Title: Molecular-rearrangements of 4-iminomethyl-1,2,3-triazoles - replacement of 1-aryl substituents in 1h-1,2,3-triazole-4-carbaldehydes
Authors: Labbe, G ×
Bruynseels, M
Delbeke, P
Toppet, Suzanne #
Issue Date: Jan-1990
Publisher: Hetero corporation
Series Title: Journal of heterocyclic chemistry vol:27 issue:7 pages:2021-2027
Abstract: The two structural isomers, 4 and 5, of 1-substituted-4-iminomethyl-1,2,3-triazoles are interconvertible when heated in dimethyl sulfoxide at 80-degrees. The equilibrium position depends on the electronic properties of the R-substituent, favoring 5 for R = alkyl, benzyl and anisyl, and 4 for p-chlorophenyl and p-nitrophenyl. An interesting application is the synthesis of 1-alkyl-1,2,3-triazole-4-carbaldehydes from 1-phenyl-1,2,3-triazole-4-carbaldehyde by Scheme I. The hydrazones 4ij and the oxime 4k do not rearrange due to an unfavorable Z-configuration around the C = N bond, whereas the acyloximino derivative 4m is converted into the nitrile 11. The structures of the products have been fully characterized by C-13 nmr spectroscopy and the mechanistic details of the rearrangement are discussed.
ISSN: 0022-152X
Publication status: published
KU Leuven publication type: IT
Appears in Collections:Molecular Design and Synthesis
× corresponding author
# (joint) last author

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