- Orange phosphorescent Ir(III) complexes consisting of substituted 2-phenylbenzothiazole for solution-processed organic light-emitting diodes
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Orange phosphorescent iridium(III) complexes, (DMBT)2Ir(acac) and (TBT)2Ir(acac), based on either 2-(3,4-dimethylphenyl)benzo[d]thiazole (DMBT) or 2-(4-(trimethylsilyl)phenyl)benzo[d]thiazole (TBT) as the cyclometalated main ligands
- Jang, Jae-Ho,Park, Hea Jung,Park, Jeong Yong,Kim, Hee Un,Hwang, Do-Hoon
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- Synthesis of benzimidazoles/benzothiazoles by using recyclable, magnetically separable nano-Fe2O3 in aqueous medium
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An efficient, simple, ecofriendly and cost-effective method has been developed for the synthesis of benzimidazole/benzothiazole derivatives by a two-component reaction, involving 1,2-diamino benzene/2-amino thiophenol and substituted aromatic aldehydes us
- Kommula, Dileep,Madugula, Sri Rama Murty
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- Microwave-induced solvent-free synthesis of 2-arylbenzothiazoles using p-TsOH
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A simple and efficient procedure has been developed for the synthesis of 2-arylbenzothiazoles by a one-pot reaction of o-aminothiophenol with β-chlorocinnamaldehydes using p-TsOH under microwave irradiation.
- Paul, Satya,Gupta, Mukta,Gupta, Rajive
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- An efficient palladium catalyzed synthesis of 2-arylbenzothiazoles
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A novel and convergent palladium catalyzed synthesis of 2-arylbenzothiazoles has been investigated. The key step in the synthesis is a Suzuki biaryl coupling of 2-bromobenzothiazole with aryl boronic acids to provide a variety of 2-arylbenzothiazole derivatives in good yield. The synthetic utility of this methodology is demonstrated by the synthesis of 2-(4-aminophenyl)-6-methoxybenzothiazole, a PET probe precursor for the in vivo imaging of Alzheimer's disease.
- Majo, Vattoly J.,Prabhakaran, Jaya,Mann, J. John,Kumar, J. S. Dileep
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- Graphene oxide-catalyzed synthesis of benzothiazoles with amines and elemental sulfur via oxidative coupling strategy of amines to imines
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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.
- He, Haiping,Duan, Dehao,Li, Hong,Wei, Yifei,Nie, Liang,Tang, Bo,Wang, Hanyu,Han, Xiaowei,Huang, Panpan,Peng, Xiangjun
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- Room temperature HFIP/Ag-promoted palladium-catalyzed C–H functionalization of benzothiazole with iodoarenes
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A versatile synthetic protocol involving the room temperature direct arylation of benzothiazole with a wide variety of iodoarenes under Ag-promoted Pd-catalyzed conditions in HFIP as the reaction solvent has been presented. A sequential HFIP-promoted sele
- Bhujbal, Yuvraj,Gharpure, Santosh J.,Kapdi, Anant R.,Kommyreddy, Saidurga Prasad,Kori, Santosh,Vadagaonkar, Kamlesh
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supporting information
p. 847 - 850
(2022/02/01)
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- Fast and high-efficiency synthesis of 2-substituted benzothiazoles via combining enzyme catalysis and photoredox catalysis in one-pot
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An efficient and green method, combining enzymatic and visible-light catalysis for synthesis of the widely applicable 2-substituted benzothiazoles, has been developed. This method features a relay catalysis protocol consisting of biocatalytic promiscuity
- Yang, Zeng-Jie,Gong, Qing-Tian,Yu, Yuan,Lu, Wei-Fan,Wu, Zhe-Ning,Wang, Na,Yu, Xiao-Qi
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supporting information
(2021/01/14)
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- Ultrasound-assisted efficient and green synthesis of 2-substituted benzothiazoles under solvent-free condition using recyclable sulfated tungstate
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Sulfated tungstate catalyzed an efficient and ecofriendly protocol has been described for the synthesis of 2-substituted benzothiazoles. The corresponding benzothiazoles were obtained using a condensation reaction of 2-aminothiophenol with various aldehydes under ultrasound irradiation at room temperature. Various functional groups on the 2-aminothiophenol as well as on the aldehydes were tolerated to provide 2-substituted benzothiazoles derivatives in excellent yields. The faster reaction rate, solvent-free or mild reaction conditions, wide functional group compatibility, excellent yields, easy work-up procedure, and excellent catalyst recyclability are the advantages of this protocol. These advantages make this process more practicable, cost-effective, and environmentally benign.
