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. 2022 Nov 29:10:1087834.
doi: 10.3389/fchem.2022.1087834. eCollection 2022.

Visible light-promoted transition metal-free direct C3-carbamoylation of 2 H-Indazoles

Chunhua Ma  1 , Linchun Shang  1 , Hanying Zhao  1 , Xing He  1 , Qiyan Lv  2   3 , Dandan Zhang  1 , Yuqin Jiang  1
Affiliations

Visible light-promoted transition metal-free direct C3-carbamoylation of 2 H-Indazoles

Chunhua Ma et al. Front Chem. .

Abstract

We reported a general transition metal-free transformation to access C3-carbamoylated 2H-indazoles via visible light-induced oxidative decarboxylation coupling, in the presence of oxamic acids as the coupling sources, 4CzIPN as the photocatalyst, and Cs2CO3 as the base. The great application potential of this mild condition is highlighted by the late-stage modification of drugs, N-terminal modification of peptides, and the good antitumor activity of the novel desired product.

Keywords: 2H-indazole; antitumor; carbamoylation; green oxidant; photocatalysis.

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Conflict of interest statement

The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest. The handling editor declared a past co-authorship with the author QL.

Figures

FIGURE 1
FIGURE 1
The drugs and bioactive molecules with 2H-indazoles.
Scheme 1
Scheme 1
Synthetic approaches to C3-carbamoylation of 2H-indazoles.
Scheme 2
Scheme 2
The scope of 2-aryl-2H-indazoles.
Scheme 3
Scheme 3
The scope of oxamic acids.
Scheme 4
Scheme 4
The modification of drugs, natural products, and peptides.
Scheme 5
Scheme 5
The radical scavenge experiment.
Scheme 6
Scheme 6
The Stern–Volmer luminescence-quenching experiments and CV experiment.
Scheme 7
Scheme 7
The plausible reaction mechanism.
Scheme 8
Scheme 8
The antitumor activity of 4d against Ramos cell.
See this image and copyright information in PMC

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