Fluorocarbon derivatives of nitrogen. Part 11. Synthesis of some 2-(trifluoromethyl)imidazo[1,2-]pyridines from trifluoroacetonitrile |
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Authors: | Ronald Eric Banks Julie Thomson |
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Affiliation: | Chemistry Department, The University of Manchester Institute of Science and Technology, Manchester M60 1QD U.K. |
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Abstract: | 3-(t-Butoxycarbonyl)-2-(trifluoromethyl)imidazo[1,2-]-pyridine, prepared from trifluoroacetonitrile and pyridinium t-butoxycarbonylmethylide, reacts smoothly with trifluoroacetic acid to provide 2-(trifluoromethyl)imidazo[1,2-]pyridine-3-carboxylic acid, which gives 2-(trifluoromethyl)imidazo[1,2-]-pyridine when heated. 3-Cyano-2-(trifluoromethyl)imidazo[1,2-]pyridine can be obtained treatment of trifluoroacetonitrile with pyridinium cyanomethylide, which is sufficiently reactive to effect nucleophilic displacement of fluorine from pentafluoropyridine under mild conditions [→pyridinium cyano(tetrafluoro-4-pyridyl)methylide]. |
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Keywords: | To whom enquiries should be addressed. |
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