6269-47-2Relevant academic research and scientific papers
Syntheses, spectroscopic characterization, SOD-like properties and antibacterial activities of dimer copper (II) and nickel (II) complexes based on imine ligands containing 2-aminothiophenol moiety: X-ray crystal structure determination of disulfide Schiff bases
Bharti, Sulakshna,Choudhary, Mukesh,Mohan, Bharti,Rawat,Sharma,Ahmad
, p. 137 - 154 (2018)
A series of new dimer complexes of copper (II) and nickel (II) were designed and synthesized using the Schiff base ligands which was formed by the condensation of 2-aminothiophenol with 2- methoxybenzaldehyde, 3-formylbenzonitrile and 3-bromo-2-hydroxy-5-nitrobenzaldehyde, respectively. The synthesized metallic complexes were characterized by using different physicochemical and spectroscopic methods. The most plausible geometry for the 1:2 complexes appeared to be distorted square-planar or tetrahedral environments. All the synthesized metal complexes are found to be binuclear and confirmed by elemental analyses, magnetic susceptibility measurements and ESR spectroscopy. The Schiff base ligands (HL1/HL2/H2L) were coordinated to the metal ions through the ONS/SNN and/or N, S donor atoms. In order to prevent the oxidation of the thiol group during the formation of Schiff bases and its complexes, all of the reactions were carried out under an inert atmosphere of argon. The X-ray structures of the Schiff base ligands showed that in the crystalline form the SH groups were oxidized to produce a disulfide Schiff bases as a new double Schiff base ligands (L1 a/L2 a/H2La). The L1 b ligand is a bicyclic ring system of N, S-containing heterocyclic. The crystal structures of the double Schiff bases were determined by single crystal X-ray diffraction. The molar conductivity values of the complexes in DMSO implied the presence of non-electrolyte species. The SOD-like activity of Schiff bases and its complexes were investigated by NBT-DMSO assay and IC50 values were evaluated. Their biological properties have also been studied. These complexes were also tested for their in vitro antibacterial screening activities against three bacteria (Streptococcus aureus, Salmonella typhi, and Escherichia coli) comparing with the Schiff base ligands. Most of the complexes have higher antibacterial activities than those of the free Schiff bases, double Schiff bases and the control.
Investigation of Triplet States of 2-(2'-Hydroxyphenyl)benzothiazole and 2-(2'-Hydroxyphenyl)benzoxazole by Transient Absorption Spectroscopy and ab Initio Calculations
Nagaoka, Shin-ichi,Itoh, Akinori,Mukai, Kazuo,Nagashima, Umpei
, p. 11385 - 11392 (1993)
Properties of the 3(?,?*) states of 2-(2'-hydroxyphenyl)benzothiazole (HBT) and 2-(2'-hydroxyphenyl)benzoxazole (HBO) were investigated by means of transient absorption spectroscopy and ab initio calculations.When the volume fraction of ethanol in a mixed solvent of toluene and ethanol is samll, the intramolecularly proton-transferred cis-keto form of HBT predominates over the intermolecularly hydrogen-bonded trans-enol form in the triplet state.However. when the volume fraction of ethanol becomes large, the relative composition is reversed.The triplet species of HBO at 10 μs after photoexcitation contain a cis-enol form in both nonpolar and alcoholic solvents.For HBO, the cis-keto form produced immediately after photoexcitation is partly converted to the intramolecularly hydrogen-bonded cis-enol form in the triplet state whithin 10 μs.Interpretation of the solvent effect is made on the basis of the ab initio calculations for the ground state.The difference in solvent effect between HBT and HBO can be explained in terms of the hydrogen bonding involving the sulfur or oxygen atom at the 1-position.The results of the ab initio calculations for the triplet state show that the stable triplet species of HBT and HBO can be regarded as a kind of cis-keto form.This result can be explained by considering the ? electron nodal pattern of the wave function in the lowest 3(?,?*) state.
Luminescent Benzothiazole-Based Fluorophore of Anisidine Scaffoldings: a “Turn-On” Fluorescent Probe for Al3+ and Hg2+ Ions
Dhaka, Gargi,Kaur, Navneet,Singh, Jasvinder
, p. 1943 - 1948 (2017)
A new anisidine possessing benzothiaozle-based chemosensor (1) has been designed and synthesized. The chemosensor 1 was designed to provide hard base environment for ratiometric detection of comparatively less studied Al3+ ions. In CH3/su
Pentafluorophenylammonium Triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach
Datta, Arup
, p. 95 - 102 (2021/03/29)
In this work, one pot, simple and environmentally benign effective synthesis of 2-substituted benzothiazole and benzothiazoline derivatives are described in presence of PFPAT (pentafluorophenylammonium triflate) catalyst in water successfully. A series of benzothiazole derivative were synthesized by the reaction between 2-aminothiophenol and various aldehydes in good yields. Recyclability of the catalyst is observed for four times without loss of its activity in aqueous medium.
Fluorinated phosphoric acid as a versatile effective catalyst for synthesis of series of benzimidazoles, benzoxazoles and benzothiazoles at room temperature
Mathapati, Sushil R.,Patil, Komal N.,Mathakari, Sujit S.,Suryawanshi, Appasaheb W.,Jadhav, Arvind H.
