40753-13-7

Usage

Chemical Properties

Light yellow solid

InChI:InChI=1/C8H5BrN2S/c9-7-3-1-6(2-4-7)8-5-12-11-10-8/h1-5H

Upstream product

• 120445-88-7 C₉H₁₀BrN₃O 
• 99-90-1 para-bromoacetophenone 
• 64273-20-7 isopropylidene-hydrazinecarbothioic acid S-[2-(4-bromo-phenyl)-2-oxo-ethyl] ester 
• 1261591-00-7 N'-[(1E)-1-(4-bromophenyl)ethylidene]-2-(quinolin-8-yloxy)acetohydrazone 
• 75230-51-2 4-bromoacetophenone tosylhydrazone 
• 4209-02-3 1-(4-bromophenyl)-2-chloroethan-1-one 
• 1402672-01-8 C₁₇H₂₄BrN₄O₂S⁽¹⁺⁾*CF₃O₃S^(1-) 
• 99-73-0 para-bromophenacyl bromide 
• 192436-83-2 4-bromo-N-methoxy-N-methylbenzamide 
• 64273-24-1 5-(4-bromo-phenyl)-3,6-dihydro-[1,3,4]thiadiazin-2-one 

Downstream Products

• 64273-27-4 4-([1,1′-biphenyl]-4-yl)-1,2,3-thiadiazole 
• 1088408-48-3 7(S)-7-deoxy-7-(4-(1,2,3-thiadiazol-4-yl)phenylthio)lincomycin 

Relevant academic research and scientific papers

Synthesis method of 1, 2, 3-thiadiazole derivative

The invention belongs to the technical field of compound preparation, and discloses a synthesis method of a 1, 2, 3-thiadiazole derivative. The synthesis method of the 1, 2, 3-thiadiazole derivative comprises the following steps: taking an N-tosylhydrazon

Diiiodine/Potassium Persulfate Mediated Synthesis of 1,2,3-Thiadiazoles from N -Tosylhydrazones and a Thiocyanate Salt as a Sulfur Source under Transition-Metal-Free Conditions

A highly efficient method for the synthesis of 1,2,3-thiadiazoles has been developed by utilizing readily available tosylhydrazones and ammonium thiocyanate with ecofriendly EtOH as the solvent at room temperature. The reaction shows a wide scope of subst

Selective transformations of 2-(p-toluenesulfonyl)-N-tosylhydrazones to substituted 1,2,3-thiadiazoles

Selective transformations of 2-(p-toluenesulfonyl)-N-tosylhydrazones with different sulfur sources have been established. A series of 4-aryl-1,2,3-thiadiazoles and novel 4-aryl-5-tosyl-1,2,3-thiadiazoles were selectively constructed by the adjustment of reaction conditions. These protocols feature short reaction time, good compatibility of functional group, easily available materials, and good selectivity.

Metal- and Oxidant-free Electrosynthesis of 1,2,3-Thiadiazoles from Element Sulfur and N-tosyl Hydrazones

A metal- and oxidant-free electrochemical method for synthesizing 1,2,3-thiadiazoles by inserting element sulfur into N-tosyl hydrazones is reported. This electrochemical transformation engages electrons as reagents to achieve redox processes, and avoid e

Perylenequinonoid-Catalyzed [4 + 1] and [4 + 2] Annulations of Azoalkenes: Photocatalytic Access to 1,2,3-Thiadiazole/1,4,5,6-Tetrahydropyridazine Derivatives

Nitrogen-containing heterocycles are especially considered "privileged" structural scaffolds for the development of new drugs. However, traditional methods of organic synthesis are mainly based on thermal cycloaddition reaction; thus, the exploration of n

Cascade Trisulfur Radical Anion (S3?-) Addition/Electron Detosylation Process for the Synthesis of 1,2,3-Thiadiazoles and Isothiazoles

Trisulfur radical anion (S3?-) mediated reactions with in situ formed azoalkenes and α,β-usaturated N-sulfonylimines for the construction of 1,2,3-thiadiazoles and isothiazoles has been developed. S3?- is in situ generated from potassium sulfide in DMF. These two approaches provide a new, safe, and simple way to construct 4-subsituted 1,2,3-thiadiazoles, 5-subsituted 1,2,3-thiadiazoles, and isothiazole in good yields. The reactions include the formation of the new C-S and N-S bonds via S3?- addition and electron detosylation under mild conditions.

Coupled Flavin-Iodine Redox Organocatalysts: Aerobic Oxidative Transformation from N-Tosylhydrazones to 1,2,3-Thiadiazoles

A bioinspired two-component redox organocatalyst system using 1,10-bridged flavinium and NH4I was developed to perform environmentally friendly aerobic oxidative ring formation of 1,2,3-thiadiazoles from N-tosylhydrazones and sulfur. The redox

TBAI-Catalyzed Reaction between N-Tosylhydrazones and Sulfur: A Procedure toward 1,2,3-Thiadiazole

A TBAI-catalyzed reaction between N-tosyl hydrazone and sulfur was developed, leading to 1,2,3-thiadiazoles in moderate to good yields. It represents a facile and practical procedure to access thiadiazole under metal-free conditions. This procedure serves

Ionic liquid as soluble support for synthesis of 1,2,3-thiadiazoles and 1,2,3-selenadiazoles

A convenient synthesis of 1,2,3-thiadiazoles and 1,2,3-selenadiazoles was achieved using an ionic liquid as a novel soluble support. Ionic liquid-supported sulfonyl hydrazine was synthesized and reacted with a number of ketones to afford the corresponding ionic liquid-supported hydrazones that were converted to 1,2,3-thiadiazoles in the presence of thionyl chloride. The reaction of ionic liquid-supported hydrazones with selenium dioxide in acetonitrile afforded 1,2,3-selenadiazoles. The advantages of this methodology were the ease of workup, simple reaction conditions, and high purity.

Synthesis, characterization, antiamoebic activity and cytotoxicity of novel 2-(quinolin-8-yloxy) acetohydrazones and their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives)

A series of 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives were synthesized by the cyclization of novel 2-(quinolin-8-yloxy) acetohydrazones. In vitro antiamoebic activity was performed against HM1: IMSS strain of Entamoeba histolytica. The results showed that all the 2-(quinolin-8-yloxy) acetohydrazones were more active than their cyclized products (1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives). SAR showed that the compounds having quinoline ring and hydrazone linkage with free N-H group are responsible for higher antiamoebic activity. The cytotoxic studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds were nontoxic at the concentration range of 1.56-50 μM.