- Pise, Ashok S.,Ingale, Ajit P.,Dalvi, Navnath R.
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supporting information
p. 3629 - 3641
(2021/10/12)
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- Ionic liquid-immobilized hybrid nanomaterial: an efficient catalyst in the synthesis of benzimidazoles and benzothiazoles via anomeric-based oxidation
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Abstract: In this study, a novel ionic liquid immobilized on silica-coated cobalt-ferrite magnetic nanoparticles. This novel hybrid nanostructure (CoFe2O4@SiO2@PAF-IL) was characterized by various microscopic and spectroscopic techniques including Fourier transformation infrared spectroscopy (FT–IR), X-ray powder diffraction (XRD), field emission scanning electron microscopy (SEM), the electron-dispersive X-ray spectroscopy (EDS), vibrating sample magnetometer (VSM), and thermogravimetric analysis (TGA/DTG). The catalytic activity of prepared nanomaterial was considered in the synthesis of the benzothiazole and benzimidazole derivatives. This method has several advantages such as good to excellent yields, short reaction times, solvent-free and environmentally-benign conditions, and simple work-up. Besides, nanocatalyst can be easily separated from the reaction mixture with the external magnetic field and reused several times without any loss of its catalytic activity. Graphic abstract: [Figure not available: see fulltext.].
- Bodaghifard, Mohammad Ali,Shafi, Saeideh
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p. 677 - 687
(2020/09/18)
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- Synthesis of benzothiazoles using fluorescein as an efficient photocatalyst under visible light
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This work reports a novel and efficient method for the synthesis of benzothiazoles using 2-aminothiophenol derivatives in conjunction with aromatic aldehyde as starting materials via visible-light-induced condensation cyclization. Utilizing fluorescein as the photocatalyst and blue LED lamp as the light source, the reaction proceeds in the presence of a molecular oxygen atmosphere without the need for metal catalyst or an additional oxidant. Significantly, this method exhibits good tolerance in substrates, and a variety of 2-aminothiophenol derivatives and aromatic aldehyde are amenable to producing the corresponding benzothiazoles in high to excellent yields.
- Chen, Haodong,Lei, Mayan,Liu, Chunyan,Sun, Wuji,Wang, Kaixuan,Wang, Xueyao,Zhong, Qidi
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- Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions
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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.
- Bai, Jin,Yan, Sijia,Zhang, Zhuxia,Guo, Zhen,Zhou, Cong-Ying
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supporting information
p. 4843 - 4848
(2021/06/28)
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- ZnO-NPs catalyzed condensation of 2-aminothiophenol and aryl/alkyl nitriles: Efficient green synthesis of 2-substituted benzothiazoles
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The synthesis of 2-substituted benzothiazoles has been described using ZnO-nanoparticles as a catalyst. The condensation of 2-aminothiophenol and aryl/alkyl nitriles resulted in the formation of various 2-substituted benzothiazoles under solvent-free reaction conditions. The library of 2-substituted benzothiazoles has been synthesized in good to excellent yield. The reaction has shown a wide range of functional group compatibility for both varyingly substituted 2-aminothiophenols and nitriles. The protocol has many advantages such as faster reaction rate, mild reaction conditions, various functional group compatibility, excellent yield, solvent-free reaction conditions, easy recovery of materials, and excellent catalyst recyclability, among others. The various advantages of this protocol make it a more feasible, economical, and environmentally benign process.
- Dhawale, Kiran D.,Ingale, Ajit P.,Shinde, Sandeep V.,Thorat, Nitin M.,Patil, Limbraj R.
