Hauser, JR, Beard, HA, Bayana, ME et al. (3 more authors) (2016) Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole. Beilstein Journal of Organic Chemistry, 12. pp. 2019-2025. ISSN 1860-5397
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.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Editors: |
|
Copyright, Publisher and Additional Information: | © 2016 Hauser et al.; licensee Beilstein-Institut. This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc) |
Keywords: | ACBT; cyanation; 2-cyanobenzothiazoles; DABCO; luciferins; organocatalysis |
Dates: |
|
Institution: | The University of Leeds |
Academic Units: | The University of Leeds > Faculty of Medicine and Health (Leeds) > School of Medicine (Leeds) > Leeds Institute of Genetics, Health and Therapeutics (LIGHT) > Academic Unit of Cardiovascular Medicine (Leeds) |
Funding Information: | Funder Grant number EPSRC EP/J010731/1 British Heart Foundation NH/12/1/29382 Wellcome Trust 109294/Z/15/Z |
Depositing User: | Symplectic Publications |
Date Deposited: | 22 Sep 2016 11:53 |
Last Modified: | 05 Oct 2017 16:23 |
Published Version: | http://dx.doi.org/10.3762/bjoc.12.189 |
Status: | Published |
Publisher: | Beilstein-Institut |
Identification Number: | 10.3762/bjoc.12.189 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:105017 |