cas 1629-07-8, 2-(3-FLUOROPHENYL)-1,3-BENZOTHIAZOLE

Articles about 1629-07-8Total 29 be found

Article title
Article abstract
Author
Journal number and time
Download

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water
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
p. 14866 - 14882
(2021/10/25)

Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation
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
p. 2078 - 2083
(2021/04/05)

Method for preparing benzothiazole compound from visible light promoted N-(2-bromophenyl) thioamide
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.
-
Paragraph 0088-0090

(2021/06/22)

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions
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
supporting information
p. 4843 - 4848
(2021/06/28)

Photoinduced Heterogeneous C?H Arylation by a Reusable Hybrid Copper Catalyst
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
supporting information
p. 3509 - 3514
(2020/03/03)

Preparation method of 2-substituted benzothiazole
The invention discloses a preparation method of 2-substituted benzothiazole, and belongs to the field of organic chemical synthesis. The preparation method of the 2-substituted benzothiazole specifically comprises the following steps: by taking an N-aryl thioamide compound as a raw material and taking graphite-phase carbon nitride (g-C3N4) prepared by urea thermal polymerization condensation as aphotocatalyst, carrying out a cyclization reaction under a mild condition to prepare the 2-substituted benzothiazole. The method has the advantages of simple operation, cheap and easily available catalyst, mild reaction conditions, wide substrate application range, no strong oxidant and no metal residue, and provides an economical, practical, green and environment-friendly new method for synthesisof 2-substituted benzothiazole widely applied to the fields of medicines, dyes, pesticides and the like.
-
Paragraph 0100-0105

(2020/11/09)

Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions
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
p. 14254 - 14261
(2020/04/23)

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer
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
supporting information
p. 237 - 241
(2019/01/10)

Method for synthesizing benzothiazole by microwave radiation of benzothioamide compound in aqueous phase
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.
-
Paragraph 0013; 0052

(2019/02/13)

Method used for rapid preparation of benzo-heterocycle compound with physical grinding under solvent-free room temperature conditions
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.
-
Paragraph 0062; 0146

(2019/01/21)

New preparation method of 2-substituted benzothiazole compound
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.
-
Paragraph 0090; 0092

(2018/09/11)

Elemental Sulfur-Mediated Decarboxylative Redox Cyclization Reaction: Copper-Catalyzed Synthesis of 2-Substituted Benzothiazoles
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
supporting information
p. 219 - 224
(2017/10/09)

Method for preparing benzothiazole compound through microwave catalysis in water phase
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.
-
Paragraph 0037

(2018/05/16)

Elemental sulfur mediated cyclization via redox strategy: Synthesis of benzothiazoles from o-chloronitrobenzenes and benzyl chlorides
A novel metal-free synthesis of 2-substituted benzothiazoles from easily available o-chloronitrobenzenes and benzyl chlorides using elemental sulfur as traceless oxidizing agent has been developed. The protocol provides a simple, efficient, and atom-economic way to access to benzothiazoles in moderate to excellent yields. And the approach exhibited good functional group tolerance.
Wang, Xin,Miao, Dazhuang,Li, Xiaotong,Hu, Renhe,Yang, Zhao,Gu, Ren,Han, Shiqing
supporting information
p. 5194 - 5199
(2017/07/28)

One-pot copper-catalyzed synthesis of 2-substituted benzothiazoles from 2-iodoanilines, benzyl chlorides and elemental sulfur
An efficient one-pot three-component reaction of 2-iodoanilines, benzyl chlorides and elemental sulfur to form 2-substituted benzothiazoles in satisfactory yields (up to 98%) has been described. The reaction tolerated a wide range of functional groups on the aromatic ring. And heterocycle methylene chlorides substrates were also found to be compatible.
Yang, Zhao,Hu, Renhe,Li, Xiaotong,Wang, Xin,Gu, Ren,Han, Shiqing
supporting information
p. 2366 - 2369
(2017/05/29)

