin-2(1 H )-ones involving the hypervalent iodine reagents and discuss their mechanisms, in order to inspire more applications of hypervalent iodine reagents in related reactions.…”

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

“…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 ).…”