- Calcinized eggshell: an environmentally benign green catalyst for synthesis of 2-arylbenzothiazole derivatives
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The calcinized eggshell as an efficient and green catalyst has been prepared from chicken eggshell waste and is characterized by different analytical techniques such as FT-IR, XRD, TGA, SEM, and EDAX. A series of substituted 2-arylbenzothiazoles have been
- Borhade, Ashok V.,Uphade, Bhagwat K.,Gadhave, Anil G.
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- Synthesis and biological evaluation of 2-(3-aminophenyl)-benzothiazoles as antiproliferative and apoptosis-inducing agents
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Abstract: A series of new 2-(3-aminophenyl)-benzothiazole derivatives were synthesized and evaluated for their in vitro antiproliferative activity against various human cancer cell lines including A549, HeLa, HepG2, MCF-7, MV4-11, and DB. Among the tested
- Cheng, Zhi-Qiang,Jiang, Cheng-Shi,Muehlmann, Luis Alexandre,Song, Jia-Li,Tao, Hong-Rui,Zhang, Hua,Zhang, Juan,Zhu, Kongkai
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- Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation
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We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.
- Adimurthy, Subbarayappa,Badhani, Gaurav,Joshi, Abhisek
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p. 6705 - 6716
(2021/12/31)
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- Syntheses, characterization, and catalytic potential of novel vanadium and molybdenum Schiff base complexes for the preparation of benzimidazoles, benzoxazoles, and benzothiazoles under thermal and ultrasonic conditions
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A new ONO-tridentate Schiff base ligand (H2L) derived from 3-methoxysalicylaldehyde and nicotinic hydrazide was synthesized and characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, UV–Vis, and powder XRD studies. Then, oxovanadium(V) and dioxomolybdenum(VI) Schiff base complexes, VOL and MoO2L, were also prepared and characterized by different techniques. Moreover, the catalytic activities of both complexes were investigated for the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles under reflux conditions as well as through ultrasonic irradiation. The results revealed several advantages of this procedure, including high product yields, short reaction times, facile work-up procedure, simplicity in operation, eco-friendly reaction conditions, and green aspects by avoiding toxic catalysts and solvents. Graphic abstract: [Figure not available: see fulltext.]
- Kargar, Hadi,Kargar, Khadijeh,Fallah-Mehrjardi, Mehdi,Munawar, Khurram Shahzad
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p. 593 - 605
(2021/06/21)
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- Pentafluorophenylammonium Triflate: A Mild, Efficient and Reusable Catalyst for the Synthesis of 2-Arylbenzothiazole and 2-Arylbenzothiazoline Derivatives in a Green Chemical Approach
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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.
- Datta, Arup
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- An efficient rapid synthesis of benzoxazoles and benzothiazoles using pma.Sio2 at room temperature under heterogeneous conditions
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Treatment of 2-aminophenol (or 2-aminothiophenol) with aromatic aldehydes in the presence of phosphomolybdic acid on silica at room temperature affords the corresponding benzoxazoles (or benzothiazoles) in excellent yields (88-96%) under heterogeneous conditions. Benzoxazoles and benzothiazoles are formed in less than 10 min.
- Sudhakar, Chithaluri,Shekhar, Vanam,Shyamsunder, Manchi,Suryakumari, Adurthi,Manojkumar, Vala
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p. 583 - 587
(2021/09/30)
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- One-Pot, Borax-mediated synthesis of structurally diverse N, S-heterocycles in water
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Herein, a borax–mediated convenient and efficient strategy for the synthesis of prominent structurally diverse N, S-heterocycles such as quinazolin-4(3H)-one, benzothiadiazine 1,1-dioxide, benzothioazole, and benzoxazoles from readily available 2-aminobenzamide/2-aminobenzenesulfonamide/2-aminothiophenol/2-aminophenol with α,α,α-trihalotoluenes at 100 ℃ in water is elaborated. Upon using aldehydes instead of α,α,α-trihalotoluenes, the reactions proceed through domino fashion under the catalytic effect borax to yield 2,3-dihydroquinazolin-4(1H)-one, 3,4-dihydrothiadiazine 1,1-dioxide, and benzothiazoles in one-pot at 60 ℃. The advantages of this protocol are practical simplicity, large substrate scope, moderate to excellent yields, and the use of water as the solvent.
