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ToolsRigby, Jake M., Chantry, Andrew, Hemmings, Andrew M., Richards, Christopher J., Stephenson, G. Richard and Storr, Thomas E. (2024) An improved synthesis of 2,3-diamino-5,6-dichloropyrazine: A useful heterocyclic scaffold. Synthesis, 56 (23). pp. 3587-3592. ISSN 0039-7881
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Abstract
2,3-Diamino-5,6-dichloropyrazine represents a valuable but underexplored heterocyclic building block. Due to the use of harsh conditions and lack of selectivity surrounding the known literature synthesis, we developed a more accessible and selective three-step route from 2-aminopyrazine. Challenging conditions are avoided by using a high-yielding dichlorination with N -chlorosuccinimide (NCS), which is followed by a regioselective amination. The installation of the last chlorine atom using 1-chloro-1,2-benziodoxol-3(1 H)-one is rapid, enabling access to 2,3-diamino-5,6-dichloropyrazine in an improved overall yield (41%).
| Item Type: | Article |
|---|---|
| Additional Information: | Funding information: This work was supported by funding to G.R.S from BigC Cancer Charity (Research Grant 16-17R) supporting a PhD studentship for J.M.R. |
| Uncontrolled Keywords: | 2,3-diamino-5,6-dichloropyrazine,chlorination,heterocyclic building block,pyrazine,synthesis,catalysis,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1500/1503 |
| Faculty \ School: | Faculty of Science > School of Chemistry (former - to 2024) Faculty of Science > School of Biological Sciences Faculty of Science > School of Chemistry, Pharmacy and Pharmacology |
| UEA Research Groups: | Faculty of Science > Research Groups > Plant Sciences Faculty of Science > Research Groups > Molecular Microbiology Faculty of Science > Research Groups > Chemistry of Life Processes Faculty of Science > Research Centres > Centre for Molecular and Structural Biochemistry |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 30 Jan 2025 17:30 |
| Last Modified: | 31 Oct 2025 01:09 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/98335 |
| DOI: | 10.1055/s-0043-1775410 |
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