65490-81-5Relevant academic research and scientific papers
Iron-Promoted Three-Component 2-Substituted Benzothiazole Formation via Nitroarene ortho-C-H Sulfuration with Elemental Sulfur
Xing, Qiaoyan,Ma, Yanfeng,Xie, Hao,Xiao, Fuhong,Zhang, Feng,Deng, Guo-Jun
, p. 1238 - 1246 (2019/01/21)
A three-component procedure for the preparation of 2-substituted benzothiazoles from nitroarenes, alcohols, and sulfur powder is described. The reaction showed a good functional group tolerance to provide the heterocyclic products in moderate to good yields. The sequential assembly involving nitro reduction, C-N condensation, and C-S bond formation has been realized in one pot.
Efficient 2-aryl benzothiazole formation from acetophenones, anilines, and elemental sulfur by iodine-catalyzed oxidative C(CO)-C(alkyl) bond cleavage
Liu, Yafeng,Yuan, Xinglong,Guo, Xin,Zhang, Xueguo,Chen, Baohua
, p. 6057 - 6062 (2018/09/11)
A novel and efficient iodine-catalyzed one-pot reaction of aromatic amines, acetophenones, and elemental sulfur for the synthesis of 2-aryl benzothiazoles is described. The process involves sequential C?S and C-N bond formation followed by C(CO)?C bond cleavage from readily accessible starting materials. A wide range of functional groups is tolerated under oxidant and metal-free condition and moderate to good product yields are obtained.
Room-temperature ligand-free Pd/C-catalyzed C-S bond formation: Synthesis of 2-substituted benzothiazoles
Cheng, Yannan,Peng, Qian,Fan, Weigang,Li, Pixu
, p. 5812 - 5819 (2014/07/08)
The synthesis of 2-substituted benzothiazoles has been achieved via cyclization of o-iodothiobenzanilide derivatives using Pd/C as the catalyst at room temperature. The protocol is ligand-free, additive-free, and high-yielding and involves very mild conditions.
Synthesis of 2-aryl benzothiazoles via K2S2O 8-mediated oxidative condensation of benzothiazoles with benzylamines
Yang, Zhiyong,Wang, Anwei,Chen, Xiang,Gui, Qingwen,Liu, Jidan,Tan, Ze,Wang, Hua,Shi, Ji-Cheng
supporting information, p. 1549 - 1554 (2013/08/23)
A novel way to synthesize 2-arylbenzothiazoles is described. Reactions of benzothiazoles with diverse benzylamines in the presence of K2S 2O8 and KOt-Bu in DMSO-H2O afforded the desired 2-arylbenzothiazoles in good yields. It is notable that no transition-metal catalyst is needed in this reaction. Compared with other known methods, this method of synthesizing 2-arylbenzothiazoles can be advantageous in cases where substituted benzothiazoles and benzylamines are readily available. Georg Thieme Verlag Stuttgart. New York.
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 (2007/10/02)
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.
