Heterocycles p. 1211 - 1226 (2012)
Update date:2022-08-03
Topics:
Osawa, Chika
Tateyama, Minami
Miura, Kensuke
Tayama, Eiji
Iwamoto, Hajime
Hasegawa, Eietsu
Aza-Prins cyclization reactions of N-tosyl-3-butenylamine with p-methoxybenzaldehyde, 1-naphthaldehyde and 2-naphthaldehyde take place efficiently using a combination of ferric chloride and 1-butyl-3- methylimidazolium hexafluorophosphate in benzotrifluoride (FeIm-BTF procedure). The new methodology, leading to formation of target N-tosyl-4-chloro-2- substituted piperidines, is superior to the one using 1-butyl-3- methylimidazolium tetrachloroferrate. The FeIm-BTF procedure was also applied to aza-Prins cyclization reactions of other aldehydes. Finally, the effects of imidazolium salts on aza-Prins cyclization reaction promoted by boranetrifluoride-diethyl ether complex, leading to formation of fluorinated piperidines, were explored.
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