Nucleophilic displacement in 2-chloro(trifluoromethyl)pyridines with amines and ammonia
The activating effect of trifluoromethyl groups in 2-chloro(trifluoromethyl)pyridines was investigated by comparing reactions of these compounds and of 2-chloropyridine with secondary cyclic amines. The ammonolysis of 2-chloro-3-trifluoromethylpyridine and 2-chloro-4-trifluoromethylpyridine is also reported and shown to proceed, in contrast to the reported behaviour of 2-chloro-5-trifluoromethylpyridine, without hydrolysis of the trifluoromethyl function. Both 2-amino-3-trifluoromethylpyridine and 2-amino-4-trifluoromethylpyridine were converted (via the corresponding pyridones) to 3-trifluoromethylpyridin-2(1H)-thione and 4-trifluoromethylpyridin-2(1H)-thione, and a number of S-alkyl derivatives of the latter compounds were prepared.
Dunn
p. 153 - 157
(2007/10/03)
The Synthesis and Some Reactions of Novel Pyridine-2(1H)-thiones
The use of methyl 3-mercaptopropionate for the conversion of halogenated pyridins to pyridine thiones and thiols is described, and limitations of the reaction discussed.S-Alkylation and oxidation reactions of the products from these reactions are reported.
Dunn, A. D.,Norrie, R.,L'Hostis, J.,Marjot, S.
p. 119 - 125
(2007/10/02)
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