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

Research output: Contribution to journalArticlepeer-review

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%).

Original languageEnglish
Pages (from-to)3587-3592
Number of pages6
JournalSynthesis
Volume56
Issue number23
Early online date14 Oct 2024
DOIs
Publication statusPublished - Dec 2024

Keywords

  • 2,3-diamino-5,6-dichloropyrazine
  • chlorination
  • heterocyclic building block
  • pyrazine
  • synthesis

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