243456-06-6

Upstream product

• 26197-93-3 p-bromothiobanzamide 
• 623-00-7 4-bromobenzenecarbonitrile 
• 57626-33-2 2-bromo-1-phenyl-1,3-butanedione 

Relevant academic research and scientific papers

Hypervalent iodine in synthesis. 84. Facile synthesis of 3,5-disubstituted 1,2,4-thiadiazoles by oxidative dimerization of thioamides using polymer-supported iodobenzene diacetate

A facile synthesis of 3,5-disubstituted 1,2,4-thiadiazoles by oxidative dimerization of thioamides using polymer-supported iodobenzene diacetate has been reported.

Aerobic Visible-Light Induced Intermolecular S?N Bond Construction: Synthesis of 1,2,4-Thiadiazoles from Thioamides under Photosensitizer-Free Conditions

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

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.

Fully Conjugated Donor-Acceptor Covalent Organic Frameworks for Photocatalytic Oxidative Amine Coupling and Thioamide Cyclization

Covalent organic frameworks (COFs) are promising candidates as heterogeneous photocatalysts because of their porosity and tunable light absorption. The photostability and charge separation of COFs are highly important to improve the efficiency of photocatalytic transformation. In this work, a fully conjugated donor-acceptor COF is constructed with a benzothiadiazole unit, which exhibits high stability and enhanced charge separation. The prepared COF can efficaciously produce superoxide radical anions under air and visible light, which mediate the photocatalytic oxidative amine coupling and cyclization of thioamide to 1,2,4-thiadiazole in moderate to high yield and high recyclability (18 examples). This study demonstrates the great capacity of fully conjugated COFs with a D-A structure for light-driven organic synthesis.

Tribromo Phloroglucinol as a Novel and Highly Efficient Reagent for the Conversion of Benzothioamides to the Corresponding 1,2,4-Thiadiazoles

(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

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

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

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

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

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.