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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (12), p. 2019-2025, 2016

DOI: 10.3762/bjoc.12.189

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Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

Journal article published in 2016 by Jacob R. Hauser, Hauser Jr, Hester A. Beard, Beard Ha, Mary E. Bayana, Bayana Me, Katherine E. Jolley, Stuart L. Warriner ORCID, Jolley Ke, Warriner Sl, Robin S. Bon ORCID, Bon Rs
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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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.