TY - JOUR
T1 - An improved synthesis of 2,3-diamino-5,6-dichloropyrazine: A useful heterocyclic scaffold
AU - Rigby, Jake M.
AU - Chantry, Andrew
AU - Hemmings, Andrew M.
AU - Richards, Christopher J.
AU - Stephenson, G. Richard
AU - Storr, Thomas E.
N1 - 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.
PY - 2024/12
Y1 - 2024/12
N2 - 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%).
AB - 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%).
KW - 2,3-diamino-5,6-dichloropyrazine
KW - chlorination
KW - heterocyclic building block
KW - pyrazine
KW - synthesis
UR - http://www.scopus.com/inward/record.url?scp=85207135521&partnerID=8YFLogxK
U2 - 10.1055/s-0043-1775410
DO - 10.1055/s-0043-1775410
M3 - Article
AN - SCOPUS:85207135521
SN - 0039-7881
VL - 56
SP - 3587
EP - 3592
JO - Synthesis
JF - Synthesis
IS - 23
ER -