Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole.
- Resource Type
- Academic Journal
- Authors
- Hauser JR; School of Chemistry, University of Leeds; Astbury Centre for Structural Molecular Biology.; Beard HA; School of Chemistry, University of Leeds; Astbury Centre for Structural Molecular Biology.; Bayana ME; School of Chemistry, University of Leeds; Institute of Process Research and Development.; Jolley KE; School of Chemistry, University of Leeds; Institute of Process Research and Development.; Warriner SL; School of Chemistry, University of Leeds; Astbury Centre for Structural Molecular Biology.; Bon RS; Astbury Centre for Structural Molecular Biology; Leeds Institute of Cardiovascular and Metabolic Medicine, LIGHT Laboratories, University of Leeds, Leeds LS2 9JT, UK.
- Source
- Publisher: Beilstein-Institut Country of Publication: Germany NLM ID: 101250746 Publication Model: eCollection Cited Medium: Print ISSN: 1860-5397 (Print) Linking ISSN: 18605397 NLM ISO Abbreviation: Beilstein J Org Chem Subsets: PubMed not MEDLINE
- Subject
- Language
- English
- ISSN
- 1860-5397
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.