10205-58-0Relevant articles and documents
Synthesis of Benzothiazoles via Photooxidative Decarboxylation of α-Keto Acids
Monga, Aparna,Bagchi, Sourav,Soni, Raj Kumar,Sharma, Anuj
, p. 2232 - 2237 (2020)
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.).
Direct arylation of benzoazoles with aldehydes utilizing metal-organic framework Fe3O(BDC)3 as a recyclable heterogeneous catalyst
Doan, Son H.,Nguyen, Khoa D.,Nguyen, Tung T.,Phan, Nam T. S.
, p. 1423 - 1431 (2017)
A metal-organic framework Fe3O(BDC)3 was synthesized and used as a recyclable heterogeneous catalyst for the direct arylation of azoles with benzaldehydes. Following this protocol, inexpensive and commercially available benzaldehydes could act as an aryl source for the transformation, replacing the aryl halides normally employed in the conventional cross-coupling reactions. The catalyst disclosed higher catalytic productivity for the formation of aryl-substituted azoles than various MOFs and diverse homogeneous iron catalysts. The conversion was considerably regulated by the solvent and the oxidant, and the combination of N-methyl-2-pyrrolidone with di-tert-butyl peroxide offered the best yield. Heterogeneous catalysis was verified for the reaction, and the production of aryl-substituted azoles was only feasible in the presence of the iron framework. It was possible to reuse the catalyst for the direct arylation of azoles with aldehydes while its catalytic activity was preserved for multiple cycles. To our best judgment, this direct arylation of azoles with aldehydes utilizing solid catalysts has not been previously reported.
Copper-Catalyzed Arylation of Benzothiazoles with Toluene Derivatives: Synthesis of 2-Arylbenzothiazole
Li, Chengliang,Deng, Hongmei,Jin, Tao,Liu, Zhiqiang,Jiang, Ruolan,Li, Chunju,Jia, Xueshun,Li, Jian
, p. 4350 - 4356 (2017)
A copper-catalyzed reaction of benzothiazole and readily available toluene derivatives has been disclosed. This protocol is proposed to proceed through the oxidation of toluene and ring opening of benzothiazole, thus providing a new pathway for the synthesis of 2-arylbenzothiazoles..
Quaternary ammonium salt as alkylation agent in three-component reactions for the synthesis of benzothiazoles in water
Pan, Lei,Yu, Lintao,Wu, Zhiqing,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
, p. 27775 - 27779 (2014)
Substituted benzothiazoles are synthesized by metal-catalyst-free three-component reactions of o-iodoaniline, quaternary ammonium salt, and sulfur powder in water with moderate-to-excellent yields up to 95%. This journal is the Partner Organisations 2014.
Reactions of Aldonitrones with Phenylphosphonothioic Dichloride and Related Compounds. Formation of 2-Arylbenzothiazoles from α,N-Diarylnitrones
Yoshifuji, Masaaki,Nagase, Rihei,Kawashima, Takayuki,Inamoto, Naoki
, p. 870 - 872 (1982)
Reactions of α-aryl-N-methylnitrones with phenylphosphonothioic dichloride (1), diphenylphosphinothioic chloride (6), or thiophosphoryl trichloride (7) gave N-methylbenzamide and N-methylthiobenzamide derivatives, and the latter became major in the presence of tertiary amine. α,N-Diarylnitrones (4) reacted with 1 to give 2-arylbenzothiazoles (5) at room temperature in moderate yields.Reaction of 4 with 6 (at room temperature) or 7 (in refluxing THF) gave 5 in a low yield, whereas a similar reaction of 4 with 7 at 0 deg C afforded N-benzylidene-2-chloroaniline in a high yield.A mechanism for the formation of 5 has been discussed briefly.
Homoleptic tris-cyclometalated iridium complexes with 2-phenylbenzothiazole ligands for highly efficient orange OLEDs
Wang, Renjie,Liu, Di,Ren, Huicai,Zhang, Ting,Wang, Xinzeng,Li, Jiuyan
, p. 15494 - 15500 (2011)
Homoleptic tris-cyclometalated iridium(iii) complexes containing 2-phenylbenzothiazole derivatives as ligands have been successfully synthesized and characterized for the first time. Electron-donating (CH3, OCH3) and -withdrawing groups (F) were introduced into the 6-position of the benzothiazole moiety in the ligands to verify their influence on the optical and electronic properties of the complexes. Organic light-emitting diodes using these iridium complexes as doped emitters exhibited orange electrophosphorescence with excellent performances. An extremely high brightness of 95800 cd m-2 and a maximum luminance efficiency of 87.9 cd A -1 (46.0 lm W-1) were achieved for the pristine complex without any substituent in the ligand. These performances represent a significant improvement for vacuum-deposited orange OLEDs and the new record of the efficiencies for orange OLEDs reported so far. The substituents in the ligand were observed to be rather unimportant to influence the performance of this series of iridium complexes.
Iron-catalyzed arylation or aroylation of benzothiazoles with benzylic alcohols and aryl ketones
Wang, Jian,Zhang, Xiao-Zhuan,Chen, Shan-Yong,Yu, Xiao-Qi
, p. 245 - 250 (2014)
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.
Cu-catalyzed one-pot synthesis of unsymmetrical diaryl thioethers by coupling of aryl halides using a thiol precursor
Prasad,Sekar, Govindasamy
, p. 1008 - 1011 (2011)
An efficient Cu-catalyzed one-pot approach for the synthesis of unsymmetrical diaryl thioethers using potassium ethyl xanthogenate as a thiol surrogate is developed. This new protocol avoids usage of intricate thiols and makes use of its easily available xanthate as a precursor, and thiol will be generated in situ to prepare the diaryl thioethers through a Cu-catalyzed double arylation. This strategy was further successfully utilized for the synthesis of symmetrical diaryl thioethers, aryl alkyl thioethers, and benzothiazoles. (Figure Presented)
Elemental sulfur mediated decarboxylative redox cyclization reaction of o -chloronitroarenes and arylacetic acids
Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
, p. 976 - 978 (2015)
A decarboxylative redox cyclization strategy has been developed for the synthesis of 2-substituted benzothiazoles by the reaction of o-chloronitroarenes and arylacetic acids in the presence of elemental sulfur/N-methylmorpholine under metal- and solvent-free conditions.
Visible-Light-Driven Photocatalyst- and Additive-Free Cross-Coupling of β-Ketothioamides with α-Diazo 1,3-Diketones: Access to Highly Functionalized Thiazolines
Ansari, Monish Arbaz,Yadav, Dhananjay,Singh, Maya Shankar
, p. 8083 - 8089 (2020)
A photocatalyst- and additive-free, visible-light-mediated chemoselective domino protocol was devised to access fully substituted thiazoline derivatives from β-ketothioamides and α-diazo 1,3-diketones at moderate temperature in open air. The reaction proc
