95633-73-1

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 4630-82-4 methyl cyclohexylcarboxylate 
• 68571-10-8 cyclohexyl(pyrrolidin-1-yl)methanone 
• 93031-47-1 2-(cyclohexylhydroxymethyl)-1-methyl-1H-imidazole 

Downstream Products

• 111930-99-5 2-(1-cyclohexyl-1-hydroxy-2-phenylethyl)-1-methyl-1H-imidazole 
• 93031-47-1 2-(cyclohexylhydroxymethyl)-1-methyl-1H-imidazole 
• 95633-78-6 n-propyl cyclohexanecarboxamide 
• 10035-86-6 S-ethyl cyclohexanecarbothioate 
• 111931-05-6 1,3-dimethyl-2-cyclohexyl-1-hydroxymethyl-1H-imidazolium iodide 
• 61259-29-8 1-cyclohexyl-2-phenylethanone 
• 118416-01-6 1-cyclohexyl-2-phenyl-1-oxo-2-butene 
• 118415-97-7 1-Cyclohexyl-2-phenyl-but-3-en-1-one 
• 16616-46-9 1-cyclohexyl-3-phenylprop-2-yn-1-one 
• 99802-99-0 2-cyclohexylcarbonyl-1,3-dimethyl-1H-imidazolium monomethyl sulphate 

Relevant academic research and scientific papers

PREPARATION OF SYNTHETICALLY USEFUL 2-ACYL-1H-IMIDAZOLES BY AN AUTOOXIDATION OF 1H-IMIDAZOLYL-2-METHANOL DERIVATIVES

1-Methyl-1H-imidazolyl-2-methanol derivatives (4) were autooxidized in a reaction medium consisting of air, sodium hydride, pyrazole and tetrahydrofuran to give the corresponding 2-acyl-1-methyl-1H-imidazoles (1) in good yields.

Synthesis and Application of Imidazole Derivatives. Synthesis and Acyl Activation of 2-Acyl-1-methyl-1H-imidazoles

2-Acyl-1-methyl-1H-imidazoles (3) were prepared in good yields by treating 1-acylpyrrolidines (5) with 2-lithio-1-methyl-1H-imidazole (2) at -78 deg C.The acyl group of 3 was very stable under various severe conditions, but 2-benzoylimidazole (3a) was gradually hydrolyzed by heating with 1.3 N NaOH to produce benzoic acid and 1-methyl-1H-imidazole.Acyl activation of 3 was performed by direct quaternization of 3 with iodomethane or dimethyl sulfate or more successfully by quaternization of the corresponding O-trimethylsilylated gem-cyanohydrin (11) with dimethyl sulfate.Keywords- acylimidazole; 2-acylimidazole; imidazolium salt; acyl group activation; acylation; C-C bond fission; protecting group; latent functionality

SYNTHESIS OF 2-ACYL-1-METHYL-1H-IMIDAZOLES AND REACTIVITY OF THE ACYL GROUP

2-Alkanoyl- and 2-aroyl-1-methyl-1H-imidazoles (3) were prepared in good yields by treating 1-acylpyrrolidine (1) with 2-lithio-1-methyl-1H-imidazole (2) at -78 deg C.Although 2-benzoyl-1-methyl-1H-imidazole (3a) was stable under n-Pr-NH2/80 deg C/10 h; 2percent K2CO3/aq.CH3OH/80 deg C/10 h; 20percent H2SO4/80 deg C/10 h; CF3COOH/r.t./17 h, it was hydrolysed into benzoic acid and 1-methyl-1H-imidazole by heating in 1.3 N-NaOH - aq. ethanol at 80 deg C for 30 h.The acyl group of 3 was activated by conversion to the corresponding imidazolium salt (4), which could react with various nucleophiles.