, p. 538 - 547 (2021/01/21)
The present work describes synthesis of a series of benzimidazoles, benzoxazoles and benzothiazoles through the cyclization of 1, 2-phenylenediamine, 2-aminothiophenol, or 2-aminophenol with aryl, aliphatic and heteroaryl aldehydes. The present synthetic protocol is very much efficient in presence of 5 mol % fluorophosphoric acid as a catalyst in ethanol solvent at room temperature. Shorter reaction time, simple work-up technique, high yields and easy availability are specific compensations of the present synthetic approach.
A Novel Synthesis of 2-Arylbenzimidazole and 2-Arylbenzothiazole Derivatives by MnO2/MOF-199
Amouhadi, Elham,Fazaeli, Razieh,Aliyan, Hamid
, p. 495 - 502 (2021/02/09)
The main objective of this research is to develop efficient and environmentally benign heterogeneous catalysts for synthesis of 2-arylbenzimidazole and 2-arylbenzothiazoles derivatives by MnO2/MOF-199. For this purpose, a heterogeneous MnO2/MOF-199 catalyst was prepared by the solvothermal method, and the prepared catalyst was characterised by various techniques such as X-ray diffraction (XRD), scanning electron microscopy (SEM), transmission electron microscopy (TEM), BET, IR, thermogravimetric-differential thermogravimetric (TG-DTG), and temperature-programmed desorption with ammonia (NH3-TPD) analysis. The solid catalyst, with a MnO2/MOF-199 loading of 9 %, demonstrated a high catalytic activity in the synthesis of 1,2-arylbenzimidazole and 1,2-arylbenzothiazole derivatives and the catalyst could be reused for at least 5 cycles under mild conditions.
Photocatalytic green synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation over metal-free BCN: effect of crystallinity and N-B pair exposure
Cheng, Hongmei,Gao, Xue,Jiang, Heyan,Sun, Bin,Zang, Cuicui
, p. 7955 - 7962 (2021/12/27)
Porous borocarbonitride (P-BCN), with the characteristics of enhanced crystallinity and improved N-B pair exposure, was prepared with a simple KCl-assisted molten salt strategy. Efficient heterogeneous photocatalytic tandem synthesis of benzazoles from alcohol oxidation/toluene sp3C-H activation was achieved firstly over the metal-free P-BCN using visible light and the green oxidant O2, with only water as a by-product. Variouso-thio/hydroxy/aminoanilines and alcohols or toluenes could be converted to the corresponding 2-substituted benzothiazoles, benzoxazoles and benzimidazoles with good to excellent photocatalytic performance. The improved photocatalytic performance in comparison to bulk BCN should be due to the crystallinity-enhancement-induced improvement in charge separation and transmission. The increased N-B pair exposure promoted superoxide radical generation due to the electron-enriched N atoms, as well as improved oxidation ability due to the valence band constructed by the B 2p orbital. This work presents a green and efficient synthetic strategy towards benzazoles and other fine chemicalsviametal-free heterogeneous photocatalysis.
α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan
, p. 14866 - 14882 (2021/10/25)
A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).
KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C-S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles
Nandy, Anuradha,Sekar, Govindasamy
, p. 15825 - 15834 (2021/11/01)
An efficacious and mild KOtBu-promoted intramolecular C-S cross-coupling of ortho-iodothioanilides in conjunction with a catalytic quantity of phenanthroline as an additive has been described for the convenient synthesis of 2-substituted benzothiazoles. The methodology is suitable for attaining a wide variety of 2-alkyl- and 2-aryl-substituted benzothiazoles. Single-crystal XRD, DFT calculations, NMR, and UV studies suggest that halogen bonds between the units of ortho-iodothioanilides may assist in the electron transfer process.
Bimetallic Cooperative Catalysis for Decarbonylative Heteroarylation of Carboxylic Acids via C-O/C-H Coupling
Liu, Chengwei,Ji, Chong-Lei,Zhou, Tongliang,Hong, Xin,Szostak, Michal
supporting information, p. 10690 - 10699 (2021/04/09)
Cooperative bimetallic catalysis is a fundamental approach in modern synthetic chemistry. We report bimetallic cooperative catalysis for the direct decarbonylative heteroarylation of ubiquitous carboxylic acids via acyl C-O/C-H coupling. This novel catalytic system exploits the cooperative action of a copper catalyst and a palladium catalyst in decarbonylation, which enables highly chemoselective synthesis of important heterobiaryl motifs through the coupling of carboxylic acids with heteroarenes in the absence of prefunctionalization or directing groups. This cooperative decarbonylative method uses common carboxylic acids and shows a remarkably broad substrate scope (>70 examples), including late-stage modification of pharmaceuticals and streamlined synthesis of bioactive agents. Extensive mechanistic and computational studies were conducted to gain insight into the mechanism of the reaction. The key step involves intersection of the two catalytic cycles via transmetallation of the copper–aryl species with the palladium(II) intermediate generated by oxidative addition/decarbonylation.
