1256158-53-8Relevant articles and documents
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)
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.
New synthesis of 2-aroylbenzothiazolesviametal-free domino transformations of anilines, acetophenones, and elemental sulfur
Doan, Khang V.,Doan, Son H.,Huynh, Tien V.,Luong, Ngoc T. K.,Nguyen, Duyen T. P.,Nguyen, Tung T.,Phan, Nam T. S.
, p. 18423 - 18433 (2020/06/08)
A new synthesis of 2-aroylbenzothiazolesviaiodine-promoted domino transformations of anilines, acetophenones, and elemental sulfur was demonstrated. The highlights of this tandem synthesis are (1) easily available anilines and acetophenones as feedstock;
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.
