134650-98-9

Upstream product

• 134650-72-9 N-benzyl-N'-(3,5-dimethylisoxazol-4-yl)thiourea 
• 321309-27-7 4-isothiocyanato-3,5-dimethyl-1,2-oxazole 
• 100-46-9 benzylamine 
• 10181-56-3 2,2,4,4-tetramethylcyclobutane-1,3-dithione 
• 1310826-04-0 4-acetyl-1-benzyl-5-methyl-1H-imidazole 3-oxide 
• 2547-66-2 1,3,5-Tribenzyl-1,3,5-triazacyclohexane 
• 29917-12-2 Isonitrosoacetylacetone 

Relevant academic research and scientific papers

Synthesis of new imidazole 3-oxides; unexpected deoxygenation of some derivatives in the reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione

Whereas the reaction of a series of 1,4,5-trisubstituted imidazole 3-oxides with 2,2,4,4-tetramethylcyclobutane-1,3-dithione gave the corresponding imidazole-2-thiones by a sulfur-transfer reaction via [2+3] cycloaddition, an unexpected deoxygenation occurred in the case of 4-acetyl-1-(adamantan-1-yl)- 5-methylimidazole 3-oxide. It was shown that the presence of an electronwithdrawing substituent at C(4) and the bulky 1-adamantyl group at N(1) are necessary to enable this reaction course. A reaction mechanism via a zwitterion, followed by a 1,3-cyclization and elimination of an oxathiirane, is proposed.

Transformations in the isoxazole series: Synthesis of substituted 2-aminothiazoles

Substitued N-(isoxazol-4-yl)thioureas 1 undergo a transformation in the presence of hexacarbonylmolybdenum and acid to yield functionalized thiazoles 3 in a one-pot reaction. In a few cases, 1,4,5-trisubstituted dihydroimidazoleth, iones 4 are also isolated as side products. Mechanistic considerations are outlined and scope and limitations of this new methodology discussed.