15165-37-4

Upstream product

• 2547-66-2 1,3,5-Tribenzyl-1,3,5-triazacyclohexane 
• 55738-12-0 1-benzyl-4,5-dimethyl-1H-imidazole 3-oxide 
• 54439-99-5 tert-butyl-isopropyl-thioketene 

Downstream Products

• 1138238-24-0 3-benzyl-2,3-dihydro-4,5-dimethyl-2-thioxo-1H-imidazole-1-carboxylic acid N-phenylamide 
• 1138238-20-6 (Z)-2-[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]but-2-enedioic acid dimethyl ester 
• 1349129-39-0 2-[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]acetohydrazide 
• 1349129-72-1 2-[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]-N'-[(E)-(4-methoxyphenyl)methylidene]acetohydrazide 
• 1349129-73-2 2-[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]-N'-[(E)-(4-(dimethylamino)phenyl)methylidene]acetohydrazide 
• 1349129-74-3 2-[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]-N'-cyclohexylideneacetohydrazide 
• 1449684-45-0 2-{[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]acetyl}-N-(4-fluorophenyl)hydrazinecarboselenoamide 
• 1449684-46-1 2-{[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]acetyl}-N-(4-methoxyphenyl)hydrazinecarboselenoamide 
• 1449684-53-0 5-{[(1-benzyl-4,5-dimethyl-1H-imidazol-2-yl)sulfanyl]methyl}-2,4-dihydro-4-(4-methoxyphenyl)-3H-1,2,4-triazole-3-selone 

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).