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p. 1588 - 1601
(2021/03/18)
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- Heterocyclic reaction inducted by Br?nsted–Lewis dual acidic Hf-MOF under microwave irradiation
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Use of green chemistry and alternative strategies has been explored to prepare diverse organic derivatives. The combination between heterogeneous catalyst, environmentally benign reaction and high-yielding methods is gaining momentum. Herein, a defective 6-connected Hf-MOF, named Hf-BTC, was efficiently synthesized and characterized for the heterogeneous catalysis under microwave irradiation. The MOF features including structural defect, porosity, acidity, and stability was analyzed by powder X-ray diffraction, N2 sorption isotherms, acid-base titration, and thermal gravimetric analysis. In the catalytic studies, the Br?nsted-Lewis dual acidic Hf-BTC was efficiently applied for the synthesis of the heterocyclic compounds via the microwave-assisted cycloaddition and condensation reactions. The reactions proceeded smoothly in the presence of the Hf-MOF with a broad scope of substrates provided the expected products in high to excellent yields (up to 99 %) for few minutes and the catalyst could be easily recycle over many consecutive reactions without loss of its reactivity and structure.
- Nguyen, Linh Ho Thuy,Nguyen, Trang Thi Thu,Dang, Minh-Huy Dinh,Tran, Phuong Hoang,Doan, Tan Le Hoang
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- Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation
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A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed. Upon irradiation with visible light, substrates undergo dehalogenative cyclization to 2-aryl benzothiazoles with high efficiency and selectivity. This photocyclization exhibits a high tolerance to various functional groups, is applicable for the synthesis of 2-alkyl benzothiazoles, and is easy to set up for gram-scale reaction.
- Wang, Hao,Wu, Qi,Zhang, Jian-Dong,Li, Hai-Yan,Li, Hong-Xi
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supporting information
p. 2078 - 2083
(2021/04/05)
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- Preparation method of benzothiazole phosphate compound
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The invention discloses a preparation method of a benzothiazole phosphate compound. Under the irradiation of visible light, N-(2-bromophenyl) alkyl thioamide such as N-(2-bromophenyl) alkyl thioamide derivatives and the like are used as raw materials, sodium phosphate is used as alkali, a series of 2-substituted alkyl benzothiazole derivatives are smoothly synthesized, and further, under the irradiation of visible light, the benzothiazole phosphate compound is prepared through reaction with diethyl phosphate, and the benzothiazole phosphate compound has the calcium antagonist capability.
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Paragraph 0028-0030
(2021/06/13)
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- Method for preparing benzothiazole compound from visible light promoted N-(2-bromophenyl) thioamide
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The invention discloses a method for preparing a benzothiazole compound from N-(2-bromophenyl) thioamide under the promotion of visible light. Specifically, under the protection of inert gas, according to the molar ratio of N-(2-bromophenyl) thioamide to inorganic base being 1: 0.5, reactants are added into a reaction container provided with a stirring device, then dimethyl sulfoxide is added, and stirring reaction is carried out for 2-24 hours at room temperature under the irradiation of visible light to obtain the benzothiazole compound. Under the condition of not adding any photosensitizer or transition metal catalyst, sodium phosphate is used as alkali, and under the irradiation of a 45W household compact fluorescent lamp, a series of intramolecular cross-coupling reactions of N-(2-bromophenyl) thioamide are realized. In addition, the benzothiazole compound can be obtained with high yield. The whole process is green, efficient and easy to operate, and the method is a good method for synthesizing the benzothiazole compound.
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Paragraph 0067-0069
(2021/06/22)
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- Br?nsted Acid Mediated Nucleophilic Functionalization of Amides through Stable Amide C?N Bond Cleavage; One-Step Synthesis of 2-Substituted Benzothiazoles
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We have developed a Br?nsted acid mediated synthetic method to directly cleave stable amide C?N bonds by a variety of alcohol and amine nucleophiles. Reverse reactivity was observed and alcoholysis of amides by activated primary and secondary benzylic, and propargylic alcohols have been achieved instead of the expected nucleophilic substitution of alcohols. As an application, 2-substituted benzothiazole derivatives have been synthesized in one pot employing 2-aminothiophenol as nucleophile.
