65490-80-4Relevant academic research and scientific papers
Metal-Free Synthesis of 2-Arylbenzothiazoles from Aldehydes, Amines, and Thiocyanate
Dey, Amrita,Hajra, Alakananda
supporting information, p. 1686 - 1689 (2019/03/11)
A highly efficient method for the synthesis of 2-arylbenzothiazoles has been developed using readily available aromatic amines, benzaldehydes, and NH4SCN as a sulfur source. A library of 2-arylbenzothiazoles with wide functional group compatibility has been synthesized in good yields through iodine-mediated oxidative annulation.
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.
Development of (quinolinyl)amido-based pincer palladium complexes: A robust and phosphine-free catalyst system for C-H arylation of benzothiazoles
Pandiri, Hanumanprasad,Soni, Vineeta,Gonnade, Rajesh G.,Punji, Benudhar
, p. 3543 - 3554 (2017/07/12)
(Quinolinyl)amido-ligated palladium(ii) complexes have been synthesized and applied in the catalytic C-H bond arylation of benzothiazoles. The tridentate ligand precursors R2N-C(O)CH2-(NH)-C9H6N [(R2NNN8-Q)-H; R2N = morpholinyl, Me-N-piperazinyl] and the pincer palladium complexes [κN,κN,κN-{R2N-C(O)CH2-(μ-N)-C9H6N}]PdX [(R2NNN8-Q)PdX {R2N = Et2N, morpholinyl, Me-N-piperazinyl; X = OAc or Cl}] were efficiently synthesized, and characterized by various analytical techniques. The iodo derivative (Et2NNN8-Q)PdI was obtained in excellent yield by the treatment of the complex (Et2NNN8-Q)PdCl with KI. The molecular structures of complexes (Et2NNN8-Q)Pd(OAc) (2a), (Et2NNN8-Q)PdCl (3a) and (Et2NNN8-Q)PdI (4a) were elucidated by X-ray crystallography. Complex 3a was found to be the most efficient catalyst for direct C-H bond arylation of substituted benzothiazoles with diverse aryl iodides using a mild base, K2CO3. The working catalyst system 3a is highly robust and can be recycled and reused several times for the arylation of benzothiazole without loss of catalytic activity. Preliminary mechanistic investigations using controlled studies and kinetic analysis have been performed, which greatly support a molecular mechanism for the arylation.
Copper-catalyzed solvent-free redox condensation of benzothiazoles with aldehydes or benzylic alcohols
Zhang, Mingliang,Lu, Wen-Ting,Ruan, Wenqing,Zhang, Hui-Jun,Wen, Ting-Bin
, p. 1806 - 1809 (2014/03/21)
An efficient and practical method for the construction of 2-aryl-and 2-alkyl-substituted benzothiazoles via a copper-catalyzed redox condensation process between benzothiazoles and aldehydes or benzylic alcohols has been developed. The reaction proceeded under mild reaction conditions using environmentally benign tert-butyl hydroperoxide (TBHP) as the oxidant. A reaction mechanism involving the ring-opening of benzothiazoles initiated by the attack of acyl radical on the thiazole ring and intramolecular condensation is proposed based on the isolation of an anilide disulfide intermediate.
Synthesis of 2-substituted benzothiazoles from 1-iodo-2-nitrobenzenes by a copper-catalyzed one-pot three-component reaction
Liu, Jidan,Gui, Qingwen,Yang, Zhiyong,Tan, Ze,Guo, Ruqing,Shi, Ji-Cheng
, p. 943 - 951 (2013/05/08)
A novel method was developed for synthesizing 2-substituted 1,3-benzothiazoles through a copper-catalyzed, one-pot, three-component reaction of a 1-iodo-2-nitrobenzene with sodium sulfide and an aldehyde. Georg Thieme Verlag Stuttgart - New York.
