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Oxazolidine Formation, or Loss of Acid, from Attempted Fluorination of Amide Side-Chain in 2-Nitroimidazoles

TitleOxazolidine Formation, or Loss of Acid, from Attempted Fluorination of Amide Side-Chain in 2-Nitroimidazoles
Publication TypeJournal Article
Year of Publication2018
AuthorsBaird, IR, Patrick, BO, Skov, KA, James, BR
JournalJournal of Heterocyclic Chemistry
Volume55
Pagination1444-1449
Abstract

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.

URLhttps://onlinelibrary.wiley.com/doi/abs/10.1002/jhet.3183
DOI10.1002/jhet.3183