70540-36-2Relevant academic research and scientific papers
Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
, p. 3398 - 3402 (2021/06/25)
Aerobic visible-light induced intermolecular S?N bond construction has been achieved without the addition of photosensitizer, metal, or base. With this strategy, 1,2,4-thiadiazoles can be obtained from thioamides. Preliminary mechanistic investigation suggested that the excited state of thioamides undergoes a single-electron-transfer (SET) process to afford thioamidyl radicals, which can be further transformed into a 1,2,4-thiadiazole through desulfurization and oxidative cyclization. The reaction has good functional group tolerance and represents a green method for the construction of S?N bonds.
Visible-light promoted serendipitous synthesis of 3,5-diaryl-1,2,4-thiadiazoles via oxidative dimerization of thiobenzamides
Aggarwal, Ranjana,Hooda, Mona
, (2021/11/30)
In the present manuscript, we report serendipitous synthesis of 3,5-diaryl-1,2,4-thiadiazoles with the aid of a household compact fluorescent lamp (CFL). In presence of α-bromo-β-diketone, thiobenzamides undergo oxidative dimerization to generate corresponding 3,5-diaryl-1,2,4-thiadiazoles in excellent yields in just 5 min instead of expected 2-aryl-4-methyl-5-acylthiazoles. Inhibition of the reaction by free radical scavenger (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) indicates that the dimerization takes place through a free radical process. The synthetic value of the developed protocol was established by synthesizing over eleven diverse 1,2,4-thiadiazoles in a shorter duration with exceptionally high purity and simple work-up procedure under environment benign additive-free conditions.
Highly efficient synthesis of 1,2,4-thiadiazoles from thioamides utilizing tetra(n-butyl)ammonium peroxydisulfate
Lee, Kieseung,Lee, Richard S.,Kim, Yong Hae
supporting information, p. 1774 - 1779 (2020/06/01)
A new synthetic approach to 1,2,4-thiadiazoles using tetra(n-butyl)ammonium peroxydisulfate via oxidative dimerization of thioamides is described. This new oxidative protocol is simple, highly efficient, and allows the practical synthesis of 1,2,4-thiadiazoles from various primary thioamides in good to excellent yields.
Tribromo Phloroglucinol as a Novel and Highly Efficient Reagent for the Conversion of Benzothioamides to the Corresponding 1,2,4-Thiadiazoles
Zali-Boeini, Hassan,Mansouri, Seyed Gholamhossein
, p. 1681 - 1687 (2015/06/25)
(Chemical Equation Presented) 2,4,6-Tribromo-1,3,5-trihydroxybenzene (TBTHB) as a reagent was efficiently reacted with 6 molar equivalents of benzothioamides in dimethyl sulfoxide (DMSO), and the corresponding 3,5-diaryl-1,2,4-thiadiazoles were obtained in almost quantitative yields (91-98%) and in short times (15-20 min) with the formation of hexahydroxybenzene as a rather valuable by-product. 2015
Copper(II)-mediated homocoupling of thioamides for the synthesis of 1,2,4-thiadiazoles
Sun, Yadong,Wu, Wanqing,Jiang, Huanfeng
, p. 4239 - 4243 (2014/07/21)
A copper(II)-mediated highly selective oxidative cyclization reaction of thioamides to provide 3,5-disubstituted 1,2,4-thiadiazoles was developed. The copper species plays a key role in this transformation and different functional groups are tolerated under the optimal reaction conditions. Copyright
A novel process for the synthesis of 3,5-diaryl-1,2,4-thiadiazoles from aryl nitriles
Noei, Jalil,Khosropour, Ahmad Reza
, p. 9 - 11 (2013/02/21)
A novel and efficient process for the synthesis of 3,5-diaryl-1,2,4- thiadiazoles from aryl nitriles in 1-butyl-3-methylimidazolium bromide promoted by (NH4)2S and TCT-DMSO is described.
Highly efficient synthesis of 3,5-disubstituted 1,2,4-thiadiazoles using pentylpyridinium tribromide as a solvent/reagent ionic liquid
Zali-Boeini, Hassan,Shokrolahi, Arash,Zali, Abbas,Ghani, Kamal
experimental part, p. 165 - 170 (2012/06/01)
In this paper, a facile and highly efficient synthesis of 3,5-disubstituted 1,2,4-thiadiazoles by oxidative dimerization of thioamides using pentylpyridinium tribromide is reported.
Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets
Mayhoub, Abdelrahman S.,Marler, Laura,Kondratyuk, Tamara P.,Park, Eun-Jung,Pezzuto, John M.,Cushman, Mark
experimental part, p. 510 - 520 (2012/03/10)
Chemoprevention is an approach to decrease cancer morbidity and mortality through inhibition of carcinogenesis and prevention of disease progression. Although the trans stilbene derivative resveratrol has chemopreventive properties, its action is compromised by weak non-specific effects on many biological targets. Replacement of the stilbene ethylenic bridge of resveratrol with a 1,2,4-thiadiazole heterocycle and modification of the substituents on the two aromatic rings afforded potential chemopreventive agents with enhanced potencies and selectivities when evaluated as inhibitors of aromatase and NF-κB and inducers of quinone reductase 1 (QR1).
Highly efficient synthesis of 3,5-diaryl-1,2,4-thiadiazoles in water-wet paste conditions
Boeini, Zali Hassan
experimental part, p. 2932 - 2938 (2011/09/12)
1,3-Dibromo-5,5-diphenylimidazolidine-2,4-dione (N,N'-dibromo phenytoin) was efficiently used for the rapid conversion of thiobenzamides to the corresponding 3,5-diaryl-1,2,4-thiadiazoles in water-wet paste conditions. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.