- Rao, Mugada Sugunakara,Hussain, Sahid
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- Ultrafine Pt nanoparticles supported on a dendrimer containing thiol groups: An efficient catalyst for the synthesis of benzimidazoles and benzothiazoles from benzyl alcohol derivatives in water
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A novel and unique platform was prepared based on a dendrimer containing thiol groups supported on nanosilica (nSTDP), and ultrafine platinum nanoparticles were synthesized and immobilized on the thiol decorated branches of nSTPD. The new catalyst, (Ptnp?nSTDP), was characterized by different techniques such as FE-SEM, TEM, ICP, XPS and DR UV-vis. This heterogeneous catalyst presented an outstanding performance for the synthesis of benzimidazole and benzothiazole derivatives through a reaction between benzyl alcohol derivatives and 2-aminothiophenol or 1,2-phenylenediamine. No requirement for the pre-reduction of catalysts and using water as a green solvent make it an individual catalyst for these reactions. Furthermore, the catalyst can be easily recovered and reused five consecutive times in the production of benzimidazoles and benzothiazoles without significant leaching of Pt and loss of its activity which illustrated the chemical stability of the catalyst during the reaction.
- Bahadori, Mehrnaz,Landarani-Isfahani, Amir,Mirkhani, Valiollah,Moghadam, Majid,Mohammadpoor-Baltork, Iraj,Nori, Zahra Zamani,Tangestaninejad, Shahram
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p. 33137 - 33147
(2020/10/02)
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- Visible light initiated amino group: Ortho -directed copper(i)-catalysed aerobic oxidative C(sp)-S coupling reaction: Synthesis of substituted 2-phenylbenzothiazoles via thia-Wolff rearrangement
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A facile amino group ortho-directed visible-light-driven copper-catalysed aerobic oxidative C(sp)-S coupling reaction of a dimer of 2-aminothiophenol with terminal alkynes was achieved. This photochemical reaction shows an excellent conversion and chemoselectivity towards the formation of C(sp)-S coupling and has been employed for a wide range of thiol dimers, and alkynes. Furthermore, the synthetic utility of the synthesized alkynyl sulfides was demonstrated as a direct method for the construction of 2-phenylbenzothiazoles from the corresponding alkynyl sulfides via "thia-Wolff rearrangement" using AgNO3 and visible light using 9-mesityl-10-methylacridinium ions (Acr+-Mes) as photoredox catalyst system.
- Anandhan, Ramasamy,Reddy, Mandapati Bhargava
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p. 3781 - 3784
(2020/04/10)
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- Nanoporous Cu doped ZnS nanoparticles an efficient photo catalyst for the chemoselective synthesis of 2-substituted azoles via C-N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence in visible light
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ZnS and Cu:ZnS nanoparticles were prepared by aqueous chemical method and characterized by several analytical tools. Nanoparticles have an average size of about ~ 18 nm and possess highly open mesopores, moderate surface area, and uniform morphology. UV–vis spectra designate that doping of Cu shifted the optical response of the ZnS nanoparticles in to a visible region. These Cu:ZnS nanoparticles were employed as a photocatalyst for chemoselective synthesis of 2-substituted azoles by the reaction of benzyl bromides and 1,2-Diaminobenzene or 2-Mercaptoaniline in visible light. Analogous experiments confirmed that the reaction were proceeds through one pot C–N arylation/ CSp3– H oxidation/ cyclization/dehydration sequence. The enhanced catalytic activity by doping could be attributed to the presence of trapping level generated by copper doping which augments the relaxation time of electron and holes so that they are easily available for the reaction. The method was also applicable for the synthesis of quinazolin-4(3H)-ones.
- Dandia, Anshu,Bansal, Sarika,Sharma, Ruchi,Kumar Mahawar, Dinesh,Rathore, Kuldeep S.,Lal Meena, Mohan,Parewa, Vijay
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- "Metal-Free" Nanoassemblies of AIEE-ICT-Active Pyrazine Derivative: Efficient Photoredox System for the Synthesis of Benzimidazoles
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Supramolecular nanoassemblies of an AIEE-ICT-active pyrazine derivative (TETPY) having strong absorption in the visible region and excellent transportability have been utilized as an efficient photoredox catalytic system for the synthesis of a variety of benzimidazoles having electron-withdrawing/electron-releasing/aliphatic groups under "metal-free"conditions. The reaction protocol involves the successful harvesting of visible light by TETPY assemblies to catalyze the coupling of o-phenylenediamine/substituted diamines and substituted aromatic/heterocyclic/aliphatic aldehydes under aerial conditions using mixed aqueous media as the reaction solvent. TETPY assemblies could activate aerial oxygen to generate superoxide for completing the vital proton abstraction step without the need for any external metal/base/oxidant. Moreover, all the products are purified by recrystallization from organic solvents. The TETPY assemblies also exhibited high efficiency in catalyzing the synthesis of 2-substituted benzothiazoles and quinazolines in excellent yields.
- Dadwal, Shruti,Kumar, Manoj,Bhalla, Vandana
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p. 13906 - 13919
(2020/11/20)
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- Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions
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The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80-95% yield) and benzothiazoles (65-98% yield) using air or O2 as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient, simple and practical than other reported methods due to the use of O2 as an oxidant, laccase as an eco-friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.
