32729-67-2Relevant academic research and scientific papers
Microwave-assisted controllable synthesis of 2-acylbenzothiazoles and bibenzo[b][1,4]thiazines from aryl methyl ketones and disulfanediyldianilines
Qi, Yuquan,Gu, Xiaoyu,Huang, Xianqiang,Shen, Guodong,Yang, Bingchuan,He, Qingpeng,Xue, Zechun,Du, Mengcheng,Shi, Lilong,Yu, Bing
supporting information, p. 3544 - 3547 (2021/07/02)
A condition-controlled strategy for selectively synthesis of 2-acylbenzothiazoles and bibenzo[b][1,4]thiazines from aryl methyl ketones and disulfanediyldianilines was realized using I2/DMSO or I2/MeCN systems, respectively. The desired products were synthesized in only 15 min with moderate to excellent yields (50%-90%) under microwave-assisted, metal-free conditions. The strategy provides a great advantage for selective synthetic applications in the efficient synthesis of benzothiazoles and bibenzothiazines heterocycle compounds.
C2 substituted 2H-benzothiazole aryl acylated derivative, and synthesis method and application thereof
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Paragraph 0049-0050, (2021/07/08)
The invention discloses a C2 substituted 2H-benzothiazole aryl acylated derivative, and a synthesis method and application thereof. The preparation method of the derivative comprises the following steps: mixing substituted 2H-benzothiazole and substituted methyl benzene, adding into a solvent, in the presence of an oxidizing agent Selectfluor and an additive trifluoroacetic acid, carrying out a heating and stirring reaction in the air atmosphere, performing TLC monitoring is conducted till the reaction is finished, and separating and purifying the obtained reaction liquid to obtain the target product C2 substituted 2H-benzothiazole aryl acylated derivative. The substituted methyl benzene used in the invention is low in price, easy to obtain and good in chemical stability, the method has the advantages of being high in atom economy, simple in catalytic system, free of transition metal catalysts, good in product yield, wide in substrate range and the like, and the prepared compound structure can be further optimized as an anti-tumor drug lead.
C2-arylacylation of 2H-benzothiazoles with methyl arenes via Selectfluor oxidation
Chen, Bo,Kong, Yao-Lei,Liu, Jin-Chuan,Lu, Qi,Sun, Xiao-Tong,Weng, Jian-Quan
supporting information, (2021/06/03)
An efficient Selectfluor-oxidative protocol was developed for the direct C2-arylacylation of 2H-benzothiazoles via the radical reaction of 2H-benzothiazoles with methyl arenes. Selectfluor can effectively promote the oxidative cross-coupling without an ex
New synthesis of 2-aroylbenzothiazolesviametal-free domino transformations of anilines, acetophenones, and elemental sulfur
Doan, Khang V.,Doan, Son H.,Huynh, Tien V.,Luong, Ngoc T. K.,Nguyen, Duyen T. P.,Nguyen, Tung T.,Phan, Nam T. S.
, p. 18423 - 18433 (2020/06/08)
A new synthesis of 2-aroylbenzothiazolesviaiodine-promoted domino transformations of anilines, acetophenones, and elemental sulfur was demonstrated. The highlights of this tandem synthesis are (1) easily available anilines and acetophenones as feedstock;
Iodine- And TBHP-Promoted Acylation of Benzothiazoles under Metal-Free Conditions
Wang, Bin,Zhang, Qianwei,Guo, Zhongqi,Ablajan, Keyume
, p. 3058 - 3064 (2020/08/28)
A simple protocol for the synthesis of 2-acylbenzothiazoles using aryl ketones and benzothiazoles in the presence of I 2and TBHP is described. Acylation of the benzothiazoles is achieved through a sequence involving oxidation of the aryl ketone to an aryl glyoxal, ring-opening of the benzothiazole followed by condensation of the amino group with the aryl glyoxal, cyclization and oxidation. The method avoids the use of metals and toxic solvents. In addition, this protocol has the advantage of broad scope and provides good to excellent product yields.
