- Iodine-promoted ring-opening methylation of benzothiazoles with dimethyl sulfite
-
A halogen-bond promoted ring-opening methylation of benzothiazoles has been developed using dimethyl sulphite as a methylating reagent in the presence of a base. This approach represents a simple and efficient synthesis ofN-methyl-N-(o-methylthio)phenyl amides, and features direct construction of both N-Me and S-Me bonds in a one-pot reaction through the decomposition of easily prepared benzothiazoles.
- Guo, Ying-Qiong,Chen, Fan,Deng, Chen-Liang,Zhang, Xing-Guo
-
supporting information
p. 1923 - 1926
(2021/03/02)
-
- Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines
-
The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.
- Wu, Yue,Guo, Peng,Chen, Long,Duan, Weijie,Yang, Zengzhuan,Wang, Tao,Chen, Ting,Xiong, Fei
-
supporting information
p. 3271 - 3274
(2021/04/07)
-
- K2S as Sulfur Source and DMSO as Carbon Source for the Synthesis of 2-Unsubstituted Benzothiazoles
-
We describe a three-component reaction of o-iodoanilines with K2S and DMSO that provides 2-unsubstituted benzothiazoles in moderate to good isolated yields with good functional group tolerance. Electron-rich aromatic amines and o-phenylenediamines instead of o-iodoanilines provided 2-unsubstituted benzothiazoles and 2-unsubstituted benzimidazoles with and without K2S under similar conditions. Notably, DMSO plays three vital roles: carbon source, solvent, and oxidant.
- Deng, Guobo,Kuang, Daizhi,Liang, Yun,Yang, Yuan,Yu, Jiangxi,Zhang, Fuxing,Zhu, Xiaoming
-
supporting information
p. 3789 - 3793
(2020/06/04)
-
- Synthetic method of ammonium acetate-mediated benzothiazole compound
-
The invention discloses a synthetic method of an ammonium acetate-mediated benzothiazole compound . The synthetic method comprises the steps: adding an o-haloaniline derivative, potassium sulfide, dimethyl sulfoxide, a catalyst, an additive 1 and an additive 2 into a reaction tube, carrying out a stirring reaction at the temperature of 130-150 DEG C, cooling to room temperature after the reactionis finished, and separating and purifying the product to obtain the benzothiazole compound. The invention provides the synthetic method of the benzothiazole compound by taking K2S as a sulfur source,DMSO as a carbon source and an oxidizing agent, an o-haloaniline derivative as a substrate and an ammonium acetate mediated three-component one-pot method. The method has the advantages of fewer reaction steps, mild reaction conditions, good functional group tolerance and the like.
- -
-
Paragraph 0036-0038
(2020/11/23)
-
- 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; 0077
(2019/02/13)
-
- N-Iodosuccinimide involved one-pot metal-free synthesis of 2-heteroaromatic benzothiazole compounds
-
A one-pot protocol for the synthesis of structurally diverse 2-hetarylbenzothiazoles via oxidative condensation of the sp3 C-H bond with benzothiazoles has been described. This process is metal free and operationally simple. A series of 2-hetarylbenzothiazoles were prepared in moderate to good yield under mild conditions.
- Chu, Xianglong,Duan, Tiantian,Liu, Xuan,Feng, Lei,Jia, Jiong,Ma, Chen
-
supporting information
p. 1606 - 1611
(2017/02/23)
-
- Synthesis of benzothiazoles from 2-aminobenzenethiols in the presence of a reusable polythiazolium precatalyst under atmospheric pressure of carbon dioxide
-
Synthesis of benzothiazoles from 2-aminobenzenethiols and carbon dioxide was carried out using poly(3,4-dimethyl-5-vinylthiazolium) iodide as a precatalyst to in situ generation of NHCs by deprotonation. The reaction was successfully carried out under mild conditions (1 atm of CO2 and 60–70 °C) with a broad substrate scope and functional group tolerance. The precatalyst salt was recovered and reused for several times without any loss of activity.
- Chun, Supill,Yang, Sabyuk,Chung, Young Keun
-
p. 3438 - 3442
(2017/05/31)
-
- Atmospheric CO2 promoted synthesis of N-containing heterocycles over B(C6F5)3 catalyst
-
B(C6F5)3 combined with atmospheric CO2 was found to be highly effective for the cyclization of ortho-substituted aniline derivatives with N,N-dimethylformamide (DMF), and a series of N-containing heterocycles including benzothiazoles, benzimidazoles, quinazolinone and benzoxazole were obtained in good to excellent yields.
