2024-03-29T13:42:36Z
https://niigata-u.repo.nii.ac.jp/oai
oai:niigata-u.repo.nii.ac.jp:00001694
2022-12-15T03:34:24Z
176:488:489
453:454
AN EFFECTIVE PROCEDURE TO PROMOTE AZA-PRINS CYCLIZATION REACTIONS EMPLOYING A COMBINATION OF FERRIC CHLORIDE AND AN IMIDAZOLIUM SALT IN BENZOTRIFLUORIDE
Osawa, Chika
Tateyama, Minami
Miura, Kensuke
Tayama, Eiji
Iwamoto, Hajime
Hasegawa, Eietsu
Copyright(C)2012 Japan Institute of Heterocyclic Chemistry
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.
Elsevier
2012-12
eng
journal article
http://hdl.handle.net/10191/31007
https://niigata-u.repo.nii.ac.jp/records/1694
info:doi/10.3987/COM-12-S(N)78
AA00663739
03855414
Heterocycles
Heterocycles
86
2
1211
1226
https://niigata-u.repo.nii.ac.jp/record/1694/files/86_2_1211-1226.pdf
application/pdf
496.6 kB
2019-07-29