Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides

Irwan Iskandar Roslan, Kian-Hong Ng, Gaik-Khuan Chuah and Stephan Jaenicke
Beilstein J. Org. Chem. 2017, 13, 2739–2750. https://doi.org/10.3762/bjoc.13.270

Supporting Information

Supporting Information File 1: Experimental procedure, analytical data and NMR spectra.
Format: PDF Size: 4.6 MB Download

Cite the Following Article

Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides
Irwan Iskandar Roslan, Kian-Hong Ng, Gaik-Khuan Chuah and Stephan Jaenicke
Beilstein J. Org. Chem. 2017, 13, 2739–2750. https://doi.org/10.3762/bjoc.13.270

How to Cite

Roslan, I. I.; Ng, K.-H.; Chuah, G.-K.; Jaenicke, S. Beilstein J. Org. Chem. 2017, 13, 2739–2750. doi:10.3762/bjoc.13.270

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: 156.4 KB Download

Citations to This Article

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

Scholarly Works

  • Aljaar, N.; Aboalrub, H. F.; Shtaiwi, M.; Sarhan, A. H. A.; Younes, E. A.; Al‐Noaimi, M.; Shtaiwi, A.; Tahtamouni, L. H.; Abu‐Safieh, K. A.; AlObaid, A. A.; Malakar, C. C. Cu‐Catalyzed Synthesis of 4H‐benzo[4,5]thiazolo[3,2‐a]pyrimidin‐4‐ones: Molecular Docking Studies and Anti‐Proliferative Activities Against HepG2 Hepatocellular Carcinoma Cells. Asian Journal of Organic Chemistry 2024, 13. doi:10.1002/ajoc.202400065
  • Chekh, A. S.; Korochentsev, V. V.; Vovna, V. I.; Shurygin, A. V. Electronic structure and photoelectron spectra of fluorinated ZnII thioacetylacetonate complexes. Russian Chemical Bulletin 2022, 71, 1209–1223. doi:10.1007/s11172-022-3522-2
  • Ferry, A.; Guinchard, X. Comprehensive Heterocyclic Chemistry IV - Bicyclic 5-5 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: Two Extra Heteroatoms 1:1. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 95–144. doi:10.1016/b978-0-12-409547-2.14934-0
  • Budnikov, A. S.; Krylov, I. B.; Lastovko, A. V.; Paveliev, S. A.; Romanenko, A. R.; Nikishin, G. I.; Terent'ev, A. O. Stable and reactive diacetyliminoxyl radical in oxidative C-O coupling with β-dicarbonyl compounds and their complexes. Organic & biomolecular chemistry 2021, 19, 7581–7586. doi:10.1039/d1ob01269j
  • Vovna, V. I.; Chekh, A. S.; Korochentsev, V. V.; Tikhonov, S. A.; Samoilov, I. S. Photoelectron spectra and electronic structure of Zn(II)bis-β-diketonates with aromatic substituents by the PES, DFT, and OVGF methods. Journal of Molecular Structure 2021, 1223, 128815. doi:10.1016/j.molstruc.2020.128815
  • Roslan, I. I.; Zhang, H.; Ng, K.-H.; Jaenicke, S.; Chuah, G.-K. A Visible Light and Iron‐mediated Carbocationic Route to Polysubstituted 1‐Halonaphthalenes by Benzannulation using Allylbenzenes and Polyhalomethanes. Advanced Synthesis & Catalysis 2020, 363, 1007–1013. doi:10.1002/adsc.202001249
  • Ciccolini, C.; Mari, G.; Gatti, F. G.; Gatti, G.; Giorgi, G.; Mantellini, F.; Favi, G. Synthesis of Polycyclic Fused Indoline Scaffolds through a Substrate-Guided Reactivity Switch. The Journal of organic chemistry 2020, 85, 11409–11425. doi:10.1021/acs.joc.0c01489
  • Zhao, J.-W.; Xiao, Q.; Chen, J.; Xu, J.-X. Metal‐Free Synthesis of Imidazo[2,1‐b]thiazoles from Thioimidazoles and Ketones Mediated by Selectfluor. European Journal of Organic Chemistry 2020, 2020, 5201–5206. doi:10.1002/ejoc.202000815
  • Mohaddesi, M.; Pesyan, N. N. Fe3O4@SiO2 nanoparticle-immobilized Cu(II)-benzoylthiourea complex as a magnetically reusable catalyst for the synthesis of benzo[d]imidazo[2,1-b]thiazole-1-ium hydroxide derivatives in water. Journal of the Iranian Chemical Society 2020, 17, 2105–2117. doi:10.1007/s13738-020-01915-0
  • Mukku, N.; Maiti, B. On water catalyst-free synthesis of benzo[ d ]imidazo[2,1- b ] thiazoles and novel N -alkylated 2-aminobenzo[ d ]oxazoles under microwave irradiation. RSC advances 2020, 10, 770–778. doi:10.1039/c9ra08929b
  • Roslan, I. I.; Ng, K.-H.; Jaenicke, S.; Chuah, G.-K. Photocatalytic regeneration of brominating agent in the visible light-mediated synthesis of imidazo[1,2-a]pyridines. Catalysis Science & Technology 2019, 9, 1528–1534. doi:10.1039/c9cy00141g
  • Etivand, N.; Sabegh, M. A.; Khalafy, J. Synthesis of a new series of benzo[ d ]imidazo[2,1- b ]thiazole-1-ium hydroxides by a one-pot, three-component reaction in water. Monatshefte für Chemie - Chemical Monthly 2019, 150, 317–325. doi:10.1007/s00706-018-2315-7
  • Roslan, I. I.; Ng, K.-H.; Gondal, M. A.; Basheer, C.; Dastageer, M. A.; Jaenicke, S.; Chuah, G.-K. Visible Light-Mediated Coupling of Thioureas and 1,3-Dicarbonyls: Towards a Leaving Group-Free Synthesis of Aminothiazoles. Advanced Synthesis & Catalysis 2018, 360, 1584–1589. doi:10.1002/adsc.201701565
  • Kysil, A. I.; Biitseva, A. V.; Yegorova, T.; Levkov, I. V.; Voitenko, Z. Reaction of 1-aminoisoindole with methyl 4-chloro-3-oxobutanoate. French-Ukrainian Journal of Chemistry 2018, 6, 32–37. doi:10.17721/fujcv6i2p32-37
  • Roslan, I. I.; Ng, K.-H.; Chuah, G.-K.; Jaenicke, S. Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides. Beilstein journal of organic chemistry 2017, 13, 2739–2750. doi:10.3762/bjoc.13.270
Other Beilstein-Institut Open Science Activities