- Gao, Xiang,Yu, Bo,Mei, Qingqing,Yang, Zhenzhen,Zhao, Yanfei,Zhang, Hongye,Hao, Leiduan,Liu, Zhimin
-
p. 8282 - 8287
(2016/10/11)
-
- Ionic Liquid-Catalyzed C-S Bond Construction using CO2 as a C1 Building Block under Mild Conditions: A Metal-Free Route to Synthesis of Benzothiazoles
-
The construction of the C-S bond using CO2 as a C1 feedstock can be considered as a green route for the synthesis of S-containing compounds and is of great significance. Herein, we report the acetate-based ionic liquids (ILs)-catalyzed synthesis of benzothiazoles via cyclization of 2-aminothiophenols with CO2 and hydrosilane under mild conditions (e.g., 60 °C, 0.5 MPa). It was found that the IL (e.g., 1-butyl-3-methylimidazolium acetate, [Bmim][OAc]) served as a multifunctional catalyst with activating CO2 and hydrosilane to form a formoxysilane intermediate, as well as simultaneously activating 2-aminothiophenols through a hydrogen bond, finally resulting in the production of benzothiazoles. [Bmim][OAc] showed the best performance, and a series of benzothiazoles were obtained in high yields. To the best of our knowledge, this is the first protocol for the synthesis of benzothiazoles using CO2 as a C1 building block under metal-free and mild conditions.
- Gao, Xiang,Yu, Bo,Yang, Zhenzhen,Zhao, Yanfei,Zhang, Hongye,Hao, Leiduan,Han, Buxing,Liu, Zhimin
-
p. 6648 - 6652
(2015/11/23)
-
- Iron-catalyzed arylation or aroylation of benzothiazoles with benzylic alcohols and aryl ketones
-
An iron-catalyzed arylation or aroylation of benzothiazoles with alcohols and aryl ketones via an in situ cross-trapping strategy has been described. Both the use of an iron catalyst and the ratio of substrates are important for this transformation, and this reaction is sensitive to the electronic effects of the substituents.
- Wang, Jian,Zhang, Xiao-Zhuan,Chen, Shan-Yong,Yu, Xiao-Qi
-
supporting information
p. 245 - 250
(2014/01/06)
-
- Hydrosilane-promoted cyclization of 2-aminothiophenols by CO2to benzothiazoles
-
A new route is presented to synthesize benzothiazoles via cyclization of 2-aminothiophenols by CO2 in the presence of diethylsilane catalyzed by 1,5-diazabicyclo[4.3.0]non-5-ene, and a series of benzothiazoles were obtained in good yields.
- Gao, Xiang,Yu, Bo,Zhao, Yanfei,Hao, Leiduan,Liu, Zhimin
-
p. 56957 - 56960
(2015/01/08)
-
- Dual C-H activations of electron-deficient heteroarenes: Palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides
-
The palladium-catalyzed, copper-promoted cross-dehydrogenative-coupling (CDC) of electron-deficient thiazoles with azine N-oxides through dual C-H activations was developed. It was found that copper(II) pivalate was an efficient dual-function reagent for the oxidative cross-coupling reactions, playing the roles of both an oxidant and a C-H bond activation promoter. This methodology provides a simple way to construct 2-thiazolyl pyridine moiety.
- Fu, Xiao-Pu,Xuan, Qing-Qing,Liu, Li,Wang, Dong,Chen, Yong-Jun,Li, Chao-Jun
-
p. 4436 - 4444
(2013/06/26)
-
- Palladium-catalyzed direct phosphonation of azoles with dialkyl phosphites
-
The first Pd-catalyzed direct phosphonation of azoles with dialkyl phosphites has been achieved without addition of base or acid. This method involves the oxidative cleavage of C-H and P(O)-H bonds and represents an atom-efficiency alternative to the classical phosphonation of Ar-X. A Pd II/PdIV mechanism has been studied and proposed.
