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Synthesis 2024; 56(23): 3587-3592
DOI: 10.1055/s-0043-1775410
DOI: 10.1055/s-0043-1775410
psp
An Improved Synthesis of 2,3-Diamino-5,6-dichloropyrazine: A Useful Heterocyclic Scaffold
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.
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(1H)-one is rapid, enabling access to 2,3-diamino-5,6-dichloropyrazine in an improved overall yield (41%).
Key words
pyrazine - heterocyclic building block - synthesis - chlorination - 2,3-diamino-5,6-dichloropyrazineSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1775410.
- Supporting Information
Publication History
Received: 21 August 2024
Accepted: 18 September 2024
Article published online:
14 October 2024
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