- Biswas, Srijit,Biswas, Subrata,Duari, Surajit,Elsharif, Asma M.,Maity, Srabani,Roy, Arnab
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supporting information
p. 3569 - 3572
(2021/07/22)
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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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- Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines
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This study aims to develop green and sustainable advanced synthetic methods based on redox cyclization. Elemental sulfur is shown to promote the efficient synthesis of 2-substituted benzothiazoles from 2,2′-dinitrodiphenyl disulfides and benzylamines via redox cyclization in the absence of transition-metal catalysts and solvents. The 2-substituted benzothiazoles are obtained in good to excellent yields. This synthetic methodology is highly atom-economical and does not require any external oxidizing and/or reducing agents.
- Teramoto, Masahiro,Imoto, Mitsutaka,Takeda, Motonori,Mizuno, Takumi,Nomoto, Akihiro,Ogawa, Akiya
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p. 2485 - 2493
(2021/04/15)
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- α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
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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).
- Huang, Jian,Chen, Wei,Liang, Jiazhi,Yang, Qin,Fan, Yan,Chen, Mu-Wang,Peng, Yiyuan
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p. 14866 - 14882
(2021/10/25)
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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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- "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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- Sulfamic acid-catalyzed conversion of o-aminothiophenol and aromatic aldehydes to 2-arylbenzothiazoles
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Non-metallic, non-toxic, and cheap sulfamic acid was used as a catalyst for the synthesis of 2-arylbenzothiazole from o-aminothiophenol and aromatic aldehydes bearing electron-donating or electron-withdrawing groups. The sulfamic acid catalyst can be reus
- Shi, Chunjie,Song, Renyuan,Wang, Guangrong,Yu, Xiaofeng
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p. 871 - 879
(2020/09/09)
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- Straightforward synthesis of benzoxazoles and benzothiazoles via photocatalytic radical cyclization of 2-substituted anilines with aldehydes
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Eosin Y-catalyzed one-pot coupling and cyclization of o-substituted anilines with aldehydes to form benzoxazoles and benzothiazoles under mild condition has been developed. The reaction scope was broadly tolerant of various 2-substituted anilines and aldehydes. The desired products were obtained in high yields with the use of eosin Y as a photocatalyst under a substantial refinement of reaction conditions in comparison with previous literature. Based on the experimental results observed, a plausible mechanism involving a radical process has been proposed.
- Le, Hao Anh Nguyen,Nguyen, Long Hoang,Nguyen, Quynh Nhu Ba,Nguyen, Hai Truong,Nguyen, Khang Quoc,Tran, Phuong Hoang
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- Benzothiazole Synthesis: Mechanistic Investigation of an in Situ-Generated Photosensitizing Disulfide
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The use of a visible light absorbing intermediate as a photosensitizer makes a chemical process simple and sustainable, obviating the need for the use of chemical additives. Herein, the formation of a photosensitizing disulfide in benzothiazole synthesis from 2-Aminothiophenol and aldehydes was proposed and confirmed through in-depth mechanistic studies. A series of photophysical and electrochemical investigations revealed that an in situ-generated disulfide photosensitizes molecular oxygen to generate the key oxidants, singlet oxygen and superoxide anion, for the dehydrogenation step.
- Hwang, Ho Seong,Lee, Sumin,Han, Sung Su,Moon, Yu Kyung,You, Youngmin,Cho, Eun Jin
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p. 11835 - 11843
(2020/10/23)
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- Preparation method of 2-aryl benzothiazole compound
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The invention discloses a preparation method of a 2-arylbenzothiazole compound, which comprises the following steps: adding a reaction substrate 2-aminothiophenol and ketonic acid(or aldehyde) into adeep eutectic solvent, magnetically stirring in an oil bath pot at 60-90 DEG C, and carrying out after-treatment after the reaction is finished to obtain the 2-arylbenzothiazole compound, wherein a deep eutectic solvent is a reaction solvent, and other catalysts are not needed. The method is simple to operate, mild in reaction condition, efficient in reaction, high in atom economy, few in byproducts and green and environment-friendly in reaction process, and has popularization and application values.