Photoinduced Copper-Catalyzed C-H Arylation at Room Temperature
Room-temperature azole C-H arylations were accomplished with inexpensive copper(I) compounds by means of photoinduced catalysis. The expedient copper catalysis set the stage for site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine. Copper light: Room-temperature C-H arylations of heteroarenes were accomplished with inexpensive copper compounds by photoinduced catalysis. The expedient copper catalysis leads to site-selective C-H arylations of non-aromatic oxazolines under mild reaction conditions, and provides step-economical access to the alkaloid natural products balsoxin and texamine.
Yang, Fanzhi,Koeller, Julian,Ackermann, Lutz
supporting information
p. 4759 - 4762
(2016/04/19)

Synthesis of 2-Arylbenzothiazoles by Copper-Catalyzed One-Pot Three-Component Reactions in Water
Copper-catalyzed three-component reactions of 2-iodoanilines, benzylamines, and sulfur powder are reported to afford benzothiazoles in a simple one-pot procedure by using water as solvent. A variety of 2-arylbenzothiazoles were obtained in moderate to good yields up to 88%.
Xu, Hualong,Luo, Chun,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
supporting information
p. 1207 - 1213
(2016/07/29)

S8-Mediated Cyclization of 2-Aminophenols/thiophenols with Arylmethyl Chloride: Approach to Benzoxazoles and Benzothiazoles
A metal-free approach to benzazoles from arylmethyl chlorides and 2-mercaptan/2-hydroxyanilines using elemental sulfur as a traceless oxidizing agent has been developed. The reactions proceeded in good to excellent yields, exhibiting good functional groups tolerance and gram-scale ability. A key mechanistic investigation indicated that the key intermediate trisulfide 6, which was characterized by NMR, HRMS and crystal X-ray crystallography, was separated in the reaction prior to the formation of the product.
Gan, Haifeng,Miao, Dazhuang,Pan, Qiang,Hu, Renhe,Li, Xiaotong,Han, Shiqing
supporting information
p. 1770 - 1774
(2016/07/07)

Catalyst-Free Synthesis of 2-Arylbenzothiazoles in an Air/DMSO Oxidant System
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
supporting information
p. 1387 - 1390
(2016/05/24)

Phenyliodonium diacetate mediated arylation of benzothiazoles with substituted styrenes
A metal-free synthesis of 2-arylbenzothiazoles was achieved using phenyliodonium diacetate (PIDA) from benzothiazoles and styrenes or β-nitrostyrenes. This transformation tolerates various functional groups such as methoxy, hydroxy, fluoro, chloro, and nitro groups.
Kamal, Ahmed,Reddy, N.V. Subba,Prasad
supporting information
p. 3972 - 3975
(2014/07/08)

Direct preparation of 2-benzothiazolylzinc bromide and its applications: A facile synthetic route to the preparation of 2-substituted benzothiazole derivatives
-
Park, Soo-Youl,Lee, Kyuhyuk,Kim, Seung-Hoi
p. 1848 - 1850
(2014/07/07)

A simple approach to benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine under solvent-free and catalyst-free conditions
A novel solvent-free and catalyst-free synthesis of benzothiazoles from 2-chloronitrobenzene, elemental sulfur, and aliphatic amine has been developed. The reaction tolerated a wide range of functionalities, and various benzothiazoles were synthesized in moderate to good yields in the absence of external oxidant or reductant.
Tong, Yao,Pan, Qiang,Jiang, Zengqiang,Miao, Dazhuang,Shi, Xuesong,Han, Shiqing
supporting information
p. 5499 - 5503
(2014/12/11)

