16112-21-3Relevant articles and documents
Synthesis of 2-aryl and coumarin substituted benzothiazole derivatives
Kenny, Rajesh S.,Mashelkar, Uday C.
, p. 1367 - 1369 (2006)
A facile and effective method for the synthesis of some benzothiazole derivatives is described. The method involves the action of aryl aldehyde and o-aminothiophenol in acetic acid resulting into in situ formation of the thiol substituted Schiffs base and
Mono- and binuclear palladacycles via regioselective C-H bond activation: Syntheses, mechanistic insights and catalytic activity in direct arylation of azoles
Pandey, Dilip K.,Khake, Shrikant M.,Gonnade, Rajesh G.,Punji, Benudhar
, p. 81502 - 81514 (2015)
Regioselective C-H bond palladation of the hybrid pincer-type ligands, 3-R2PO-C6H4-1-CH2NiPr2 [R2POCNiPr2-H; R = Ph (1a), R = Et2N (1b)] has been described
A simple synthesis of 2-arylbenzothiazoles and its application to palladium-catalyzed Mizoroki-Heck reaction
Kawashita, Yuka,Ueba, Chigusa,Hayashi, Masahiko
, p. 4231 - 4233 (2006)
A variety of 2-arylbenzothiazoles were prepared by the direct reaction of 2-aminobenzenethiol and aryl aldehydes by the aid of activated carbon (Shirasagi KL or Darco KB) under oxygen atmosphere. 2-Pyridylbenzothiazole, thus obtained, was proved to work as an efficient ligand in palladium-catalyzed Mizoroki-Heck reaction.
Microwave-assisted synthesis of benzothiazole derivatives using glycerol as green solvent
Zhang, Xia-Zhong,Zhou, Wen-Jun,Yang, Min,Wang, Jin-Xian,Bai, Lin
, p. 489 - 491 (2012)
A rapid method has been developed for the synthesis of benzothiazoles via the condensation of 2-aminothiophenol with aldehydes under CEM-focused microwave irradiation conditions. The reaction used glycerol as a green solvent without any catalyst, renderin
Direct C—H Bond Activation of Benzoxazole and Benzothiazole with Aryl Bromides Catalyzed by Palladium(II)-N-heterocyclic Carbene Complexes
Kalo?lu, Murat,Kalo?lur, Nazan,?zdemir, ?smail
, p. 837 - 844 (2018)
Herein, we report that a series of novel palladium(II)-NHC complexes (NHC=N-heterocyclic carbene) were synthesized. The structures of all novel complexes were characterized by 1H NMR, 13C NMR, FT-IR spectroscopy and elemental analysis techniques. These palladium(II)-NHC complexes were tested as efficient catalysts in the direct C—H bond activation of benzoxazole and benzothiazole with aryl bromides in the presence of 1 mol% catalyst loading at 150 °C for 4 h. Under the given conditions, various aryl bromides were successfully applied as the arylating reagents to achieve the 2-arylbenzoxazoles and 2-arylbenzothiazoles in acceptable to high yields.
Anchoring of Cu(II) onto surface of porous metal-organic framework through post-synthesis modification for the synthesis of benzimidazoles and benzothiazoles
Kardanpour, Reihaneh,Tangestaninejad, Shahram,Mirkhani, Valiollah,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Zadehahmadi, Farnaz
, p. 145 - 153 (2016)
Efficient synthesis of various benzimidazoles and benzothiazoles under mild conditions catalyzed by Cu(II) anchored onto UiO-66-NH2 metal organic framework is reported. In this manner, first, the aminated UiO-66 was modified with thiophene-2-ca
Synthesis, in vitro and structural aspects of benzothiazole analogs as anti-oxidants and potential neuroprotective agents
Chandana, Nuthakki Venkata,Karthikeyan, Divyapriya,Mathavan, Sivagami,Ramachandran, Srimathy,Ramaiah, M. Janaki,Vasavi, P. Jaya,Yamajala, Rajesh B. R. D.
