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.).
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..
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.
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.
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.
Copper-catalyzed multicomponent reactions of 2-iodoanilines, benzylamines, and elemental sulfur toward 2-arylbenzothiazoles
Wang, Rui,Ding, Yong-Liang,Liu, Hong,Peng, Shu,Ren, Jie,Li, Lei
, p. 945 - 949 (2014)
A relatively cheap copper salt-catalyzed, three-component approach providing 2-arylbenzothiazoles in good to excellent yields from readily available 2-iodoanilines, benzylamines, and sulfur powder is reported. This methodology allows preparation of various classes of 2-arylbenzothiazoles and provides a general, reliable approach.
A Facile One-Step Synthesis of 2-Arylbenzothiazoles
Osuka, Atsuhiro,Uno, Yukari,Horiuchi, Hiroharu,Suzuki, Hitomi
, p. 145 - 146 (1984)
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Synthesis of 2-Arylbenzothiazoles from Nitrobenzenes, Benzylamines, and Elemental Sulfur via Redox Cyclization
Imoto, Mitsutaka,Mizuno, Takumi,Nomoto, Akihiro,Ogawa, Akiya,Takeda, Motonori,Teramoto, Masahiro
supporting information, p. 386 - 390 (2022/03/02)
A sustainable advanced synthetic method was developed based on redox cyclization for the synthesis of 2-arylbenzothiazoles in good to excellent yields from readily available nitrobenzenes, benzylamines, and elemental sulfur without the use of transition-metal catalysts. This method is remarkable: nitro group reduction, a benzylamine redox reaction, sulfuration, condensation, and cyclization, all proceed in a single step to generate a heterocycle. It is also highly atom-economical and does not require any external oxidizing or reducing agents.
Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions
Bai, Jin,Yan, Sijia,Zhang, Zhuxia,Guo, Zhen,Zhou, Cong-Ying
, p. 4843 - 4848 (2021/06/28)
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.
