4115-26-8

Upstream product

• 103-85-5 monophenylthiourea 
• 112476-37-6 benzenetellurinyl trifluoroacetate 
• 14779-12-5 1,2-diimido-μ-disulfido-dicarbonic acid dianilide; dihydrobromide 
• 74961-10-7 1-phenyl-1-phenylcarbamimidoyl-thiourea 

Downstream Products

• 22713-97-9 N³,N⁵-diphenyl-1,2,4-thiadiazole-3,5-diamine 
• 56014-04-1 4,5-bis(methoxycarbonyl)-2-(phenylamino)thiazole 
• 56014-03-0 4,5-dibenzoyl-2-(phenylamino)thiazole 
• 73350-40-0 Dost's keto-compound 
• 75351-01-8 (3-anilino-4-phenyl-4H-[1,2,4]thiadiazol-5-ylidene)-phenyl-thiourea 
• 56014-05-2 2-anilino-4-phenyl-thiazole-5-carboxylic acid methyl ester 
• 59026-95-8 2-anilino-1,6-diphenyl-1,5(7)-dihydro-4λ⁴-[1,2,4]thiadiazolo[5,1-e][1,2,4]thiadiazole 
• 17467-60-6 phenyl-3-(phenyl)-[1,2,4]thiadiazol-5-amine 
• 59236-40-7 N-nitroso-4-phenyl-3-phenylimino-1,2,4-thiadiazolidine-5-imine 
• 56014-26-7 N⁵-phenyl-N³-p-tolyl-[1,2,4]thiadiazole-3,5-diamine 

Relevant academic research and scientific papers

Synthesis and antimicrobial activity of N-glucosylated derivatives of thiadiazolidines

A series of new 1-(3-arylimino-4-aryl-5-imino-1,2,4-thiadiazolidines)-3-tetra-Obenzoyl- β-D-glucosyl carbamides were synthesized by the interaction of tetra-Obenzoyl- β-D-glucosyl isocyanate with 3-arylimino-4-aryl-5-imino-1,2,4-thiadiazolidines. The iden

Oxidative azacyclization of 1-monosubstituted thioureas in reaction with [bis(acyloxy)iodo]arenes to form 1,2,4-thiadiazole derivatives

For the first time, derivatives of 1,2,4-thiadiazoles have been obtained by the reaction of [bis(acyloxy)iodo]arenes with 1-monosubstituted thioureas. 1-Acetylthiourea is subject to intermolecular azacyclization to form 3,5-bis-(acetylamino)-1,2,4-thiadia

Mechanism of the formation of 1,2,4-thiadiazoles by condensation of aromatic thioamides and of N-substituted thioureas

The condensation reaction of thiobenzamide, (as well as thionicotinamide and isothionicotinamide) in the presence of dimethyl sulfoxide and of an acid, affords 3,5-diphenyl-1,2,4-thiadiazole. Under the same experimental conditions, N-substituted thioureas are also condensed to 1,2,4-thiadiazole derivatives; their structure is ascertained by spectroscopic properties and by X-ray diffraction. Some information on the mechanism of thiadiazoles formation from both starting classes of compounds, thiobenzamides and N- substituted thiourea, is collected and discussed.

Condensation of thiourea derivatives with carbonyl compounds: One-pot synthesis of N-alkyl-1, 3-thiazol-2-amines and of 3-alkyl-1, 3-thiazolimines

The reactions of ketones and AT-substituted thioureas, in the presence of HC1 (or HBr) and DMSO afford mixtures of the title compounds which are easily separated on a silica gel column. This method avoids the classical use of a-haloketones. The mechanism of these reactions involves the enolization of ketones and the activation of thiourea sulfur, probably by oxygen transfer from DMSO.

Benzenetellurinic Mixed Anhydrides as Mild Oxidizing Agents

Three benzenetellurinic mixed anhydrides. i. e. benzenetellurinyl acetate, trifluoroacetate, and trifluoromethanesulfonate, have been found to be mild oxidizing agents for various substrates such as thiol, phosphine, acyloin, α-hydroxy ester, catechol, hydroquinone, thiourea, and thioamide.The reactions towards the last two substrates are highly chemoselective, depending on both the reagent and substrate.

Polymer-Supported Diaryl Selenoxide and Telluroxide as Mild and Selective Oxidizing Agents

Polystyrene-bound diaryl selenoxide and telluroxide have been prepared, which behaved as mild oxidizing agents for thiols to disulfide, phosphines to phosphine oxides, hydroquinone and catechol to p- and o-benzoquinones, and thioketones to oxo compounds.The telluroxide completed these reactions in shorter periods or under milder conditions than the selenoxide.In addition, they effected novel solvent-dependent reactions of thioamides involving thioureas to 1,2,4-thiadiazoles or to nitriles.In nonacidic solvents, the dehydrosulfurization to nitriles occured in preference to the oxidative dimerization to 1,2,4-thiadiazoles, but an acidic solvent such as acetic acid promoted the latter reaction.

N-NITROSAMINES AS REAGENTS FOR THE =C=S=C=O TRANSFORMATION

N-nitrosopiperidine and N-nitroso-N-methylaniline react in acidic solution with thiocarbonyl compounds to give the corresponding carbonyl analogues.Secondary- and tertiary thioamides, xanthione, thio- and dithiobutyrolactone, thiocoumarin, certain thiourea derivatives, dithio-O,O-thiocarbonic, S,S-trithiocarbonic- and N,N disubstituted thiocarbamic esters are all converted into the corresponding O-analogues.Thiobenzamide and N-phenylthiourea yield 1,2,4-thiadiazoles.All the reactions are run with iodide (I-) as NO+-carrier.The kinetics of the reaction have been studied under pseudo-first order conditions, and the reaction rate is proportional to the Pearson's nucleophilicity parameter of ions.The =C=S =C=O transformation is also found to take place in gastric juice.

THE REACTION OF t-BUTYL HYPOCHLORITE WITH THIOCARBONYL COMPOUND - A CONVENIENT METHOD FOR THE TRANSFORMATION

The reaction of t-butyl hypochlorite with different thiocarbonyl compounds has been studied.Primary thioamides 1a-c give 1,2,4-thiadiazole derivatives.N-Phenylthiourea 4a gives 5-imino-4-phenyl-3-phenylamino-4,5-dihydro-1,2,4-thiadiazoline 15.Secondary and tertiary thioamides 2a-d, N-methyl-2-thiopyrrolidinone 3, N,N'-dicyclohexylthiourea 4b, N,N,N'-trimethylthiourea 4c, 5-ethyl-5-phenylthiobarbituric acid 5, xanthione 7a, Mischler's thioketone 7b, thiocoumarin 8, O-ethylthiobenzoate 9, O,O-diphenylthiocarbonate 10, di-p-tolyl and o-phenylene trithiocarbonates 11 and 12 have all afforded the oxigen analogues.N,N-Dimethyl-S-phenyldithiocarbonate 6 produces a mixture of di-, tri-, and tetrasulfides.A mechanism for the transformation is suggested in accordance with the Hard and Soft Acids and Bases (HSAB) principle.

Bis(p-methoxyphenyl) Selenoxide as a Mild and Selective Oxidizing Agent

The title compound oxidized thiolsto disulfides, sulfides to sulfoxides, hydroquinone or catechol to benzoquinones, and phosphine to phosphine oxide in high yields under very mild conditions.In addition, it functioned as a useful reagent for the syntheses of 1,2,4-thiadiazole derivatives from thioureas or thioamides.