79713-57-8

Upstream product

• 215675-49-3 1-cyclohexyl-4,5-diphenylimidazole 3-oxide 
• 1266332-43-7 C₃H₂F₆O₂*C₂₁H₂₂N₂O 
• 574-15-2 benzilmonoxime 
• 6281-14-7 1,3,5-tricyclohexyl-[1,3,5]triazinane 
• 5014-83-5 4,5-diphenyloxazol-2-one 
• 108-91-8 cyclohexylamine 

Relevant academic research and scientific papers

First synthesis of the N(1)-bulky substituted imidazole 3-oxides and their complexation with hexafluoroacetone hydrate

Synthesis of new 2-unsubstituted imidazole 3-oxides bearing bulky substituents at the N(1) atom, based on the condensation of appropriate alkylamines, formaldehyde, and corresponding a-(hydroxyimino)ketone, is described. Treatment of imidazole 3-oxides with hexafluoroacetone hydrate (HFAH) yields crystalline 1:1 complexes in nearly quantitative yields. Heating of isolated complexes possessing phenyl ring at the C(4) atom of imidazole ring, results in their isomerization into imidazol-2-ones in fair yields. The formation of analogous complexes of HFAH with other azole N-oxides is also described. ARKAT-USA, Inc.

Reactions of 2-unsubstituted 1H-imidazole 3-oxides with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile: A stepwise 1,3-dipolar cycloaddition

The reaction of 1,4,5-trisubstituted 1H-imidazole-3-oxides 1 with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile (7, BTF) yielded the corresponding 1,3-dihydro-2H-imidazol-2-ones 10 and 2-(1,3-dihydro-2H-imidazol- 2-vlidene)malononitriles 11, respectiv

Synthesis of imidazole derivatives using 2-unsubstituted 1H-imidazole 3- oxides

The reaction of 1,4,5-trisubstituted 1H-imidazole 3-oxides 1 with Ac2O in CH2Cl2 at 0-5°leads to the corresponding 1,3-dihydro-2H-imidazol-2-ones 4 in good yields. In refluxing Ac2O, the N-oxides 1 are transformed to N- acetylated 1,3-dihydro-2H-imidazol-2-ones 5. The proposed mechanisms for these reactions are analogous to those for N-oxides of 6-membered heterocycles (Scheme2). A smooth synthesis of 1H-imidazole-2-carbonitriles 2 starting with 1 is achieved by treatment with trimethylsilanecarbonitrile (Me3SiCN) in CH2Cl2 at 0-5°(Scheme 3).

RECYCLIZATION OF 4,5-DIPHENYLOXAZOLIN-2-ONE AND -2-THIONE UNDER THE INFLUENCE OF AMINES

4,5-Diphenyl-4-oxazolin-2-one and -2-thione undegro recyclization to 1-substituted 4,5-diphenyl-4-imidazolin-2-ones and -2-thiones, respectively, under the influence of primary amines.The action of hydrazine hydrate on the oxazolone leads to 5,6-diphenyl-1,2,3,4,-tetrahydro-1,2,4-triazin-3-one.The corresponding ureas were isolated from the reaction mixtures in a number of cases.