99802-92-3

Upstream product

• 616-47-7 1-methyl-1H-imidazole 
• 99802-88-7 4-hydroxy-4-phenyl-1-(pyrrolidine-1-yl)butan-1-one 
• 2051-95-8 succinylbenzene 
• 53917-82-1 β-benzoylpropionyl chloride 
• 51459-75-7 1-phenyl-4-(pyrrolidine-1-yl) butane-1,4-dione 

Relevant academic research and scientific papers

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.