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An N → N′-benzyl migration during the formation of some (trifluoro-methyl)imidazo[4,5-h]quinolines

Authors
Journal
Journal of Fluorine Chemistry
0022-1139
Publisher
Elsevier
Publication Date
Volume
41
Issue
2
Identifiers
DOI: 10.1016/s0022-1139(00)81550-x

Abstract

Abstract Photolysis of 8-azidoquinoline in dioxan-benzylamine followed by cyclisation of the resulting 7-amino-8-benzylaminoquinoline (1a) in hot trifluoroacetic acid gave a mixture of isomeric 2-(trifluoromethyl)imidazoquinolines. The structures of these isomers have been established by spectroscopic data and by alternative synthesis from unambiguously prepared 7-amino-8-benzyl-amino-(1a) and from 8-amino-7-benzylamino-quinoline (4c) respectively, as the expected 1-benzyl-2-(trifluoromethyl)imidazo[4,5- h ]quinoline (2a) (6%) and the expected and rearranged 1-benzyl-2-(trifluoromethyl)imidazo[5,4- h ]quinoline (3a) (52%). Examples of this N → N′ alkyl rearrangement in the presence of acetic and formic acid, and with other alkylamino-groups are noted.

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