, (2020)
Catalase, an important antioxidant enzyme, is known to have a neuroprotective role against neurodegenerative disorder. Earlier study has focussed on benzothiazole-triazole hybrid molecules that are larger in size and molecular weight and inhibit the amyloid β (Aβ)-catalase interaction thus aid in neuroprotection. Here we have synthesized the novel benzothiazole molecules with low molecular weight using One-pot methodology and assayed the neuroprotective effects of the synthesized compounds in the U87 MG cell line under H2O2 induced stressed condition and compared with other cell lines such as breast cancer (MCF-7) and macrophage (RAW-264.7) using cell viability assay. These analogs were found to enhance the neuronal cell viability and protect neuronal cells from the ROS mediated neuronal damage induced by H2O2. Furthermore, compounds 6a, 6b, 6c, 6d, and 7a modulate catalase and enhanced the catalase activity up to 90 percent during the H2O2 exposure in the U87MG cell line. These analogs (6a, 6b, 6c and 6d) have exhibited strong binding energies of -7.39, -7.52, -6.5 and -7.1 as observed by molecular modeling studies using AutoDockTool-1.5.6. Lig Plot + program using potent analogs 6b and 6c and catalase enzyme indicated the presence of hydrophobic interactions in the catalytic site of catalase enzyme. Furthermore, a simulation study was conducted between ligand and catalase protein by DESMOND software that further strengthens these ligand and enzyme interactions. In silico ADMET study was conducted by the Swiss ADME program revealed the drug-likeliness of these analogs. The present study has identified benzothiazole analogs such as 6b, 6c and 6d have potential catalase modulating activity and is comparable with that of known drug Valproic acid, thus help in neuroprotection. This study can be further taken up for the in vivo animal model study for the possible therapy.
Synthesis of 2-Arylbenzothiazoles from Nitrobenzenes, Benzylamines, and Elemental Sulfur via Redox Cyclization
Imoto, Mitsutaka,Mizuno, Takumi,Nomoto, Akihiro,Ogawa, Akiya,Takeda, Motonori,Teramoto, Masahiro
supporting information, p. 386 - 390 (2022/03/02)
A sustainable advanced synthetic method was developed based on redox cyclization for the synthesis of 2-arylbenzothiazoles in good to excellent yields from readily available nitrobenzenes, benzylamines, and elemental sulfur without the use of transition-metal catalysts. This method is remarkable: nitro group reduction, a benzylamine redox reaction, sulfuration, condensation, and cyclization, all proceed in a single step to generate a heterocycle. It is also highly atom-economical and does not require any external oxidizing or reducing agents.
Graphene oxide-catalyzed synthesis of benzothiazoles with amines and elemental sulfur via oxidative coupling strategy of amines to imines
He, Haiping,Duan, Dehao,Li, Hong,Wei, Yifei,Nie, Liang,Tang, Bo,Wang, Hanyu,Han, Xiaowei,Huang, Panpan,Peng, Xiangjun
, (2022/01/13)
The graphene oxide-catalyzed coupling and cyclization reactions of primary amines with elemental sulfur was developed to afford various optically property benzothiazoles. This coupling and cyclization strategies proceeded under the oxidant system graphene oxide/O2 and constructed carbon-heteroatom (N, S) bonds with amines and elemental sulfur. Due to benzothiazoles as common chromophores, these products exhibited intriguing fluorescence properties, including outstanding Stokes shifts (up to 161 nm) and quantum yields (up to 74%). Utilizing the products’ unique fluorescence response in different solvents, β-naphthothiazole 4a showed excellent aggregation-induced emission properties in 1,2-dichloroethane, which was 60 times higher than in tetrahydrofuran.
Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions
Bai, Jin,Yan, Sijia,Zhang, Zhuxia,Guo, Zhen,Zhou, Cong-Ying
supporting information, p. 4843 - 4848 (2021/06/28)
A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.