Beilstein J. Org. Chem.2018,14, 2411–2417, doi:10.3762/bjoc.14.218
related to hinckdentine A received increasing attention as a source of new and useful pharmaceuticals. One well-established approach is based on the elaboration of a preformed indole ring, for example through cyclocondensation of 2-(o-aminophenyl)indoles with 2-cyanobenzothiazoles [14], aldehydes [9] and
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Graphical Abstract
Scheme 1:
Synthesis of 6-trifluoromethyl-12-aryl(vinyl)indolo[1,2-c]quinazolines 4.
Beilstein J. Org. Chem.2016,12, 2019–2025, doi:10.3762/bjoc.12.189
Laboratories, University of Leeds, Leeds LS2 9JT, UK 10.3762/bjoc.12.189 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
-cyanobenzothiazoles; DABCO; luciferins; organocatalysis; Introduction
Functionalised 2-cyanobenzothiazoles (CBTs, 1) are key building blocks for the synthesis of luciferins 3 [1][2][3], substrates of natural and engineered firefly luciferases that are widely used for bioluminescence imaging (BLI) [4][5]. The typical
), 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.
Keywords: ACBT; cyanation; 2
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Graphical Abstract
Scheme 1:
Functionalised CBTs 1 can be used for the synthesis of luciferins 3 and for bioorthogonal ligations...