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Paragraph 0116; 0119-0120
(2020/05/09)
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- Method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide
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The invention discloses a method for preparing 1, 3-benzothiazole derivative through efficient catalysis of potassium tert-butoxide. According to the method, a 1-phenyl-3-butyne-2-ketone compound andan o-aminothiophenol compound are taken as raw materials, potassium tert-butoxide is taken as a catalyst and tert-butyl alcohol is taken as a solvent to prepare the 1, 3-benzothiazole derivative at high efficiency and high yield. According to the method, no metal catalyst is used, the method is environmentally friendly, reaction conditions are mild, operation is easy, the 1, 3-benzothiazole derivative can be obtained only by conducting simple column chromatography separation on a product obtained after the reaction is finished, a new green and efficient way is developed for preparation of the1, 3-benzothiazole derivative, and certain application prospects are achieved.
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Paragraph 0007; 0014-0019; 0038-0041
(2020/02/10)
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- Photoinduced Heterogeneous C?H Arylation by a Reusable Hybrid Copper Catalyst
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Heterogeneous copper catalysis enabled photoinduced C?H arylations under exceedingly mild conditions at room temperature. The versatile hybrid copper catalyst provided step-economical access to arylated heteroarenes, terpenes and alkaloid natural products with various aryl halides. The hybrid copper catalyst could be reused without significant loss of catalytic efficacy. Detailed studies in terms of TEM, HRTEM and XPS analysis of the hybrid copper catalyst, among others, supported its outstanding stability and reusability.
- Choi, Isaac,Müller, Valentin,Lole, Gaurav,K?hler, Robert,Karius, Volker,Vi?l, Wolfgang,Jooss, Christian,Ackermann, Lutz
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supporting information
p. 3509 - 3514
(2020/03/03)
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- Iodine-catalyzed convergent aerobic dehydro-aromatization toward benzazoles and benzazines
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An iodine-catalyzed aerobic dehydro-aromatization has been developed, providing straightforward and efficient access to various benzoazoles and benzoazines. The present transition-metal-free protocol enables the dehydro-aromatization of tetrahydrobenzazoles and tetrahydroquinolines with molecular oxygen as the green oxidant, along with some other N-heterocycles. Hence, a broad range of heteroaromatic compounds are generated in moderate to good yields under facile reaction conditions.
- Chen, Shanping,Deng, Guo-Jun,Jiang, Pingyu,Ni, Penghui,Tuo, Xiaolong,Wang, Xiaodong
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p. 8348 - 8351
(2020/03/11)
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- Synthesis of Benzothiazoles via Photooxidative Decarboxylation of α-Keto Acids
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Herein, synthesis of benzothiazoles via decarboxylative cross-coupling between α-keto acids and 2-aminothiophenols under blue LED irradiation without using any photocatalyst or metal at room temperature is described. The formation of benzothiazole is driven by the EDA (electron donor-acceptor) complex formed between α-keto acid and 2-aminothiophenol. This methodology gives easy access to 2-substituted and -unsubstituted benzothiazoles in moderate to good yields. α-Keto acids and 2-aminothiophenols bearing different functional groups were easily transformed under the given conditions. (Figure presented.).
- Monga, Aparna,Bagchi, Sourav,Soni, Raj Kumar,Sharma, Anuj
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supporting information
p. 2232 - 2237
(2020/03/04)
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- Preparation method of heterogeneous sustainable catalytic benzothiazole derivatives (by machine translation)
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The invention relates to a preparation method of a heterogeneous sustainable catalytic benzothiazole derivative. The chemical structural formula is that, the substituent R1 is any one of a substituted aryl group, a substituent position and a conjugation position, R2 is any one of an aromatic substituted aryl group, a substituent position and a conjugation position are not fixed. The synthesis method is characterized in that Cu-MOF derivative materials are added, reaction is carried out by O-aminophenol and benzyl alcohol by one-pot method, and the by-products are produced in the form of water. To the method, the catalyst can be separated and put into the next reaction after the reaction, and the catalytic effect remains unchanged. The catalyst Cu-MOF derived material is a catalyst obtained by carbonizing HKKKSUT-1. The reaction makes the reaction green more further. The utility model provides an efficient. The invention relates to a pollution-free synthesis method for benzothiazole derivatives. (by machine translation)
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Paragraph 0030-0031
(2021/01/15)
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- A novel ternary GO@SiO2-HPW nanocomposite as an efficient heterogeneous catalyst for the synthesis of benzazoles in aqueous media
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A new solid acid catalyst, consisting of 12-phosphotungstic heteropoly acid (HPW) supported on graphene oxide/silica nanocomposite (GO@SiO2), has been developed via immobilizing HPW onto an amine-functionalized GO/SiO2 surface through coordination interaction (GO@SiO2-HPW). The GO@SiO2-HPW nanocomposite was characterized by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), and powder X-ray diffraction (XRD). The prepared nanocomposite could be dispersed homogeneously in water and further used as a heterogeneous, reusable, and efficient catalyst for the synthesis of benzimidazoles and benzothiazoles by the reaction of 1,2-phenelynediamine or 2-aminothiophenol with different aldehydes.
