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Photochemical tri fluoro methylation of some biologically significant imidazoles/

, : Photochemical tri fluoro methylation of some biologically significant imidazoles/. Journal of Organic Chemistry 49(6): 1060-1064

The trifluoromethyl radical, generated by UV irradiation of trifluoromethyl iodide in methanol solution, reacts with N-acylhistamines and N-acylhistidine esters to effect ring substitution at C-2 (13-27% yield) and at C-4 (23-34% yield). Small amounts of the 2,4-bis products are also obtained. 2-(4-Methoxyphenyl)imidazole is substituted selectively on imidazole in 55% yield and 2-(4-pyridyl)imidazole in 28% yield. Phototrifluoromethylation of methyl trans-urocanate provides low yields of the 4-CF3 cis and 4-CF3 trans ester, as well as products resulting from substitution and addition at the olefinic double bond.

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Related references

Kimoto H.; Fujii S.; Cohen L.A., 1982: Photochemical per fluoro alkylation of imidazoles. Imidazole and its derivatives undergo facile trifluoromethylation or perfluoroalkylation, in methanol solution at ambient temperature, following radical dissociation of RFI [fluoroalkyl imidazole] by .gamma. or UV irradiation. In the case of imida...

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