Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole.
2-Cyanobenzothiazoles (CBTs) are useful building blocks for: 1) luciferin derivatives for bioluminescent imaging; and 2) handles for bioorthogonal ligations. A particularly versatile CBT is 6-amino-2-cyanobenzothiazole (ACBT), which has an amine handle for straight-forward derivatisation. Here we present an economical and scalable synthesis of ACBT based on a cyanation catalysed by 1,4-diazabicyclo[2.2.2]octane (DABCO), and discuss its advantages for scale-up over previously reported routes.
School of Chemistry, University of Leeds; Astbury Centre for Structural Molecular Biology.
Jacob R
JR
Hauser
School of Chemistry, University of Leeds; Astbury Centre for Structural Molecular Biology.
Hester A
HA
Beard
School of Chemistry, University of Leeds; Institute of Process Research and Development.
Mary E
ME
Bayana
School of Chemistry, University of Leeds; Institute of Process Research and Development.
Katherine E
KE
Jolley
School of Chemistry, University of Leeds; Astbury Centre for Structural Molecular Biology.
Stuart L
SL
Warriner
Astbury Centre for Structural Molecular Biology; Leeds Institute of Cardiovascular and Metabolic Medicine, LIGHT Laboratories, University of Leeds, Leeds LS2 9JT, UK.
Robin S
RS
Bon
2-cyanobenzothiazoles; ACBT; DABCO; cyanation; luciferins; organocatalysis