An improved synthesis of 2,3-diamino-5,6-dichloropyrazine: A useful heterocyclic scaffold

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Rigby, 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
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Depositing User: LivePure Connector
Date Deposited: 30 Jan 2025 17:30
Last Modified: 05 Feb 2025 13:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/98335
DOI: 10.1055/s-0043-1775410

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