- 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)
-
- Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds
-
A photoelectrochemical strategy for the cross-dehydrogenative coupling of unactivated aliphatic hydrogen donors (e.g.alkanes) with benzothiazoles is reported. We used tetrabutylammonium decatungstate as the photocatalyst to activate strong C(sp3)-H bonds in the chosen substrates, while electrochemistry scavenged the extra electrons.
- Capaldo, Luca,Quadri, Lorenzo L.,Merli, Daniele,Ravelli, Davide
-
supporting information
p. 4424 - 4427
(2021/05/10)
-
- 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 0039-0041
(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; 0092
(2019/02/13)
-
- Heterogeneous copper-catalyzed synthesis of S-arylated 2-aminothiophenols via ring opening of benzothiazoles and C-S coupling using aryl halides
-
Chelate resins, which are polystyrene-divinylbenezene-based polymers bearing iminodiacetic acids or polyamines as ligands, supported copper catalysts (Cu/CR11 or Cu/CR20) in effectively catalyzing the ring cleaving S-arylation of benzothiazole with aryl i
- Ichikawa, Tomohiro,Matsuo, Tomohiro,Tachikawa, Takumu,Sawama, Yoshinari,Monguchi, Yasunari,Sajiki, Hironao
-
p. 793 - 805
(2019/04/26)
-
- 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)
-
- HEMOGLOBIN MODIFIER COMPOUNDS AND USES THEREOF
-
Described herein are compounds, including pharmaceutically acceptable salts thereof, methods of making such compounds, pharmaceutical compositions comprising such compounds, and methods of using such compounds to treat, prevent or diagnose blood-based diseases, disorders or conditions.
- -
-
Paragraph 00453
(2018/02/28)
-
- Thermolysis and radiofluorination of diaryliodonium salts derived from anilines
-
Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.
- Linstad, Ethan J.,Vāvere, Amy L.,Hu, Bao,Kempinger, Jayson J.,Snyder, Scott E.,DiMagno, Stephen G.
-
supporting information
p. 2246 - 2252
(2017/03/17)
-
- 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)
-
- 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)
-
- 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)
-
- 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)
-
- 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)
-
- Cu-catalyzed cross-dehydrogenative coupling reactions of (benzo)thiazoles with cyclic ethers
-
Copper-catalyzed cross-dehydrogenative coupling (CDC) reactions of (benzo)thiazoles with cyclic ethers were developed under mild conditions. In particular, the formation of C-C bonds via the CDC reactions between non-benzo-fused azoles and ethers are reported for the first time. In addition, the acetals, known as the masked 2-thiazolecarboxaldehydes, could be successfully obtained by this CDC reaction. The preliminary mechanism and supportive DFT calculations are discussed as well.
- Xie, Zengyang,Cai, Yuping,Hu, Hongwen,Lin, Chen,Jiang, Juli,Chen, Zhaoxu,Wang, Leyong,Pan, Yi
-
supporting information
p. 4600 - 4603
(2013/09/24)
-
- Mechanistic exploration of the palladium-catalyzed process for the synthesis of benzoxazoles and benzothiazoles
-
A convenient one-pot palladium-catalyzed cascade process for the preparation of both benzoxazoles and benzothiazoles has been developed. While these reactions proceed to give similar compounds the mechanisms governing the processes are different as are the experimental conditions employed.
- Bochatay, Valentin N.,Boissarie, Patrick J.,Murphy, John A.,Suckling, Colin J.,Lang, Stuart
-
p. 1471 - 1477
(2013/03/28)
-
- Optimization of hydroxybenzothiazoles as novel potent and selective inhibitors of 17β-HSD1
-
17β-HSD1 is a novel target for the treatment of estrogen-dependent diseases, as it catalyzes intracellular estradiol formation. Starting from two recently described compounds, highly active and selective inhibitors were developed. Benzoyl 6 and benzamide 17 are the most selective compounds toward 17β-HSD2 described so far. They also showed a promising profile regarding activity in T47-D cells, selectivity toward ERα and ERβ, inhibition of hepatic CYP enzymes, metabolic stability, and inhibition of marmoset 17β-HSD1 and 17β-HSD2.
- Spadaro, Alessandro,Frotscher, Martin,Hartmann, Rolf W.
