166593-11-9

Upstream product

• 333-20-0 potassium thioacyanate 
• 49656-78-2 2-methylamino-1-phenyl-1-propanone hydrochloride 
• 25355-34-4 1-phenyl-propane-1,2-dione 1-oxime 
• 215675-50-6 1,5-dimethyl-4-phenylimidazole 3-oxide 

Downstream Products

• 1138238-22-8 (Z)-2-[(1,5-dimethyl-4-phenyl-1H-imidazol-2-yl)sulfanyl]but-2-enedioic acid dimethyl ester 
• 1449684-44-9 2-{[(1,5-dimethyl-4-phenyl-1H-imidazol-2-yl)sulfanyl]acetyl}-N-(4-fluorophenyl)hydrazinecarboselenoamide 
• 1449684-43-8 2-{[ (1,5-dimethyl-4-phenyl-1H-imidazol-2-yl)sulfanyl]acetyl}-N-(4-methoxyphenyl)hydrazinecarboselenoamide 
• 1449684-49-4 2-[(1,5-dimethyl-4-phenyl-1H-imidazol-2-yl)sulfanyl]acetohydrazide 
• 62576-13-0 1,5-0dimethyl-4-phenyl-1H-imidazole 

Relevant academic research and scientific papers

Ambivalent nucleophilicity of 1,4,5-trisubstituted imidazole-2-thiones in reactions with dimethyl acetylenedicarboxylate and phenylisocyanate

The 1,4,5-trisubstitued 2,3-dihydro-1H-imidazole-2-thiones 1 react with electrophilic reagents via the S- or the N(3)-atom. The reaction with dimethyl acetylenedicarboxylate in methanol at room temperature occurs by the nucleophilic addition of the S-atom

First Examples of Reactions of Azole N-Oxides with Thioketones: A Novel Type of Sulfur-Transfer Reaction

The reactions of 1,4,5-trisubstituted imidazole 3-oxides 1a-k with cyclobutanethiones 5a,b in CHCl3 at room temperature give imidazole-2(3H)-thiones 9a-k in high yield. The second product formed in this reaction is 2,2,4,4-tetramethylcyclobutane-1,3-dione (6a; Scheme 2). Similar reactions occur with 1 and adamantanethione (5c) as thiocarbonyl compound, as well as with 1,2,4-triazole-4-oxide derivative 10 and 5a (Scheme 3). A reaction mechanism by a two-step formation of the formal cycloadduct of type 7 via zwitterion 16 is proposed in Scheme 5. Spontaneous decomposition of 7 yields the products of this novel sulfur-transfer reaction. The starting imidazole 3-oxides are conveniently prepared by heating a mixture of 1,3,5-trisubstituted hexahydro-1,3,5-triazines 3 and α-(hydroxyimino) ketones 2 in EtOH (cf. Scheme 1). As demonstrated in the case of 9d, a 'one-pot' procedure allows the preparation of 9 without isolation of the imidazole 3-oxides 1. The reaction of 1c with thioketene 12 leads to a mixture of four products (Scheme 4). The minor products, 9c and the ketene 15, result from an analogous sulfur-transfer reaction (Path a in Scheme 5), whereas the parent imidazole 14 and thiiranone 13 are the products of an oxygen-transfer reaction (Path b in Scheme 5).

Novel imidazoles and hydantoins moderately strained by incorporation with 2-azabicyclo[2.2.1]heptene skeleton

The reactions of 3-acyl-2-azabicyclo[2.2.1]hept-5-enes with phenyl isocyanate, phenyl isothiocyanate, and ethoxycarbonyl isothiocyanate followed by cyclization reactions under basic conditions respectively provided a hydantoin, a thiohydantoin, and a 1,3-