26060-23-1Relevant academic research and scientific papers
Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions
Bai, Jin,Yan, Sijia,Zhang, Zhuxia,Guo, Zhen,Zhou, Cong-Ying
supporting information, 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.
Functionalization of activated methylene C-H bonds with nitroarenes and sulfur for the synthesis of thioamides
Do, Nhan T.,Tran, Khoa M.,Phan, Hao T.,To, Tuong A.,Nguyen, Tung T.,Phan, Nam T. S.
supporting information, p. 8987 - 8991 (2019/10/28)
We report a method to obtain arylthioamides by the functionalization of sp3 C-H bonds in phenylacetic acids and benzyl alcohols. Reactions proceeded without the use of any solvents and were compatible with many functionalities and heterocycles. These conditions allow for a rapid synthesis of thioamides from simple, commercial substrates.
Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer
Xu, Ze-Ming,Li, Hong-Xi,Young, David James,Zhu, Da-Liang,Li, Hai-Yan,Lang, Jian-Ping
supporting information, p. 237 - 241 (2019/01/10)
Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.
Decarboxylative thioamidation of arylacetic and cinnamic acids: A new approach to thioamides
Guntreddi, Tirumaleswararao,Vanjari, Rajeshwer,Singh, Krishna Nand
supporting information, p. 3624 - 3627 (2014/08/05)
A new decarboxylative strategy has been developed for the synthesis of thioamides via a three-component reaction involving arylacetic or cinnamic acids, amines and elemental sulfur powder, without the need of a transition metal and an external oxidant.
Sulfonic acid functionalized nano Γ-Al 2O 3: A new, efficient, and reusable catalyst for synthesis of thioamides
Yin, Zhikui,Zheng, Bin,Ai, Fang
, p. 1412 - 1420 (2013/10/08)
Sulfonic acid functionalized nano γ-Al2O3 is easily prepared by the reaction of nano γ-Al2O3 with 1,3-propane sulfone. This reagent can be used as an eficient catalyst for the synthesis of thioamides. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered for several times.
Nano n -propylsulfonated magnetic γ-Fe2O3 as an efficient and reusable catalyst for the synthesis of thioamides
Yin, Zhikui,Zheng, Bin
, p. 527 - 531 (2013/10/21)
One-pot three-component reactions of aldehydes, amines, and sulfur are carried out in the presence of nano n-propylsulfonated magnetic γ-Fe2O3 as a catalyst for the synthesis of biologically interesting thioamide derivatives. The value of this catalytic method lies in its mild reaction catalyst and conditions, good yields, and ease of handling.
Palladium-catalyzed C-H cyclization in water: A milder route to 2-arylbenzothiazoles
Inamoto, Kiyofumi,Nozawa, Kanako,Kondo, Yoshinori
supporting information; experimental part, p. 1678 - 1682 (2012/07/17)
Water was successfully employed as a reaction medium in palladium-catalyzed C-H cyclization of thiobenzanilides. Reactions efficiently proceeded under considerably mild conditions such as 40 °C in water, providing a more practical, greener method for the synthesis of 2-arylbenzothiazoles. For some substrates, the addition of an amphiphilic surfactant greatly enhanced the process. The method represents a rare example of palladium-catalyzed C-H functionalization processes performed in water. Georg Thieme Verlag Stuttgart · New York.
Sulfated tungstate: An efficient catalyst for synthesis of thioamides via Kindler reaction
Pathare, Sagar P.,Chaudhari, Pramod S.,Akamanchi, Krishnacharya G.
experimental part, p. 125 - 129 (2012/07/03)
New application of sulfated tungstate, a mildly acidic solid inorganic acid, as reusable heterogeneous catalyst for efficient Kindler reaction, a three component reactions of aldehydes, amines and sulfur, for synthesis of thioamides is discussed.
Palladium-catalyzed synthesis of 2-substituted benzothiazoles via a C-H functionalization/intramolecular C-S bond formation process
Inamoto, Kiyofumi,Hasegawa, Chisa,Hiroya, Kou,Doi, Takayuki
supporting information; experimental part, p. 5147 - 5150 (2009/05/30)
(Chemical Equation Presented) Catalytic synthesis of 2-substituted benzothiazoles from thiobenzanilides was achieved in the presence of a palladium catalyst through C-H functionalization/C-S bond formation. This method features the use of a novel catalytic system consisting of 10 mol % of Pd(II), 50 mol % of Cu(I), and 2 equiv of Bu4NBr that produced variously substituted benzothiazoles in high yields with good functional group tolerance.
Efficient synthesis of thiobenzanilides by Willgerodt-Kindler reaction with base catalysts
Okamoto, Ken,Yamamoto, Takakazu,Kanbara, Takaki
, p. 2687 - 2690 (2008/02/11)
Willgerodt-Kindler reaction between anilines and benzaldehydes readily proceeded in the presence of catalytic amount of Na2S·9H 2O to give thiobenzanilides in moderate to good yields. The base catalyst was also available for preparation of primary thiobenzamide. Georg Thieme Verlag Stuttgart.
