- 2,4,6-Tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine as a new recyclable hypervalent iodine(III) reagent for chlorination and oxidation reactions
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The synthesis of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine, as a new recyclable nonpolymeric analogue of (dichloroiodo)benzene, is achieved in two steps using 2,4,6-trichloro-1,3,5-triazine and 4-iodophenol. The application of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine for the chlorination reaction of various activated arenes, olefin, and 1,3-diketone is demonstrated. The reagent 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine can be applied also for the oxidative synthesis of 1,3,4-oxadiazoles and 1,2,4-thiadiazoles under mild conditions in excellent yields. The recyclability of the 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine was possible owing to the facile recovery and reuse of the coproduced 2,4,6-tris(4-iodophenoxy)-1,3,5- triazine from the reaction mixture due to its practical insolubility in methanol. Georg Thieme Verlag Stuttgart, New York.
- Thorat, Prerana B.,Bhong, Bhagyashree Y.,Karade, Nandkishor Y.
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- Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions
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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.
- Wang, Hui,Xie, Shihua,Zhu, Hongjun,Zhuo, Liang
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supporting information
p. 3398 - 3402
(2021/06/25)
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- Highly efficient synthesis of 1,2,4-thiadiazoles from thioamides utilizing tetra(n-butyl)ammonium peroxydisulfate
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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.
- Lee, Kieseung,Lee, Richard S.,Kim, Yong Hae
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supporting information
p. 1774 - 1779
(2020/06/01)
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- Regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium-catalyzed C-H activation
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A regioselective C-C cross-coupling of 1,2,4-thiadiazoles with maleimides through iridium catalysis was developed. This transformation tactically linked the 1,2,4-thiadiazoles and succinimides together, and the novel molecules formed may have potential biological activity.
- Tian, Ting,Dong, An-Shun,Chen, Dan,Cao, Xian-Ting,Wang, Guannan
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supporting information
p. 7664 - 7668
(2019/08/30)
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- Electrochemical Synthesis of 3,5-Disubstituted-1,2,4-thiadiazoles through NH4I-Mediated Dimerization of Thioamides
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A electrochemical method for the synthesis of 3,5-disubstituted-1,2,4-thiadiazoles through NH4I-mediated dimerization of thioamides is reported. Using the inexpensive NH4I as electrolyte and catalyst, this electrosynthesis approach requires no oxidizing agents and enables the convenient production of diverse 1,2,4-thiadiazoles products. The approach is an example of S?N bond construction through the electrochemical method. (Figure presented.).
- Wang, Zi-Qiang,Meng, Xiu-Jin,Li, Qian-Yu,Tang, Hai-Tao,Wang, Heng-Shan,Pan, Ying-Ming
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supporting information
p. 4043 - 4048
(2018/09/21)
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- A simple method for synthesis of thioamides and application in synthesis of 1,2,4-thiadiazoles
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A novel, simple protocol is disclosed for the synthesis of 1,2,4-thiadiazoles starting from thioamides with Na2-eosin Y-sensitized titanium dioxide as catalyst through visible light irradiation (7 W blue LED light) and only 0.3 mol% catalysts were used. The raw material thioamides is prepared by aryl nitriles and sodium sulfide (Na2S9H2O) in DMF and in this reaction, readily available, inexpensive inorganic salt (Na2S9H2O) serves as the sulfur source and various functional groups of aryl nitriles were well and thioamides were synthesized successfully in gram-scale.
- Cao, Xian Ting,Yang, Huiyong,Zheng, Hui,Zhang, Pengfei
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p. 509 - 517
(2018/03/27)
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- Synthesis of 1,2,4-thiadiazoles by oxidative dimerization of carbothioamides by using oxone
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1,2,4-Thiadiazoles were efficiently synthesized in good yields through the oxidative dimerization of carbothioamides by using Oxone as a readily available, inexpensive, and environmentally safe oxidant. A similar reaction of phenylselenoamide led to the corresponding 1,2,4-phenylselenadiazole in high yield. Copyright
- Yoshimura, Akira,Todora, Anthony D.,Kastern, Brent J.,Koski, Steven R.,Zhdankin, Viktor V.
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supporting information
p. 5149 - 5152
(2014/11/08)
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- Copper(II)-mediated homocoupling of thioamides for the synthesis of 1,2,4-thiadiazoles
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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
- Sun, Yadong,Wu, Wanqing,Jiang, Huanfeng
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p. 4239 - 4243
(2014/07/21)
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- Optimizing thiadiazole analogues of resveratrol versus three chemopreventive targets
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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).
- Mayhoub, Abdelrahman S.,Marler, Laura,Kondratyuk, Tamara P.,Park, Eun-Jung,Pezzuto, John M.,Cushman, Mark
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experimental part
p. 510 - 520
(2012/03/10)
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- Highly efficient oxidative dimerization of thioamides to 3,5-Disubstituted 1,2,4-thiadiazoles mediated by DDQ
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A highly efficient oxidative dimerization of thioamides by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) is reported. The reaction is carried out in ClCH2CH2Cl at room temperature. The corresponding 3,5-disubstituted 1,2,4-thiadiazoles are obtained in good to excellent yields.
- Cheng, Dongping,Luo, Ruiwen,Zheng, Wen,Yan, Jizhong
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experimental part
p. 2007 - 2013
(2012/06/18)
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- CuBr-catalysed oxidative desulfurisation of thiobenzamides
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An efficient oxidative desulfurisation of thioamides by CuBr/TBHP is reported. Thioamides containing alkyl or aryl on the nitrogen undergo desulfurisation and give amides with good yields. Thioamides not containing substituent on the nitrogen undergo desulfurisation and give 1,2,4-thiadiazoles in moderate to good yields.
- Cheng, Dongping,Sun, Ruirui,Yan, Jizhong
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experimental part
p. 210 - 212
(2012/09/08)
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- Solvent-free synthesis of 3,5-di(hetero)aryl-1,2,4-thiadiazoles by grinding of thioamides under oxidative conditions
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An efficient and facile synthesis of 3,5-di(hetero)aryl-1,2,4-thiadiazoles by oxidative dimerisation of thioamides by grinding with NBS under solvent-free conditions at room temperature has been developed. The efficiency of this reaction was demonstrated by the compatibility with trifluoromethyl, methyl, methoxy, chloro, pyridyl and thienyl groups. This method has notable advantages in terms of short reaction times, high yields and is a more practical alternative to the existing methods to access these compounds.
- Xu, Yali,Chen, Jiuxi,Gao, Wenxia,Jin, Huile,Ding, Jinchang,Wu, Huayue
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experimental part
p. 151 - 153
(2010/08/06)
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- REACTION OF SULFUR DICHLORIDE WITH NITRILE IN THE PRESENCE OF LEWIS ACID FORMING 1,2,4-THIADIAZOLE.
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Formation of 3,5-disubstituted 1,2,4-thiadiazoles by the reaction of sulfur dichloride with nitriles in the presence of a Lewis acid was found. For example, 3,5-diphenyl-1,2,4-thiadiazole was obtained with its chlorinated products, 3-o-chlorophenyl-5-phen
- Komatsu,Shibata,Ohshiro,Agawa
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p. 180 - 183
(2007/10/02)
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