- Abdelrasoul, Amira,Ghorashi, Nadia,Moradi, Reza,Rostami, Amin,Shokri, Zahra
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p. 14254 - 14261
(2020/04/23)
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- Synthesis, characterization, and applications of novel Co(II)-pyridoxal phosphate-Schiff base/SBA-15 as a nanocatalyst for the green synthesis of benzothiazole heterocycles
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Mesoporous heterogeneous santa barbara amorphous (SBA)-15-supported cobalt complex, as a novel nanocatalyst containing N–O chelating Schiff-base ligand was successfully synthesized by the reaction of SBA-15 and Cobalt(II)-Schiff-base complex. The Co(II)-S
- Yari, Hassan,Dehkharghani, Rahebeh A.,Bardajee, Ghasem R.,Akbarzadeh-T, Niloufar
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p. 1490 - 1500
(2020/03/30)
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- Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
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Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.
- Mishra, Nidhi,Singh, Anoop S.,Agrahari, Anand K.,Singh, Sumit K.,Singh, Mala,Tiwari, Vinod K.
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supporting information
p. 389 - 399
(2019/05/06)
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- Well-Defined N-Heterocyclic Carbene-Palladium Complexes as Efficient Catalysts for Domino Sonogashira Coupling/Cyclization Reaction and C-H bond Arylation of Benzothiazole
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Well-defined and air-stable PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed palladium bis-N-heterocyclic carbene complexes have been developed for the domino Sonogashira coupling/cyclization reaction of 2-iodophenol with a variety of terminal alkynes and C-H bond arylation of benzothiazole with aryl iodides. The PEPPSI themed palladium complexes, 2a and 2b were synthesized in good yields from the reaction of corresponding imidazolium salts with PdCl2 and K2CO3 in pyridine. The new air-stable palladium-NHC complexes were characterized by NMR spectroscopy, X-ray crystallography, elemental analysis, and mass spectroscopy studies. The PEPPSI themed palladium(II) bis-N-heterocyclic carbene complexes 2a and 2b exhibited excellent catalytic activities for domino Sonogashira coupling/cyclization reaction of 2-iodophenol with terminal alkynes yielding benzofuran derivatives. In addition, the palladium complexes, 2a and 2b successfully catalyzed the direct C-H bond arylation of benzothiazole with aryl iodides as coupling partners in presence of CuI as co-catalyst.
- Yadav, Seema,Singh, Ajeet,Mishra, Isha,Ray, Sriparna,Mobin, Shaikh M.,Dash, Chandrakanta
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- Synthesis of 2-Arylbenzothiazole and 2-Arylthiazole Derivatives via a Ru-Catalyzed meta-Selective C-H Nitration Reaction
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A Ru-catalyzed meta-selective C-H nitration of 2-arylbenzothiazoles and 2-arylthiazoles has been developed. A wide range of functional groups are tolerated, providing the meta-nitrated products in good to excellent yields using Cu(NO3)2/s
- Liu, Deming,Luo, Puying,Ge, Junying,Jiang, Zilin,Peng, Yiyuan,Ding, Qiuping
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p. 12784 - 12791
(2019/08/22)
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- The ruthenium-catalyzed: Meta -selective C-H nitration of various azole ring-substituted arenes
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The efficient ruthenium-catalyzed meta-selective CAr-H nitration of azole ring substituted arenes has been developed. In this work, Ru3(CO)12 was used as the catalyst, AgNO2 as the nitro source, HPcy3+·BF4- as the ligand, pivalic acid as the additive, and DCE as the solvent, and a wide spectrum of arenes bearing thiazole, pyrazolyl or removable oxazoline directing groups were tolerated in this meta-selective CAr-H nitration, affording the nitrated products in moderate to good yields. Moreover, this study reveals a gentler and environmentally friendly way to access meta-nitration arenes compared to the traditional process.
- Zhang, Dong,Gao, Di,Cai, Jinlin,Wu, Xiaoyu,Qin, Hong,Qiao, Kai,Liu, Chengkou,Fang, Zheng,Guo, Kai
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supporting information
p. 9065 - 9069
(2019/10/28)
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- Copper supported on functionalized MCM-41 as a novel and a powerful heterogeneous nanocatalyst for the synthesis of benzothiazoles
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A new functionalized mesoporous catalyst (Cu(II)-Glycerol/MCM-41) has been synthesized as a highly efficient heterogeneous nanocatalyst for the synthesis of benzothiazoles derivatives. Powder XRD, TGA, TEM, SEM, EDX, BET, FT-IR and ICP-OES techniques are
- Noroozi Pesyan, Nader,Batmani, Hana,Havasi, Forugh
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p. 248 - 254
(2018/11/26)
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- Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase
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The invention discloses a method for synthesizing benzothiazole by microwave radiation of a benzothioamide compound in an aqueous phase. The method includes the steps: adding the benzothioamide compound into the aqueous phase under microwave conditions; performing cyclization under alkaline conditions to generate the benzothiazole. The method for preparing the benzothiazole is environmentally friendly, simple and convenient in operation, safe, cheap and efficient. Compared with the prior art, the method is applicable to a lot of functional groups, high in yield, few in by-products, simple in operation, safe, low in cost and environmentally friendly.