- Habibzadeh, Setareh,Firouzzadeh Pasha, Ghasem,Tajbakhsh, Mahmood,Amiri Andi, Nasim,Alaee, Ehsan
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p. 934 - 944
(2019/06/13)
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- Silica-supported zinc chloride (ZnCl2/SiO2)-induced efficient protocol for the synthesis of N-sulfonyl imines and 2-Arylbenzothiazole
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A straightforward strategy for the synthesis of N-sulfonyl imine derivatives from sulfonamides and aryl aldehydes utilizing Silica-supported zinc chloride (ZnCl2/SiO2, silzic) as a catalyst under solvent-free conditions has been developed. 2-Arylbenzothiazole derivatives were also synthesized by the reaction of 2-aminothiophenol with aryl aldehydes under the same conditions. This procedure has advantages of high yields, mild reaction condition, simple procedure, low cost, and simplicity of workup. The catalyst has the same efficiency on its reuse up to three times.
- Soliman, Hanan A.,El-Shahat, Mahmoud,Soliman, Abdel-Ghany
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p. 584 - 591
(2019/07/31)
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- I2/TBHP-Mediated tandem cyclization and oxidation reaction: Facile access to 2-substituted thiazoles and benzothiazoles
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The efficient synthesis of 2-substituted thiazoles and benzothiazoles has been accomplished employing readily available cysteine esters and 2-aminobenzenethiols as N and S sources. The reaction proceeds under an I2/TBHP system and involves a on
- Liu, Li,Tan, Chen,Fan, Rong,Wang, Zihan,Du, Hongguang,Xu, Kun,Tan, Jiajing
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supporting information
p. 252 - 256
(2019/01/10)
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- Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer
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Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.
- Xu, Ze-Ming,Li, Hong-Xi,Young, David James,Zhu, Da-Liang,Li, Hai-Yan,Lang, Jian-Ping
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supporting information
p. 237 - 241
(2019/01/10)
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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; 0051
(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; 0132
(2019/01/21)
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- Synthesis of 2-substituted benzothiazoles via the Br?nsted acid catalyzed cyclization of 2-amino thiophenols with nitriles
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A convenient and efficient method for the synthesis of 2-substituted benzothiazoles from simple and readily available 2-amino thiophenols and nitriles is described. The Br?nsted acid-catalyzed cyclization reaction was performed under metal and solvent-free conditions.
- Yu, Xiaoqiang,Yin, Qing,Zhang, Zhiheng,Huang, Tianyu,Pu, Zichao,Bao, Ming
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supporting information
p. 1964 - 1966
(2019/06/27)
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- TBHP/KI-Promoted Annulation of Anilines, Ethers, and Elemental Sulfur: Access to 2-Aryl-, 2-Heteroaryl-, or 2-Alkyl-Substituted Benzothiazoles
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An efficient TBHP/KI-promoted annulation of anilines with ethers and elemental sulfur has been developed through the selective C-O bond cleavage of ethers under transition-metal-free conditions. A wide range of 2-aryl-, 2-heteroaryl-, and 2-alkyl-substituted benzothiazoles were easily prepared with satisfactory yields and good functional group compatibility.
