4057-61-8

Usage

Class

Organic heterocyclic compound

Subclass

1,2,5-thiadiazoles

Structure

Five-membered ring containing one sulfur atom, two nitrogen atoms, and two carbon atoms

Applications

Building block in the synthesis of pharmaceuticals, agrochemicals, and materials science

Versatility

Valuable intermediate for the production of various functional materials and bioactive compounds

Biological activities

Anti-cancer, anti-inflammatory, and anti-microbial properties

Potential

Promising target for drug discovery and development

Upstream product

• 451-40-1 phenyl benzyl ketone 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 4057-62-9 3-phenyl-1,2,5-thiadiazole 
• 5344-88-7 benzil monohydrazone 
• 89929-37-3 3,5-diphenyl-1,4,2,6-dithiadiazine 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 23431-14-3 3,4-diphenyl-1,2,5-thiadiazole 2-oxide 
• 134-81-6 benzil 
• 886-38-4 diphenylcyclopropenone 
• 2227-79-4 benzenecarbothioamide 
• 88089-52-5 (Z)-((1,2-diphenylvinyl)oxy)trimethylsilane 
• 501-65-5 diphenyl acetylene 
• 23873-81-6 benzildioxime 
• 5700-60-7 1,2-Diphenylethylenediamine 

Downstream Products

• 668-94-0 4,5-diphenyl-1H-imidazole 
• 83392-70-5 3,4-Diphenyl-[1,2,5]telluradiazole 

Relevant academic research and scientific papers

Unexpected production of 2,4,6-triphenyl-1,3,5-triazine in the electroreduction of 3,4-diphenyl-1,2,5-thiadiazole 1-oxide. Theoretical estimation of reactive sites for 1-oxide and 1,1-dioxide 1,2,5-thiadiazoles

3,4-Diphenyl-1,2,5-thiadiazole 1-oxide (1a) in acetonitrile solution is electroreduced to 2,4,6-triphenyl-1,3,5-triazine and 3,4-diphenyl-1,2,5- thiadiazole. This behavior is very different from that of similar compounds with other oxidation states of the

1,2,5-Thiadiazole 2-oxides: Selective synthesis, structural characterization, and electrochemical properties

A new general procedure for the selective synthesis of 1,2,5-thiadiazole 2-oxides (including fused derivatives) 8a,b,c,g,h from the reaction of vic-glyoximes with S2Cl2 and pyridine in acetonitrile was elaborated together with general procedure for the synthesis of 1,2,5-thiadiazoles 7a-i, 10, 12, and 14 from the same starting materials and reagents. Molecular structures of 3,4-dimethyl-1,2,5-thiadiazole 2-oxide 8a and [1,2,5]thiadiazolo[3,4-b]quinoxaline 10 were confirmed by single-crystal X-ray diffraction. Electrochemical properties of 1,2,5-thiadiazole 2-oxides 8 were studied by cyclic voltammetry and different behavior was observed for monocyclic and benzo-fused derivatives. With compounds 8g and 17, previously unknown deoxygenation of 2,1,3-benzothiadiazole 1-oxides was discovered by electrochemical reduction, and resulted 2,1,3-benzothiadiazoles 7g and 19 were detected in the forms of their radical anions by EPR spectroscopy combined with DFT calculations.

Reaction of trithiazyl trichloride with alkenes and alkynes

Alkenes and alkynes react readily with trithiazyl trichloride 1 to give 1,2,5-thiadiazoles 2 in one step. Thus 3-amino-1,2,5-thiadiazole 5 is now readily available from N-vinylphthalimide and 1 in two steps. Cyclic alkenes react similarly to give fused thiadiazoles (7, 12) and phenanthrene gives the phenanthrothiadiazole 16. Tetra-substituted alkenes such as 13 appear to give the analogous 3,4-dihydrothiadiazoles (e.g. 14) which spontaneously ring open to give readily hydrolysed bis(methyleneamino) sulfides (e.g. 15). A simple set of mechanisms is proposed for all of these reactions.

Organic Heterocyclothiazenes. Part 2. Reaction of Tetrasulphur Tetranitride with Phenylacetylene and Diphenylacetylene

The reaction of S4N4 with diphenylacetylene in boiling toluene has been found to give 3,4-diphenyl-1,2,5-thiadiazole (1) as the major product and 3,5-diphenyl-1,4,2,6-dithiadiazine (4), a new heterocyclic system, as a minor product.The same reaction with

A-ALKYLATION, ALKENYLATION, AND ARYLATION OF 1,2,5-THIADIAZOLES

A new synthetic method of 1,2,5-thiadiazoles is reported, which affording mono- or disubstituted derivatives by one pot procedure, clarifies unknown aspects of the 1,2,5-thiadiazole ring reactivity.

Reactions of Tetrasulphur Tetranitride with Alkynes; 1,4,2,6-Dithiadiazines and 1,3,2-Dithiazoles

Reaction of S4N4 with diphenylacetylene and phenylacetylene gives two new, thermally stable heterocyclic systems, the 1,4,2,6-dithiadiazine (3) and the 1,3,2-dithiazolylimine (7), respectively, as minor products; these structures, determined by X-ray diff

SULFUR NITRIDE IN ORGANIC CHEMISTRY. 12. THE REACTION OF N4S4 WITH 1-ARYL-1-TRIMETHYLSILYLOXYETHYLENES AFFORDING 3-HYDROXY-4-ARYL-1,2,5-THIADIAZOLES

Reaction of N4S4 with 1-aryl-1-trimethylsilyloxyethylenes (1a-1e) gave 3-hydroxy-4-aryl-1,2,5-thiadiazoles (2a-2e) though the yields were low. 3-Amino-4-thienyl-1,2,5-thiadiazole (3) was obtained as a minor product.

REACTION OF BENZILMONOHYDRAZONE WITH S4N4, A CORRECTION

Reaction of benzilmonohydrazone (1) with S4N4 gives the azine (6) and not the 2-H-imidazole (2); this invalidates the claim that (2) is not the intermediate in the formation of N-benzoyltriphenylimidazole from benzil and ammonia.S4N4 converts diphenylketene into thiobenzophenone.

Sulfur Nitride in Organic Chemistry. 9. The Reaction of Tetrasulfur Tetranitride with Benzyl Ketones. Preparation of 3,4-Disubstituted-1,2,5-thiadiazoles

The reaction of tetrasulfur tetranitride (1) with various aryl and benzyl ketones (2a-o), oxindole (11), benzyl α-pyridyl ketone (12) and α-phenacylpyridine (13) afforded the corresponding 1,2,5-thiadiazoles (3a-n, 11 and 14).The scope and limitations of the above reaction were investigated and the evidences suggesting the radical anion mechanism are presented.