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Economical and Scalable Synthesis of 6-amino-2-cyanobenzothiazole


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Abstract

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.

Reference:

Hauser, J. R., Beard, H. A., Bayana, M. E., Jolley, K. E., Warriner, S. L., & Bon, R. S. (2016). Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole. Beilstein Journal of Organic Chemistry, 12, 2019-2025. doi:10.3762/bjoc.12.189


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