- Zhang, Jie,Zhao, Xin,Liu, Ping,Sun, Peipei
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p. 12596 - 12605
(2019/10/11)
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- Copper-Catalyzed Benzylic C—H Functionalization, Oxidation and Cyclization of Methylarenes: Direct Access to 2-Arylbenzothiazoles
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The direct C—H functionalization of methylarenes is of great significance. Herein, a copper-catalyzed oxidative C—N/C—S bond formation through benzylic C(sp3)—H functionalization, oxidation and cyclization of methylarenes is reported. Various 2-arylbenzothiazoles have been synthesized in moderate to excellent yields with readily available o-iodoaniline, potassium sulfide, and methylarenes as raw materials.
- Yu, Wentao,Wu, Wanqing,Jiang, Huanfeng
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p. 1158 - 1166
(2019/10/22)
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- Di- tert-butyl Peroxide-Mediated Radical C(sp2/sp3)-S Bond Cleavage and Group-Transfer Cyclization
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A novel strategy of cascade radical C(sp2/sp3)-S bond cleavage and group-transfer cyclization is disclosed. Triggered by alkyl radicals, varieties of 2-isocyanoaryl thioethers containing aliphatic, aryl, and heteroaromatic groups can be cleaved and precisely reinstalled to give benzothiazole derivatives. Mechanistic studies reveal that the cascade reaction undertakes an intermolecular pathway, and the inner radical sources (R radicals) exhibit high priority over those of methyl radical origin from di-tert-butyl peroxide.
- Luo, Kai,Yang, Wen-Chao,Wei, Kai,Liu, Yue,Wang, Jun-Ke,Wu, Lei
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p. 7851 - 7856
(2019/10/11)
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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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- 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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- 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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- Phosphonium acidic ionic liquid: An efficient and recyclable homogeneous catalyst for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles
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A highly efficient and green strategy for the synthesis of 2-Arylbenzoxazoles, 2-Arylbenzimidazoles, and 2-Arylbenzothiazoles catalyzed by phosphonium acidic ionic liquid has been developed via the condensation of o-Aminophenol, o-phenylenediamines, and o-Aminothiophenol, respectively, with aldehydes. The reaction has a good yield, the broad substrate scope, and mild condition. Triphenyl(butyl-3-sulphonyl)phosphonium toluenesulfonate catalyst was easily obtained from cheap and available starting materials through a one-pot synthesis. Its structure was identified by 1H NMR, 13C NMR, 31P NMR, and FT-IR techniques. Other properties including thermal stability and acidity were determined by TGA and Hammett acidity function method. Interestingly, the catalyst can maintain its constantly outstanding performance till the fourth recovery.
- Nguyen, Quang The,Thi Hang, Anh-Hung,Ho Nguyen, Thuy-Linh,Nguyen Chau, Duy-Khiem,Tran, Phuong Hoang
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p. 11834 - 11842
(2018/04/05)
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- N-Heterocyclic Carbene (NHC)-Catalyzed One-Pot Aerobic Oxidative Synthesis of 2-Substituted Benzo[ d ]oxazoles, Benzo[ d ]thiazoles and 1,2-Disubstituted Benzo[ d ]imidazoles
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N-Heterocyclic carbene (NHC), generated in situ from easily available N-heterocyclic imidazolium salt with air as terminal oxidant, has successfully been utilized as a cheap and efficient catalyst for one-pot aerobic oxidative synthesis of 2-arylbenzo[ d ]oxazoles, 2-substituted benzo[ d ]thiazoles, and 1,2-disubstituted benzo[ d ]imidazoles.
- Zhou, Quan,Liu, Shu,Ma, Ming,Cui, He-Zhen,Hong, Xi,Huang, Shuang,Zhang, Jing-Fan,Hou, Xiu-Feng
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supporting information
p. 1315 - 1322
(2018/03/10)
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- Metallaphotoredox-Mediated Csp2-H Hydroxylation of Arenes under Aerobic Conditions
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The direct hydroxylation of 2-arylpyridines and 2-arylbenzothiazoles via the merger of organic photoredox and metal catalysis is reported where 4CzIPN is used as the visible-light photocatalyst and Pd(OAc)2 as the metal catalyst. This method has been employed to synthesize organic molecules exhibiting excited-state intramolecular proton transfer properties for generating tunable luminescence responses.