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Paragraph 0013; 0043
(2019/02/13)
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- Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions
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The invention discloses a method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions. According to the method, glacial aceticacid is taken as a catalyst; at solvent-free room temperature conditions, physical grinding is adopted, reaction of 2-substituted arylamines (2-mercapto arylamine, 2-aminophenol, and o-phenylenediamine) and aromatic aldehydes is carried out using physical grinding. The method is friendly to the environment, is simple in operation, is safe, is low in cost, and is high in efficiency. Compared withthe prior art, the advantages are that: the method is suitable for a large amount of functional groups, yield is high, less by-product is generated, operation is simple, the method is safe, cost is low, and the method is friendly to the environment.
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Paragraph 0062; 0144
(2019/01/21)
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- Catalyst-free synthesis of benzimidazole and benzothiazole derivatives by the cleavage of the C–C double bond of 5-arylidenepyrimidine-2,4,6-(1H,3H,5H)-triones
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Background: Benzimidazole and benzothiazole subunits exist in many biologically active molecules, natural products, and synthetic compounds. These compounds have recently gained widespread interest due to their key role in medically important compounds, such as those exhibiting anticancer activity, antimicrobial activity, inhibition of hepatitis C virus NS5B polymerase, p38 kinase inhibitory activity, and anti-inflammatory activity. Methods: 2-Substituted benzimidazole and benzothiazole derivatives have been synthesized by the condensation of 1,2-phenylenediamine or 2-aminobenzothiophenol with 5-arylidenepyrimidine-2,4,6-(1H,3H, 5H)-trione derivatives via cleavage of C-C double bond without using a catalyst in EtOH under reflux conditions. Results: We report here a very simple, novel, efficient, and catalyst-free method for the synthesis of benzimidazole and benzothiazole in good to excellent yields from the treatment of 1,2-phenylenediamine and 2-aminothiophenol with various 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione, respectively. This reaction proceeds via cleavage of a C=C double bond and elimination of barbituric acid. Conclusion: This method appears to be general for the synthesis of benzimidazoles and benzothiazoles using 5-arylidenepyrimidine-2,4,6-(1H,3H,5H)-trione derivatives containing various aromatic and heteroaromatic aldehydes such as furfural and thiophene-2-carbaldehyde with electron-withdrawing and electron-releasing groups.
- Darehkordi, Ali,Ramezani, Mahin,Rahmani, Fariba,Poor, Mahboobe Amirani
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p. 290 - 294
(2018/04/20)
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- Chitosan-SO3H: A green approach to 2-aryl/heteroaryl benzothiazoles under solvent-free conditions at room temperature
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An efficient green protocol have been developed for the synthesis of 2-aryl/heteroaryl benzothiazole derivatives by intramolecular cyclocondensation of 2-mercaptoaniline with various substituted aryl/heteroaryl aldehydes using chitosan-SO3H as an efficien
- Bathula, Surendra Bose,Khagga, Mukkanti,Venkatasubramanian, Hariharakrishnan
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p. 1512 - 1516
(2018/06/12)
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- Solid Acid Supported on Magnetic Nanoparticles as a Highly Efficient and Retrievable Catalyst for the Synthesis 2-Substituted Benzothiazoles
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The use of a recyclable heterogeneous nanomagnetic solid acid catalyst, [Fe3O4@SiO2@(CH2)3NPC–SO3H]Cl, in a simple and highly efficient synthesis of benzothiazole derivatives by the reactio
- Gorjizadeh,Sayyahi
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p. 1899 - 1903
(2018/11/24)
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- Copper containing nanosilica thioalated dendritic material: A recyclable catalyst for synthesis of benzimidazoles and benzothiazoles
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In this paper, the design and characterization of a new heterogeneous catalyst by incorporation of copper ions into the nanosilica modified by thiole–based dendrimer are reported. The prepared catalyst was characterized by FT–IR, TGA, elemental analysis,
- Zakeri, Maryam,Moghadam, Majid,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj,Pahlevanneshan, Zari
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- Sulfonic-acid-functionalized activated carbon made from tea leaves as green catalyst for synthesis of 2-substituted benzimidazole and benzothiazole
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Abstract: A simple and efficient procedure for synthesis of 2-substituted benzimidazole and benzothiazole has been developed by using sulfonic-acid-functionalized activated carbon as heterogeneous catalyst. The activated material was prepared from matured tea leaf in presence of phosphoric acid as activating agent. The final catalyst was prepared by anchoring –SO3H group on the surface of the activated carbon. The catalyst could be easily recovered and reused for more than three catalytic cycles without significant loss in catalytic activity. The catalytic performance of the catalyst was found to be superior to that of a similar catalyst prepared from montmorillonite K10. Graphical Abstract: [Figure not available: see fulltext.].
