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Fluorinated pyridine derivatives: Part 1. The synthesis of some mono- and bis-quaternary pyridine salts of potential use in the treatment of nerve agent poisoning

ISSN:0022-1139
2005年第126卷第8期
Christopher M. Timperley:cmtimperley@dstl.gov.uk,Mike Bird,Suzannah C. Heard,Stuart Notman,Robert W. Read,John E.H. Tattersall,Simon R. Turner

Experiments were performed to determine whether F- and CF3-substituted pyridines undergo quaternization with iodomethane (1:1 molar ratio in THF) and 1,3-diiodopropane (2:1 molar ratio in MeCN). 2-Fluoropyridine and 2-(trifluoromethyl)pyridine did not react with MeI even under prolonged reflux, while 3-fluoropyridine, 3,5-difluoropyridine, 3-(trifluoromethyl)pyridine and 4-(trifluoromethyl)pyridine gave methiodide salts in 28-72% yield. 2-Fluoropyridine did not react with I(CH2)3I, 3-fluoropyridine gave the bis-quaternary salt and 3,5-difluoropyridine yielded a mono-quaternary derivative. Both 3- and 4-(trifluoromethyl)pyridine furnished the bis-quaternary products in 53 and 55% yield, respectively. The bis-quaternary salts are potentially useful in the treatment of organophosphorus nerve agent poisoning.

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ISSN:0022-1139
2005年第126卷第8期

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