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

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.

SUBMITTER: Hauser JR

PROVIDER: S-EPMC5082452 | biostudies-literature | 2016

REPOSITORIES: biostudies-literature

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

Hauser Jacob R JR Beard Hester A HA Bayana Mary E ME Jolley Katherine E KE Warriner Stuart L SL Bon Robin S RS

Beilstein journal of organic chemistry 20160913

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. ...[more]

PMID: 27829906

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