- Goswami, Mridusmita,Dutta, Mintu Maan,Phukan, Prodeep
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p. 1597 - 1615
(2017/11/17)
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- A modern and practical laccase-catalysed route suitable for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles
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Heterocyclic aromatic compounds containing an imine (C═N) bond such as benzimidazoles and benzothiazoles are important active pharmaceutical ingredients. The synthesis of 2-aryl-1H-benzimidazoles and 2-arylbenzothiazoles in good to excellent yields was ac
- Maphupha, Mudzuli,Juma, Wanyama P.,De Koning, Charles B.,Brady, Dean
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p. 39496 - 39510
(2018/12/13)
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- A 2 - (3 - aminophenyl) - benzothiazole derivatives and its preparation and use (by machine translation)
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The invention relates to the field of pharmaceutical chemistry, and in particular relates to a with anti-tumor activity of 2 - (3 - aminophenyl) - benzothiazole derivatives (formula I). Testing shows that the initial activity, the compounds of the inventi
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Paragraph 0022; 0023; 0024
(2018/11/22)
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- Method for preparing benzothiazole compound through microwave catalysis in water phase
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The invention discloses a method for preparing a benzothiazole compound through/under microwave catalysis in a water phase. A water-soluble coordination compound is used as a catalyst, and a reactionof inorganic sulfide, 2-iodoaniline and aldehyde is efficiently catalyzed through microwaves in a pure water phase. The method for preparing the benzothiazole compound is environmentally friendly, convenient to operate, safe, cheap and efficient. Compared with the prior art, the method is applied to a large quantity of functional groups, high in yield, simple to operate, safe, low in cost and environmentally friendly and produces a few byproducts.
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Paragraph 0034
(2018/05/16)
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- Elemental sulfur as a polyvalent reagent in redox condensation with: O -chloronitrobenzenes and benzaldehydes: Three-component access to 2-arylbenzothiazoles
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Sulfur was found to be a polyvalent reagent in the multicomponent redox condensation with o-chloronitrobenzenes and benzaldehydes. 2-Arylbenzothiazoles was obtained in moderate to good yields in a highly atom-economical pathway.
- Nguyen, Le Anh,Ngo, Quoc Anh,Retailleau, Pascal,Nguyen, Thanh Binh
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supporting information
p. 4289 - 4293
(2017/09/29)
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- Green and Highly Efficient Synthesis of Mono- and Bis-Benzothiazoles in the Presence of Fe(SD)3 under Ultrasound Irradiation
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A convenient, practical, green, and environmentally friendly method was developed for the synthesis of benzothiazoles from 2-aminothiophenol and various aldehydes. Bis-benzothiazoles were synthesized in high yield under mild reaction conditions. Products
- Pirbasti, Fateme Ghanbari,Mahmoodi, Nosrat Ollah
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- Anti-bacterial, catalytic and docking behaviours of novel di/trimeric imidazolium salts
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Flexible di/trimeric substituted imidazolium salts are prepared under conventional/solvent free silica supported approaches. Solid supported approaches are superior than the conventional method like environment friendly, higher yield, shorter reaction time and easy workup procedure. We have studied the catalytic activities of our synthesized di/trimeric imidazolium salts for one-pot preparation of benzoxazole derivatives under conventional/Muffle furnace conditions. We have monitored the efficiency of recycled flexible di/trimeric imidazolium salts up to fourth cycles showed excellent responses. We have studied the MIC and MBC of our di/trimeric imidazolium salts against Gram positive/negative microorganisms under micro dilution method. Nitro substituted imidazolium salts showed excellent screening responses than the unsubstituted compounds. Computer assisted docking analysis is carried out for all our synthesized compounds. The host-guest interaction via hydrogen bonding between standard and our drug molecules against various human Gram positive and negative pathogens are compared. From the docking analysis, our drug molecules showed effective interaction against test pathogens.
- Ganapathi, Pandurangan,Ganesan, Kilivelu
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p. 452 - 464
(2017/03/24)
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- NaY Zeolite Functionalized by Sulfamic Acid/Cu(OAc)2 as a Novel and Reusable Heterogeneous Hybrid Catalyst in Efficient Synthesis of Bis, Tris, and Tetrakis(indolyl)methanes, 3,4-Dihydropyrimidin-2(1H)-ones, and 2-Aryl-1H-benzothiazoles
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An efficient acid-catalyzed synthesis of some bis, tris, and tetrakis(indolyl)methanes, 3,4-dihydropyrimidin-2(1H)-ones, and 2-aryl-1H-benzothiazoles is reported using NaY zeolite functionalized by sulfamic acid/Cu(OAc)2 (NaY zeolite-NHSO3
- Kazemi, Samira,Mobinikhaledi, Akbar,Zendehdel, Mojgan
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p. 764 - 776
(2017/07/25)
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- Magnetic Co-doped NiFe2O4 Nanocomposite: A Heterogeneous and Recyclable Catalyst for the One-Pot Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazoles under Solvent-Free Conditions
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A simple and efficient procedure for the synthesis of benzimidazoles, benzoxazoles, and benzothiazoles via the condensation of o-phenylenediamine, o-aminophenol, and o-aminothiophenol with various benzaldehydes by using magnetic Co-doped NiFe2O4 nanoparticles has been developed. This nanocatalyst has advantages such as excellent product yields, solvent-free conditions, and very short reaction times. After any experiment, the magnetic nanocatalyst could be easily separated with the aid of an external magnet and reused at least four times without any loss of its catalytic performance.
