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

Jacob R. Hauser, Hester A. Beard, Mary E. Bayana, Katherine E. Jolley, Stuart L. Warriner and Robin S. Bon
Beilstein J. Org. Chem. 2016, 12, 2019–2025. https://doi.org/10.3762/bjoc.12.189

Supporting Information

Supporting Information File 1: Copies of 1H and 13C NMR spectra, details of calorimetry experiments and comparison of routes to ACBT 8.
Format: PDF Size: 1.6 MB Download

Cite the Following Article

Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole
Jacob R. Hauser, Hester A. Beard, Mary E. Bayana, Katherine E. Jolley, Stuart L. Warriner and Robin S. Bon
Beilstein J. Org. Chem. 2016, 12, 2019–2025. https://doi.org/10.3762/bjoc.12.189

How to Cite

Hauser, J. R.; Beard, H. A.; Bayana, M. E.; Jolley, K. E.; Warriner, S. L.; Bon, R. S. Beilstein J. Org. Chem. 2016, 12, 2019–2025. doi:10.3762/bjoc.12.189

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 118.7 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Sondag, D.; Heming, J. J. A.; Löwik, D. W. P. M.; Krivosheeva, E.; Lejeune, D.; van Geffen, M.; Van't Veer, C.; van Heerde, W. L.; Beens, M. C. J.; Kuijpers, B. H. M.; Boltje, T. J.; Rutjes, F. P. J. T. Solid-Phase Synthesis of Caged Luminescent Peptides via Side Chain Anchoring. Bioconjugate chemistry 2023, 34, 2234–2242. doi:10.1021/acs.bioconjchem.3c00381
  • Chang, C.-H.; Fontaine, D. M.; Gómez, S.; Branchini, B. R.; Anderson, J. C. Synthesis and Bioluminescence of 'V'-Shaped Firefly Luciferin Analogues Based on A Novel Benzobisthiazole Core. Chemistry (Weinheim an der Bergstrasse, Germany) 2023, 29, e202302204. doi:10.1002/chem.202302204
  • Broudic, N.; Pacheco-Benichou, A.; Fruit, C.; Besson, T. Synthesis of 2-Cyanobenzothiazoles via Pd-Catalyzed/Cu-Assisted C-H Functionalization/Intramolecular C-S Bond Formation from N-Arylcyanothioformamides. Molecules (Basel, Switzerland) 2022, 27, 8426. doi:10.3390/molecules27238426
  • Hampton, J. T.; Lalonde, T. J.; Tharp, J. M.; Kurra, Y.; Alugubelli, Y. R.; Roundy, C. M.; Hamer, G. L.; Xu, S.; Liu, W. R. Novel Regioselective Approach to Cyclize Phage-Displayed Peptides in Combination with Epitope-Directed Selection to Identify a Potent Neutralizing Macrocyclic Peptide for SARS-CoV-2. ACS chemical biology 2022, 17, 2911–2922. doi:10.1021/acschembio.2c00565
  • Deng, C.; Huang, J.; Qi, Y.; Chen, D.; Huang, W. Distribution patterns of rubber tire-related chemicals with particle size in road and indoor parking lot dust. The Science of the total environment 2022, 844, 157144. doi:10.1016/j.scitotenv.2022.157144
  • Sondag, D.; Merx, J.; Rossing, E.; Boltje, T. J.; Löwik, D. W. P. M.; Nelissen, F. H. T.; van Geffen, M.; van 't Veer, C.; van Heerde, W. L.; Rutjes, F. P. J. T. Luminescent Assay for the Screening of SARS-CoV-2 MPro Inhibitors. Chembiochem : a European journal of chemical biology 2022, 23, e202200190. doi:10.1002/cbic.202200190
  • Hu, S.; Chen, X.; Qin, X.; Dong, G.; Lin, Y.; Gai, W.; Zhao, H.; Ke, B.; Li, M. A bioluminescent probe for in vivo imaging of pyroglutamate aminopeptidase in a mouse model of inflammation. Bioorganic & medicinal chemistry letters 2021, 43, 128049. doi:10.1016/j.bmcl.2021.128049
  • Pala, L.; Sirec, T.; Spitz, U. Modified Enzyme Substrates for the Detection of Bacteria: A Review. Molecules (Basel, Switzerland) 2020, 25, 3690. doi:10.3390/molecules25163690
  • Bugaenko, D. I.; Karchava, A. V.; Yurovskaya, M. A. The versatility of DABCO: synthetic applications of its basic, nucleophilic, and catalytic properties. Chemistry of Heterocyclic Compounds 2020, 56, 265–278. doi:10.1007/s10593-020-02655-y
  • Kovács, A. K.; Hegyes, P.; Szebeni, G. J.; Nagy, L.; Puskás, L. G.; Tóth, G. Synthesis of N-peptide-6-amino-D-luciferin Conjugates. Frontiers in chemistry 2018, 6, 120. doi:10.3389/fchem.2018.00120
  • Vacher, M.; Galván, I. F.; Ding, B.-W.; Schramm, S.; Berraud-Pache, R.; Naumov, P.; Ferré, N.; Liu, Y.-J.; Navizet, I.; Roca-Sanjuán, D.; Baader, W. J.; Lindh, R. Chemi- and Bioluminescence of Cyclic Peroxides. Chemical reviews 2018, 118, 6927–6974. doi:10.1021/acs.chemrev.7b00649
  • Sharma, D.; Adams, S. T.; Liebmann, K. L.; Miller, S. C. Rapid Access to a Broad Range of 6'-Substituted Firefly Luciferin Analogues Reveals Surprising Emitters and Inhibitors. Organic letters 2017, 19, 5836–5839. doi:10.1021/acs.orglett.7b02806
  • Rathbun, C. M.; Prescher, J. A. Bioluminescent Probes for Imaging Biology beyond the Culture Dish. Biochemistry 2017, 56, 5178–5184. doi:10.1021/acs.biochem.7b00435
  • Hauser, J. R.; Beard, H. A.; Bayana, M. E.; Jolley, K. E.; Warriner, S. L.; Bon, R. S. Economical and Scalable Synthesis of 6‐Amino‐2‐cyanobenzothiazole. ChemInform 2016, 47. doi:10.1002/chin.201650112
Other Beilstein-Institut Open Science Activities