- Hou, Chaodong,Ren, Yunlai,Lang, Rui,Hu, Xiaoxue,Xia, Chungu,Li, Fuwei
-
supporting information; experimental part
p. 5181 - 5183
(2012/06/01)
-
- Carbon dioxide as the C1 source for direct C-H functionalization of aromatic heterocycles
-
(Equation Presented). A simple and straightforward method has been developed for the direct carboxylation of aromatic heterocylces such as oxazoles, thiazoles, and oxadiazoles using CO2 as the C1 source. The reactions require no metal catalyst and only Cs2CO3 as the base. A good functional group tolerance is achieved.
- Vechorkin, Oleg,Hirt, Nathalie,Hu, Xile
-
supporting information; experimental part
p. 3567 - 3569
(2010/10/02)
-
- (3R)-3-Amino-4-(2,4,5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy)benzothiazol-2-yl]tetrahydropyran-4-yl}butanamide as a potent dipeptidyl peptidase IV inhibitor for the treatment of type 2 diabetes
-
Novel series of 3-amino-N-(4-aryl-1,1-dioxothian-4-yl)butanamides and 3-amino-N-(4-aryltetrahydropyran-4-yl)butanamides were synthesized and evaluated as dipeptidyl peptidase IV (DPP-IV) inhibitors. Derivatives incorporating the 6-substituted benzothiazole group showed highly potent DPP-IV inhibitory activity. Oral administration of (3R)-3-amino-4-(2,4,5-trifluorophenyl)-N-{4-[6-(2-methoxyethoxy)benzothiazol-2-yl]tetrahydropyran-4-yl}butanamide (12u) reduced blood glucose excursion in an oral glucose tolerance test.
- Nitta, Aiko,Fujii, Hideaki,Sakami, Satoshi,Nishimura, Yutaka,Ohyama, Tomofumi,Satoh, Mikiya,Nakaki, Junko,Satoh, Shiho,Inada, Chifumi,Kozono, Hideki,Kumagai, Hiroki,Shimamura, Masahiro,Fukazawa, Tominaga,Kawai, Hideki
-
scheme or table
p. 5435 - 5438
(2009/05/30)
-
- Syntheses of 2,4-diaryl-2,3-dihydro-1,5-benzothiazepines
-
The condensation of α,β-unsaturated ketones with substituted o-aminothiophenols, obtained by reductive cleavage of the corresponding disulfides in the presence of triphenylphosphine, is an effective method for the synthesis of 2,4-diaryl-2,3-dihydro-1,5-b
- Katritzky,Rogovoy,Chassaing,Vvedensky,Forood,Flatt,Nakai
-
p. 1655 - 1658
(2007/10/03)
-
- Deamination of 2-aminothiazoles and 3-amino-1,2,4-triazines with nitric oxide in the presence of a catalytic amount of oxygen
-
2-Aminothiazoles, 2-aminobenzazoles, and 3-amino-1,2,4-triazines were deaminated using nitric oxide (NO) in the presence of a catalytic amount of oxygen to afford corresponding unsubstituted heterocycles in good yields.
- Itoh, Takashi,Matsuya, Yuji,Nagata, Kazuhiro,Ohsawa, Akio
-
p. 1547 - 1549
(2007/10/03)
-
- Highly selective aldose reductase inhibitors. II. Optimization of the aryl part of 3-(arylmethyl)-2,4,5-trioxoimidazolidine-1-acetic acids
-
Accumulation of intracellular sorbitol, the product of glucose reduction catalyzed by aldose reductase (AR) [EC 1.1.1.21], is thought to be the main culprit in the development of diabetic complications. A series of 3- arylalkyl-2,4,5-trioxoimidazolidine-1-acetic acids was prepared and tested for inhibitory activities towards AR and aldehyde reductase (ALR) [EC 1.1.1.2]. These derivatives showed strong inhibitory activity against AR without markedly inhibiting ALR. In particular, the compounds with 3- nitrophenyl, 4-chloro-3-nitrophenyl, and chloro-substituted benzothiazolyl groups as the aryl part showed powerful AR-inhibitory activity. The chloro- substituted benzothiazolyl compound showed an AR selectivity of more than 5000 fold.
- Kotani, Takayuki,Ishii, Akira,Nagaki, Yasuhiro,Toyomaki, Yoshio,Yago, Hisashi,Suehiro, Seishi,Okukado, Nobuhisa,Okamoto, Kaoru
-
p. 297 - 304
(2007/10/03)
-