- Karimian, Azam,Mohammadzadeh Kakhki, Roya,Kargar Beidokhti, Hamideh
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p. 1316 - 1325
(2017/11/22)
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- Novel Cu(0)-Fe3O4@SiO2/NH2cel as an Efficient and Sustainable Magnetic Catalyst for the Synthesis of 1,4-Disubstituted-1,2,3-triazoles and 2-Substituted-Benzothiazoles via One-Pot Strategy in Aqueous Media
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A novel, air stable, water dispersible and efficient magnetic catalyst based on copper nanoparticles onto ethylene diamine functionalized inorganic/organic composite [Cu(0)-Fe3O4@SiO2/NH2cel] has been prepared. Functionalization of inorganic/organic composite by ethylene diamine imparts desirable chemical functionality and enables the generation of active sites for the immobilization of Cu(0) nanoparticles. The novel catalyst system has been well characterized by various techniques like FTIR, TGA, XRD, SEM, HRTEM, EDX, ICP-AES, UV-Vis and VSM. Further, Cu(0)-Fe3O4@SiO2/NH2cel opens up a new avenue to introduce a very useful and efficient catalytic system for the one-pot synthesis of 1,4-disubstituted-1,2,3-triazoles via 1,3-dipolar cycloaddition of terminal acetylenes to azides, generated in situ from anilines in water at room temperature, and one-pot three component reaction of 2-iodoaniline, aldehyde and thiourea as sulphur source for the synthesis of 2-substituted-benzothiazole derivatives in water. The novel heterogeneous magnetic catalyst offers recyclability without significant deterioration in catalytic activity and can be easily recovered using an external magnet, thus making it eco-friendly and economical to perform the desired transformations.
- Bhardwaj, Madhvi,Jamwal, Babita,Paul, Satya
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p. 629 - 644
(2016/02/26)
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- Facile one-pot synthesis of 2-arylbenzothiazoles catalyzed by H3PO4/TiO2-ZrO2(1/1) under solvent-free conditions
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A highly efficient and simple protocol for the preparation of 2-arylbenzothiazoles through condensation of 2-aminothiophenol and different aldehydes in the presence of H3PO4/TiO2-ZrO2(1/1)-cetyl pyridinium bromi
- Naeimi, Hossein,Heidarnezhad, Arash
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supporting information
p. 594 - 603
(2016/06/06)
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- Copper(II)-diaminosarcophagine-functionalized SBA-15: A heterogeneous nanocatalyst for the synthesis of benzimidazole, benzoxazole and benzothiazole derivatives under solvent-free conditions
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Solvent-free organic reactions were studied over periodic mesoporous silica (SBA-15) containing a Cu(II) organometallic complex. This heterogeneous catalyst was achieved by coordination of Cu(II) ions with the diaminosarcophagine ligand and then its grafting onto the surface of SBA-15. This catalyst displayed ordered mesoporous channels, which implies an extremely high dispersion of the Cu(II) complex and the convenient diffusion of reactant molecules into the pore channels. Therefore, this catalyst can offer high activity and also facile separation or recycling when compared with its homogeneous counterparts.