-
scheme or table
p. 2469 - 2473
(2012/05/20)
-
- TBHP-mediated oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom in an amide
-
The first example of molecular sieve-promoted TBHP-mediated direct oxidative thiolation of an sp3 C-H bond adjacent to a nitrogen atom with disulfides under metal-free conditions, which allows for preparation of numerous S,N-containing compounds, is presented. Moreover, diverse benzothiazoles and a fipronil analog can be synthesized through this strategy.
- Tang, Ri-Yuan,Xie, Ye-Xiang,Xie, Yi-Li,Xiang, Jian-Nan,Li, Jin-Heng
-
supporting information; experimental part
p. 12867 - 12869
(2012/02/03)
-
- Copper-catalyzed activation of disulfides as a key step in the synthesis of benzothiazole moieties
-
A convenient synthesis of substituted benzothiazoles has been accomplished by way of a copper catalyzed reaction of aromatic disulfide amines and aldehydes. The process, which involves copper catalyzed activation of disulfide functionality, proceeds in a
- Hyvl, Jakub,Srogl, Jiri
-
supporting information; experimental part
p. 2849 - 2851
(2010/07/18)
-
- Synthesis and evaluation of 2-pyridylbenzothiazole, 2-pyridylbenzoxazole and 2-pyridylbenzofuran derivatives as 11C-PET imaging agents for β-amyloid plaques
-
The syntheses and SAR of new series of β-amyloid binding agents are reported. The effort to optimize signal-to-background ratios for these ligands are described. Compounds 8, 21 and 30 displayed desirable lipophilicity and pharmacokinetic properties. Compounds 8 and 21 were evaluated with in vitro autoradiographic studies and in vivo in APP/PS1 transgenic mice. It is shown that it was possible to increase the signal-to-background ratios compared to PIB 1, as demonstrated by compounds 8 and 21.
- Swahn, Britt-Marie,Wensbo, David,Sandell, Johan,Sohn, Daniel,Slivo, Can,Pyring, David,Malmstr?m, Jonas,Arzel, Erwan,Vallin, Michaela,Bergh, Margareta,Jeppsson, Fredrik,Johnson, Allan E.,Juréus, Anders,Neelissen, Jan,Svensson, Samuel
-
scheme or table
p. 1976 - 1980
(2010/07/07)
-
- (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)
-
- ACETAMIDE COMPOUNDS AS FUNGICIDES
-
Compounds of the general formula (I); wherein the substituents are as defined in claim 1, are useful as fungicides.
- -
-
Page/Page column 78
(2010/11/08)
-
- N-ALKYNYL-2-HETEROARYLOXYALKYLAMIDES FOR USE AS FUNGICIDES
-
Compounds of the general formula (I) are useful as fungicides wherein Het is a 5- or 6- linked group of the formula (a) or (b), and the variables are as defined in the claims.
- -
-
-
- N-ALKYNYL-2- (SUBSTITUTED ARYLOXY) ALKYLTHIOAMIDE DERIVATIVES AS FUNGICIDES
-
Fungicidal compounds of the general formula (1), wherein Ar is a group of the formula (A), (B1), (B2) or (C), or Ar is a 5- or 6-linked group of the formula (D1) or (D2); and R1, R2, R3, R4, R5, n, A1, A2, A3, A4, A5, Ka, Kb, L, M, V, W, X,Y and Z have the definitions given in claim 1.
- -
-
-
- 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)
-
- Synthetic studies on pentacyclic aromatic alkaloids, kuanoniamine A, 11-hydroxyascididemin, and neocalliactine acetate
-
A pentacyclic aromatic alkaloid, kuanoniamine A (6) was synthesized in three steps from 6-methoxybenzothiazole-4,7-dione (8) and 2-aminoacetophenone (9). 11-Hydroxyascididemin (4) was prepared from 5,8-quinolinedione (13, 14) or 1,4-acridinedione (20). The structure of neocalliactine acetate, a derivative of calliactine, was determined to be 5 by total synthesis from 6-methoxy-5,8-quinolinedione (28) and 2-amino-5-methoxyacetophenone (29).
- Kitahara, Yoshiyasu,Nakahara, Shinsuke,Yonezawa, Takanobu,Nagatsu, Masanori,Shibano, Yoshikazu,Kubo, Akinori
-
p. 17029 - 17038
(2007/10/03)
-