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Synthesis 2024; 56(23): 3680-3686
DOI: 10.1055/a-2417-9450
DOI: 10.1055/a-2417-9450
paper
Efficient and Direct Route to 5-Iodo-4H-Quinoxalines via Copper-Catalyzed Double C–N Arylations of 1,2,3-Triiodoarenes: Potential Application towards 5-Substituted 4H-Quinoxalines
The Deanship of Research at the Jordan University of Science and Technology (JUST) has provided funding for this project (Grant No. 100/2018 for R.M.A.).
Abstract
A simple, direct, and regioselective protocol to substituted 5-iodo-4H-quinoxalines through double C–N arylations of 1,2,3-triiodobenzenes and 1,2-diamines is reported. Remarkably, the N-arylation couplings proceed unimolecularly at the vicinal positions, the most active and less hindered positions. This process tolerates a wide range of aromatic substrates. The reactions of electron-deficient 1,2,3-triiodoarene systems and DMEDA under the optimized conditions provided the highest isolated yields. The chemical transformation of the target compound, which serves as a valuable precursor in synthesis, was successfully demonstrated in the Suzuki–Miyaura reaction, giving the desired coupling derivatives with excellent isolated yields. This article describes a method for the first and unprecedented synthesis of 5-iodo-4H-quinoxalines that is regioselective, scalable, and provides useful derivatives for other chemical reactions
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2417-9450.
- Supporting Information
- CIF File
Publication History
Received: 22 June 2024
Accepted after revision: 18 September 2024
Accepted Manuscript online:
18 September 2024
Article published online:
15 October 2024
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