Synthesis of benzothiazoles through copper-catalyzed one-pot three-component reactions with use of sodium hydrosulfide as a sulfur surrogate
Copper-catalyzed one-pot three-component reactions of 2-iodoanilines, aldehydes, and NaSH·n H2O afford benzothiazoles in good yields. When CuCl was employed as a catalyst in the absence of a ligand, a variety of aromatic aldehydes and substituted 2-iodoanilines reacted with NaSH·n H2O to produce the corresponding 2-arylbenzothiazoles in 70-98 % yields. The copper catalyst plays a key role in C-S bond formation between NaSH·n H2O and the aryl iodide that was formed from the condensation of 2-iodoaniline and aldehyde. It was found that NaSH·n H2O functions as a sulfur surrogate and oxidant in the formation of benzothiazole. 2-Iodoanilines, aldehydes, and NaSH·n H2O afford benzothiazoles in a one-pot reaction in the presence of a copper catalyst. The desired products can be obtainedin moderate to good yields. The copper catalyst plays a key role in C-S bond formation between aryl iodides and NaSH·n H2O. Copyright
Park, Namjin,Heo, Yumi,Kumar, Manian Rajesh,Kim, Yong,Song, Kwang Ho,Lee, Sunwoo
experimental part
p. 1984 - 1993
(2012/05/05)

Palladium(0) nanoparticles-catalyzed ligand-free direct arylation of benzothiazole via C-H bond functionalization
Palladium nanoparticles, generated in situ efficiently catalyzes direct 2-C-H arylation of benzothiazole without requirement of any ligand. A wide range of substituted aryl and heteroaryl iodides participate in this reaction producing a series of 2-aryl/heteroaryl-benzothiazoles in high yields.
Saha, Debasree,Adak, Laksmikanta,Ranu, Brindaban C.
experimental part
p. 5624 - 5627
(2010/11/03)

Rapid and convenient thermal or microwave-assisted synthesis of substituted 2-phenylbenzothiazoles
A simple one-step method for the synthesis of biologically relevant 2-phenylbenzothiazoles has been developed, using sodium metabisulfite as an oxidant following condensation between 2-aminothiophenol and substituted benzaldehydes. Attractive features of
Weekes, Ashley A.,Dix, Matthew C.,Bagley, Mark C.,Westwell, Andrew D.
experimental part
p. 3027 - 3032
(2010/11/05)

PTSA catalyzed simple and green synthesis of benzothiazole derivatives in water
p-Toluenesulfonic acid (10 mol%) was found to be an effective and efficient catalyst for the synthesis of 2-substituted benzothiazoles from aromatic aldehydes and 2-aminothiophenol in moderate to excellent yields in water. This method provides a simple an
Azizi, Najmedin,Amiri, Alireza Khajeh,Baghi, Roya,Bolourtchian, Mohammad,Hashemi, Mohammad M.
experimental part
p. 1471 - 1473
(2010/06/19)

A basis for reduced chemical library inhibition of firefly luciferase obtained from directed evolution
We measured the "draggability" of the ATP-dependent luciferase derived from the firefly Photuris pennsylvanica that was optimized using directed evolution (Ultra-Glo, Promega). Quantitative high-throughput screening (qHTS) was used to determine IC50
Auld, Douglas S.,Zhang, Ya-Qin,Southall, Noel T.,Rai, Ganesha,Landsman, Marc,MacLure, Jennifer,Langevin, Daniel,Thomas, Craig J.,Austin, Christopher P.,Inglese, James
supporting information; experimental part
p. 1450 - 1458
(2009/12/26)

A SYNTHESIS OF 2-SUBSTITUTED PHENYLBENZOTHIAZOLES
A one-pot synthesis of 2-substituted phenylbenzothiazoles is achieved when 2-aminobenzenethiol is treated with an excess of sodium hydride and aromatic nitriles in THF.This method allows to obtain substituted products (F, CF3, Cl or OCH3) in each ortho, m
Mettey, Yvette,Michaud, Sabine,Vierfond, Jean Michel
p. 1001 - 1006
(2007/10/02)

1-Methyl-2-pyrrolidinone: A Well-Adapted Solvent in the Benzothiazoles Synthesis
We describe the synthesis of a series of 2-aryl and 2-alkyl benzothiazoles with high yields using 1-methyl-2-pyrrolidinone as reaction solvent.
Brembilla, A.,Roizard, D.,Lochon, P.
p. 3379 - 3384
(2007/10/02)