Molecular rearrangements of 4??iminomethyl??1, 2, 3??triazoles. Replacement of 1??aryl substituents in 1H??1, 2, 3??triazole??4??carbaldehydes

G L'abbé, M Bruynseels, P Delbeke…

Index: L'abbe, Gerrit; Bruynseels, Maria; Delbeke, Pieter; Toppet, Suzanne Journal of Heterocyclic Chemistry, 1990 , vol. 27, # 7 p. 2021 - 2027

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Citation Number: 22

Abstract

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. 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 ...