445298-04-4Relevant academic research and scientific papers
Oxidant/Solvent-Controlled I2-Catalyzed Domino Annulation for Selective Synthesis of 2-Aroylbenzothiazoles and 2-Arylbenzothiazoles under Metal-Free Conditions
Ma, Renchao,Ding, Yuxin,Chen, Rener,Wang, Zhiming,Wang, Lei,Ma, Yongmin
, p. 310 - 321 (2021/01/09)
A simple and practical domino protocol for the selective synthesis of 2-aroylbenzothiazoles and 2-aryl benzothiazoles catalyzed by I2 is developed under metal-free conditions. The reaction outcomes are exclusively controlled by the reaction oxidant/medium. With DMSO employed as both the solvent and the oxidant, an oxidation of aromatic methyl ketones takes precedence over the condensation with 2-aminobenzenethiols. On the other hand, when the reaction was carried out in PhNO2 or in 1,4-dioxane containing PhNO2, the condensation of aromatic methyl ketones with 2-aminobenzenethiols has priority to form imines which is followed by an oxidation of the methyl group from ketones to afford 2-arylbenzothiazoles as a sole product. The PhNO2/I2 co-catalytic system is proposed first time.
Chemoselective copper-catalyzed acylation of benzothiazoles with aryl methyl ketones
Feng, Qiang,Song, Qiuling
supporting information, p. 2445 - 2452 (2014/10/15)
A copper(I) iodide-catalyzed, highly efficient acylation of benzothiazoles with aryl methyl ketones as carbonyl sources under a nitrogen atmosphere was developed. This is an unprecedented protocol and an extremely efficient method for the selective synthesis of 2-acylbenzothiazoles from commercially available, cheap starting materials with excellent chemoselectivity, good functional group tolerability and high turnover numbers (up to 14,200); also scaling up to 160mmol without loss of the efficiency is possible. A variety of 2-acylbenzothiazoles was smoothly prepared in good to excellent yields from aryl methyl ketones and benzothiazoles by a one-pot domino protocol of combined sp3 C-H oxidation, ring opening, and condensation.
Synthesis of 2-Acylbenzothiazoles via the Cu(OTf)2-Catalyzed tandem reaction of β,β-Dihalidestyrenes with 2,2′- Disulfanediyldianilines
Zhou, Zeng-Le,Fang, Tao,Tang, Ri-Yuan,Zhang, Xing-Guo,Deng, Chen-Liang
supporting information, p. 255 - 260 (2014/02/14)
A new method has been developed for the one-pot construction of 2-acylbenzothiazoles via the Cu(OTf)2-catalyzed tandem reaction of β,β-dihalidestyrenes with 2,2′-disulfane-diyldianilines. A variety of different dihalidestyrenes and diphenyldisulfanes were efficiently converted into the corresponding 2-acylbenzothiszole derivatives in the presence of Cu(OTf)2. Most importantly, this protocol allowed for the long chain 1,1-dibromohept-1-ene to be converted into the corresponding 2-hexylbenzo[d]thiazole in moderate yield. Georg Thieme Verlag Stuttgart, New York.
Regioselectivity in the addition of grignard reagents to bis(2-benzothiazolyl) ketone: C- vs. O-alkylation using aryl grignard reagents
Boga, Carla,Micheletti, Gabriele
experimental part, p. 5659 - 5665 (2010/12/25)
The reaction between bis(2-benzothiazolyl) ketone (1) and a series of ring-substituted phenyl Grignard reagents gives, in considerable amount, the unexpected O-alkylation product derived from the attack of the Grignard reagent to thecarbonyl oxygen atom,
