@article {31304,
	title = {Oxazolidine Formation, or Loss of Acid, from Attempted Fluorination of Amide Side-Chain in 2-Nitroimidazoles},
	journal = {Journal of Heterocyclic Chemistry},
	volume = {55},
	year = {2018},
	pages = {1444-1449},
	abstract = {<p>Reaction of Etanidazole (a 2-nitroimidazole derivative with an amide side-chain containing a hydroxyethyl group) with triflic anhydride gives, depending on conditions, a trifluoromethyl(sulfonyl)oxazolidine via a cyclization reaction, or a fluorine-free formate derivative; reaction with tosyl chloride gives only a chloroethyl derivative. An attempt to replace a Br-atom in a related propyl-containing amide side-chain by a F-atom forms instead a propylene derivative via loss of HBr. The studies stem from interest in use of 2-nitroimidazoles with fluorine-containing amide side-chains as hypoxia markers.</p>},
	doi = {10.1002/jhet.3183},
	url = {https://onlinelibrary.wiley.com/doi/abs/10.1002/jhet.3183},
	author = {Baird, Ian R. and Patrick, Brian O. and Skov, Kirsten A. and James, Brian R.}
}