Method for simply and conveniently synthesizing heterocyclic aryl ketone compound
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Paragraph 0046; 0047; 0048; 0049; 0050; 0053, (2019/01/23)
The invention discloses a method for simply and conveniently synthesizing a heterocyclic aryl ketone compound, and belongs to the technical field of the organic chemistry. The method comprises the following steps: using a benzyl heterocyclic compound as a reaction raw material, in a polar solvent, heating and reacting in an oxygen atmosphere, to obtain a multi-substituted ketone compound. The method is capable of using molecular oxygen as an oxidizing agent, green and environmental, and capable of preparing ketone by directly promoting selective oxidation and functionalization of a Csp3-H bond, and broadening a synthetic method for the ketone compound.
Ball-milling synthesized hydrotalcite supported Cu-Mn mixed oxide under solvent-free conditions: An active catalyst for aerobic oxidative synthesis of 2-acylbenzothiazoles and quinoxalines
Meng, Xu,Bi, Xiuru,Yu, Chaoying,Chen, Gexin,Chen, Baohua,Jing, Zhenqiang,Zhao, Peiqing
supporting information, p. 4638 - 4644 (2018/10/23)
A rapid solvent-free ball-milling method was developed to prepare a hydrophobic hydrotalcite supported Cu-Mn mixed oxide catalyst (Cu-Mn/HT). The mechanochemically prepared catalyst exhibited high catalytic activity and recyclability towards the aerobic synthesis of 2-acylbenzothiazoles and quinoxalines in green medium ethanol compared with the ones synthesized via grinding and wet-impregnation. Moreover, control experiments showed that the catalyst was successfully used in green oxidative esterification and coupling as well. Cu-Mn/HT was characterized by BET, ICP, XRD, XPS, SEM and TEM, which indicated that more surface oxygen vacancies and formed CuMn2O4 species on HT might contribute to the catalytic activity.
Elemental sulfur mediated 2-substituted benzothiazole formation from 2-aminobenzenethiols and arylacetylenes or styrenes under metal-free conditions
Li, Guozheng,Jiang, Jingjing,Zhang, Feng,Xiao, Fuhong,Deng, Guo-Jun
supporting information, p. 10024 - 10028 (2017/12/26)
An oxidative cyclization of 2-aminothiophenols and arylacetylenes or styrenes for the synthesis of 2-alkylbenzothiazoles and 2-acylbenzothiazoles has been developed. Elemental sulfur was used as the effective oxidant to give the corresponding product in g
Concise Access to 2-Aroylbenzothiazoles by Redox Condensation Reaction between o-Halonitrobenzenes, Acetophenones, and Elemental Sulfur
Nguyen, Thanh Binh,Pasturaud, Karine,Ermolenko, Ludmila,Al-Mourabit, Ali
supporting information, p. 2562 - 2565 (2015/06/02)
A wide range of 2-aroylbenzothiazoles 3 including some pharmacologically relevant derivatives can be obtained in high yields by simply heating o-halonitrobenzenes 1, acetophenones 2, elemental sulfur, and N-methylmorpholine. This three-component nitro methyl coupling was found to occur in an excellent atom-, step-, and redox-efficient manner in which elemental sulfur played the role of nucleophile building block and redox moderating agent to fulfill electronic requirements of the global reaction. (Chemical Equation Presented).
Chemoselective copper-catalyzed acylation of benzothiazoles with aryl methyl ketones
Feng, Qiang,Song, Qiuling
supporting information, p. 2445 - 2452 (2014/10/15)
A copper(I) iodide-catalyzed, highly efficient acylation of benzothiazoles with aryl methyl ketones as carbonyl sources under a nitrogen atmosphere was developed. This is an unprecedented protocol and an extremely efficient method for the selective synthesis of 2-acylbenzothiazoles from commercially available, cheap starting materials with excellent chemoselectivity, good functional group tolerability and high turnover numbers (up to 14,200); also scaling up to 160mmol without loss of the efficiency is possible. A variety of 2-acylbenzothiazoles was smoothly prepared in good to excellent yields from aryl methyl ketones and benzothiazoles by a one-pot domino protocol of combined sp3 C-H oxidation, ring opening, and condensation.