- Shah, Sk. Sheriff,Paul, Amrita,Bera, Manoranjan,Venkatesh, Yarra,Singh, N. D. Pradeep
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supporting information
p. 5533 - 5536
(2018/09/21)
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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 0016; 0021
(2018/05/16)
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- New preparation method of 2-substituted benzothiazole compound
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The invention provides a new preparation method of a 2-substituted benzothiazole compound, relating to the field of organic synthesis chemistry. According to the new preparation method, in existence of catalyst, oxidant and additive, methylbenzene or a derivative thereof reacts with o-aminothiophenol through free radial reaction so as to prepare the 2-substituted benzothiazole compound in one step. The new method is an example but not limited and has the beneficial effects that methylbenzene or a derivative thereof and o-aminothiophenol construct a C-S bond and a C-N bond through the free radical method for the first time so as to generate the 2-substituted benzothiazole by coupling reaction in one step, and the new preparation method has advantages that the method is efficient, concise and environmentally friendly, raw materials are easy to obtain, and the product purity is high and the like, and the method has good application value and research prospects.
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Paragraph 0058; 0060
(2018/09/11)
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- Cascade C(sp3)-S Bond Cleavage and Imidoyl C-S Formation: Radical Cyclization of 2-Isocyanoaryl Thioethers toward 2-Substituted Benzothiazoles
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A cascade radical cyclization of 2-isocyanoaryl thioethers with H-phosphorus oxides, organoboronic acids, or alkyl radical precursors has been efficiently developed, providing a novel and highly efficient methodology to structurally diverse C2-substituted benzothiazole derivatives with broad functional group tolerance and good yields. This cascade radical process achieves the first cycloaddition of an imidoyl radical from isocyanide to sulfur atom, rending C(sp2)-S bond formation.
- Yang, Wen-Chao,Wei, Kai,Sun, Xue,Zhu, Jie,Wu, Lei
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p. 3144 - 3147
(2018/05/28)
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- Elemental Sulfur-Mediated Decarboxylative Redox Cyclization Reaction: Copper-Catalyzed Synthesis of 2-Substituted Benzothiazoles
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A S 8 -mediated directed decarboxylative redox-cyclization strategy for the synthesis of 2-substituted benzothiazoles from o -iodoanilines, arylacetic acids, and elemental sulfur catalyzed by cheap copper metal has been developed. This reaction is operationally simple, ligand-free, compatible with a wide range of functional groups, and provides the desired products in good to excellent yields. In addition, a gram-scale experiment was carried out to furnish PMX 610, an antitumor drug.
- Wang, Xin,Li, Xiaotong,Hu, Renhe,Yang, Zhao,Gu, Ren,Ding, Sai,Li, Pengyi,Han, Shiqing
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supporting information
p. 219 - 224
(2017/10/09)
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- Phosphine free Mn-complex catalysed dehydrogenative C-C and C-heteroatom bond formation: A sustainable approach to synthesize quinoxaline, pyrazine, benzothiazole and quinoline derivatives
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Herein the first sustainable synthesis of quinoxalines, pyrazines and benzothiazoles catalysed by a phosphine free Mn(i) complex via acceptorless dehydrogenative coupling (ADC) is reported. This method is also applied successfully to synthesize quinolines via the dehydrogenation (removal of H2) and condensation (removal of H2O) reaction between 2-aminobenzyl alcohols and secondary alcohols.
- Das, Kalicharan,Mondal, Avijit,Srimani, Dipankar
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supporting information
p. 10582 - 10585
(2018/09/25)
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- Deep eutectic solvent-catalyzed arylation of benzoxazoles with aromatic aldehydes
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A novel and efficient methodology for the arylation of benzoxazoles with aromatic aldehydes catalyzed by deep eutectic solvent has been developed. The reaction smoothly proceeded with a wide range of substrates to give the desired products in high yields within short reaction time. Deep eutectic solvents are easily recovered and reused without significant loss of catalytic activity.
- Tran, Phuong Hoang,Thi Hang, Anh-Hung
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p. 11127 - 11133
(2018/03/26)
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