66696-93-3Relevant academic research and scientific papers
Synthesis of cyclic hemiketals and spiroketals from dioxanorbornanes
Winkler, Jeffrey D.,Mikochik, Peter J.
, p. 3735 - 3737 (2007/10/03)
(Chemical Equation Presented) A new method for the synthesis of substituted pyranone hemiketals from dioxanorbornanes via Sml2 is described. Also reported is a synthesis of spiro[4.5]ketals from analogous intermediates via acid-promoted deprote
Synthesis and Application of Imidazole Derivatives. Synthesis and Acyl Activation of 2-Acyl-1-methyl-1H-imidazoles
Ohta, Shunsaku,Hayakawa, Satoshi,Moriwaki, Hiroki,Harada, Suzumi,Okamoto, Masao
, p. 4916 - 4926 (2007/10/02)
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
GENERATION OF AN ACTIVE ACYL SPECIES FROM STABLE 1-METHYL-2-ACYL-1H-IMIDAZOLES
Ohta, Shunsaku,Hayakawa, Satoshi,Okamoto, Masao
, p. 5681 - 5684 (2007/10/02)
1-Methyl-2-(1'-cyano-1'-trimethylsilyloxy)alkyl-1H-imidazoles (2) were easily prepared from the corresponding stable carbonyl compounds, 1-methyl-2-acyl-1H-imidazoles (1).When the quarternary salts of 2 were treated with various nucleophiles, reactive acyl species, which was presumed to be acylcyanide (12), was generated in situ under C-C bond fission to result in producing the corresponding acylated compounds (5-10) in good yields.
