80491-28-7

Upstream product

• 5873-85-8 Phenylthioessigsaeure-O-methylester 
• 84645-45-4 lithio(trimethylsilyl)diazomethane 
• 61124-61-6 3-phenylpropanal p-tosylhydrazone 
• 104-53-0 3-phenyl-propionaldehyde 
• 19261-37-1 2-chloro-3-phenyl-propionaldehyde 

Downstream Products

• 143772-46-7 3-Methyl-1,2,3-thiadiazolium-5-(α-nitroso)benzylide 
• 143772-42-3 5-Benzoyl-1,2,3-thiadiazole (E)-phenylhydrazone 
• 143772-52-5 3-Methyl-1,2,3-thiadiazolium-5-(α-phenylazo)benzylide 
• 143772-37-6 Phenyl 1,2,3-thiadiazol-5-yl ketone oxime 

Relevant academic research and scientific papers

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.

NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 59. LITHIUM TRIMETHYLSILYLDIAZOMETHANE: A NEW SYNTHON FOR THE PREPARATION OF 5-SUBSTITUTED 1,2,3-THIADIAZOLES

Lithium trimethylsilyldiazomethane smoothly reacts with thionoesters, dithioesters, and carbon disulfide to give 5-substituted 1,2,3-thiadiazoles.

THE REACTION OF α,β-UNSATURATED p-TOSYLHYDRAZONES WITH SULPHUR CHLORIDES

α,β-Unsaturated p-tosylhydrazones react with tetravalent and divalent sulphur chlorides affording 1,2,3-thiadiazoles in good yields.The necessary methylene group adjacent to the C=N bond may be provided by electrophilic addition of a hydrogen chloride molecule.The major difference in the product distribution in the reactions of unsaturated and saturated p-tosylhydrazones with SOCl2, SCl2 or S2Cl2 is observed with substrates prepared from methyl ketones; on using SOCl2 a more favourable distribution of compounds derived from cyclization on the methyl group is obtained.