- Bardajee, Ghasem Rezanejade,Mohammadi, Marzieh,Kakavand, Nahale
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- Fe3O4@SiO2/collagen: An efficient magnetic nanocatalyst for the synthesis of benzimidazole and benzothiazole derivatives
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In this project, Fe3O4@SiO2 was synthesized and combined with collagen for the preparation of Fe3O4@SiO2/collagen. It was characterized by FT-IR, 1H NMR, VSM, XRD, EDX, SEM and T
- Ghafuri, Hossein,Esmaili, Elahe,Talebi, Majid
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p. 942 - 950
(2016/08/08)
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- Catalyst-Free Synthesis of 2-Arylbenzothiazoles in an Air/DMSO Oxidant System
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A straightforward strategy for the synthesis of 2-arylbenzothiazoles from 2-aminothiophenol and aryl aldehydes in air/DMSO oxidant system has been developed. This reaction is operationally simple, proceeds without catalysts, tolerates a wide range of func
- Hu, Renhe,Li, Xiaotong,Tong, Yao,Miao, Dazhuang,Pan, Qiang,Jiang, Zengqiang,Gan, Haifeng,Han, Shiqing
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supporting information
p. 1387 - 1390
(2016/05/24)
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- Antidiabetic potential and enzyme kinetics of benzothiazole derivatives and their non-bonded interactions with α-glucosidase and α-amylase
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Benzothiazole derivatives were synthesized and their antidiabetic potential evaluated using α-glucosidase, α-amylase, non-enzymatic glycosylation of hemoglobin and advanced glycation end product inhibition assays. Compound 3l showed low IC50 va
- Puranik, Ninad V.,Puntambekar, Hemalata M.,Srivastava, Pratibha
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p. 805 - 816
(2016/03/08)
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- Acylperoxycoumarins as ortho-C?H Acylating Agent via a Palladium(II)-Catalyzed Redox-Neutral Process
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An unprecedented palladium(II)-catalyzed biomimetic aliphatic acyl (-COR) group transfer was observed from acyl-α-peroxycoumarins to the ortho C?H sites of directing arenes. Here, the C?H activation is associated with a concomitant acyl group transfer via a Pd(II)-catalyzed, redox-neutral process. While methods for ortho aroylation (-COAr) are well documented ortho acylation (-COR) processes are scarce, hence the present redox-neutral method is most ideal for o-acylation of directing substrates. (Figure presented.) .
- Ranjan Mohanta, Prakash,Banerjee, Arghya,Kumar Santra, Sourav,Behera, Ahalya,Patel, Bhisma K.
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supporting information
p. 2047 - 2052
(2016/07/16)
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- Magnetically separable nano CeO2: A highly efficient catalyst for ligand free direct C-H arylation of heterocycles
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An efficient, ligand free, nano CeO2-Fe3O4 catalyzed direct C-H arylation of heteroarenes such as benzoxazole and benzothiazole has been carried out with aryl halides in DMSO or arenediazonium salts in water. The catalyst exhibited high activity with moderate to excellent product yields under mild reaction conditions. Nano CeO2-Fe3O4 was synthesized and characterized by SEM, TEM, EDAX, XRD, FTIR, DSC-TGA, and ICP-MS analyses. The catalytic activity and stability of the catalyst were excellent, even after the ten cycle of recyclability
- Shelkar, Radheshyam S.,Balsane, Kishor E.,Nagarkar, Jayashree M.
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supporting information
p. 693 - 699
(2015/01/30)
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- An efficient desulfitative C-C cross coupling of fused thiazolidine-2-thione with boronic acids and boronic acid pinacol esters: Formation of fused thiazoles
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An efficient Pd(0)-catalyzed Cu(i)-mediated desulfitative C-C cross-coupling of benzo-fused thiazolidine-2-thione with boronic acids under neutral Liebeskind-Srogl conditions is described. The desulfitative cross coupling of boronic acid pinacol esters has also been demonstrated with fused thiazolidine-2-thione under basic conditions to afford fused thiazoles with good to excellent yields.
- Rajaguru, Kandasamy,Mariappan, Arumugam,Manjusri, Ramachandran,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
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p. 86832 - 86839
(2015/11/03)
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- Trichloroisocyanuric Acid/Triphenylphosphine-Mediated Synthesis of Benzimidazoles, Benzoxazoles, and Benzothiazoles
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A new and efficient method for preparation of benzimidazoles, benzoxazoles, and benzothiazoles from reactions of different carboxylic acids with o-phenylenediamine, o-aminophenol, and o-aminothiophenol in the presence of triphenylphosphine/trichloroisocyanuric acid system is presented. The desired products have been characterised on the basis of spectral (infrared, NMR, mass spectrometry) data, and the mechanism of their formation is proposed. The remarkable advantages are the inexpensive and readily available reagent, simple procedure, mild conditions, and good-to-excellent yields.
- Rezazadeh, Soodabeh,Akhlaghinia, Batool,Razavi, Nasrin
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p. 145 - 155
(2015/05/05)
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- Elemental sulfur mediated decarboxylative redox cyclization reaction of o -chloronitroarenes and arylacetic acids
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A decarboxylative redox cyclization strategy has been developed for the synthesis of 2-substituted benzothiazoles by the reaction of o-chloronitroarenes and arylacetic acids in the presence of elemental sulfur/N-methylmorpholine under metal- and solvent-free conditions.
- Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
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supporting information
p. 976 - 978
(2015/03/30)
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- Piperazinylpyrimidine modified MCM-41 for the ecofriendly synthesis of benzothiazoles by the simple cleavage of disulfide in the presence of molecular O2
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This is the first report of a sustainable and toxic metal free synthesis of benzothiazoles by the cleavage of ortho-aminothiophenol disulfide using a silica-supported heterogeneous catalyst in water in the presence of molecular O2 as a stoichiometric oxidant. For this purpose a new heterogeneous catalyst (MCM-PP) was synthesized by post synthesis grafting of 2-(piperazin-1-yl)pyrimidine functionalized organosilane onto MCM-41 mesoporous silica and it was characterized by BET surface area analysis, SAXRD, UHR TEM, CHN analysis, 13C CP MAS and 29Si MAS NMR. The reaction requires two different catalytic functions, i.e., an acidic one which is given by MCM-41 and a basic one, given by the organic base moiety anchored to the MCM-41. The greenness of the process was assured as water was exploited as the reaction medium and O2 from air as the stoichiometric oxidant. Furthermore the leaching of the active site can also be avoided as the organic moieties are covalently attached to the inorganic support. Standard leaching experiments proved that the reaction was heterogeneous with this recyclable catalyst.
- Ray, Suman,Das, Paramita,Banerjee, Biplab,Bhaumik, Asim,Mukhopadhyay, Chhanda
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p. 72745 - 72754
(2015/09/15)
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- Synergism in semiconducting nanocomposites: Visible light photocatalysis towards the formation of C-S and C-N bonds
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A simple, facile and visible light driven photochemical synthesis of 2-substituted benzothiazoles and 2-substituted benzimidazoles is achieved with CdSe nanocomposites as a photocatalyst. These nanocomposites are prepared by the molecular self assembly of 2-3 nm sized zinc blende CdSe phase within the layers of montmorillonite (MMT) through intercalation forming lamellar structure. CdSe/MMT exhibits excellent photocatalytic activity towards the synthesis of benzazoles using aliphatic, aromatic and heterocyclic aldehydes with better yields, and the efficiency is retained up to five cycles. XRD, XPS and Raman analyses of fresh and used CdSe/MMT reveal the passivation of structural defects due to the formation of a thin layer of CdO on the photocatalyst surface. The mixed phase of CdSe-CdO facilitates the generation of a hetero-junction on the CdSe/MMT surface, which is beneficial for photostability and sustainability. This process is also efficient under solar light and provides easy product isolation on the gram scale. Thus, it may be regarded as a greener methodology for the synthesis of bioactive scaffolds with excellent yields and high chemoselectivity using a tailor-made photocatalyst.
- Wade, Anil R.,Pawar, Hari R.,Biware, Megha V.,Chikate, Rajeev C.
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supporting information
p. 3879 - 3888
(2015/07/15)
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- Lithium bromide catalyzed efficient and convenient synthesis of 2-arylbenzothiazole derivatives
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A new and efficient protocol was developed for synthesis of benzothiazoles using lithium bromide as catalyst under environmentally friendly conditions. The developed synthetic protocol represents a novel and very simple route for preparation of 2-substitu
- Gill, Charansingh H.,Nikam, Mukesh D.,Mahajan, Pravin S.,Chate, Asha V.,Dabhade, Sanjay K.,Badadhe, Pravin V.
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p. 7509 - 7516
(2015/02/19)
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- Magnetic ionic liquid [bmim][FeCl4] as an efficient catalyst for the synthesis of 2-Aryl benzimidazoles and 2-aryl benzothiazoles derivatives
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The magnetic ionic liquid (MIL) 1-butyl-3-methylimidazolium tetrachloro ferrate(III) ([bmim][FeCl4 ]) sufficiently catalyzes the one-pot condensation of 1,2 diaminobenzene or 2-aminobenzenethiol with different aromatic aldehydes producing benzimidazoles a
- Sayyahi, Soheil,Shabani, Sara,Ghasemi, Sara,Azin, Atena,Hasani, Seyyed Morteza
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p. 1773 - 1778
(2016/01/26)
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- Synthesis of 2-substituted benzimidazoles and benzothiazoles using Ag2CO3/Celite as an efficient solid catalyst
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An efficient and simple approach for the synthesis of 2-substituted benzimidazoles and benzothiazoles through a coupling of 1,2-phenylenediamines and 2-aminothiophenols with variety of aryl aldehydes in ethanol at 70 °C using Ag2CO3/Celite as solid catalyst is described. The procedure features short reaction time, excellent yields and simple workup.
- Soleimani, Ebrahim,Khodaei, Mohammad Mehdi,Yazdani, Hossein,Saei, Parisa,Zavar Reza, Javad
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p. 1281 - 1285
(2015/06/02)
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- Nano-Titania-Supported Sulfonic-Acid-Catalyzed Synthesis of 2-Arylbenzothiazole Derivatives under Solvent Free Conditions
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Nano-titania-supported sulfonic acid (n-TSA) has been used as an efficient, inexpensive and reusable heterogeneous nano catalyst for synthesis of 2-arylbenzothiazole derivatives under solvent free condition. The reaction works very well, with good to exce
- Amoozadeh, Ali,Azadeh, Rahmat Allah,Rahmani, Salman,Salehi, Mehdi,Kubicki, MacIej,Dutkiewicz, Grzegorz
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p. 1874 - 1883
(2015/12/12)
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