Transformations of the imidazole ring in 1-alkyl- and 1-aryl-4-nitroimidazoles following the attack of hydroxylamine or 4-amino-1,2,4-triazole
Novel imidazole-oxadiazole ring interconversions (transformations) accompanying nucleophilic amination of 4-nitroimidazoles by hydroxylamine or 4-amino-1,2,4-triazole are described with suggestions concerning mechanisms of the reactions. 1996 Plenum Publishing Corporation.
Nitroimidazoles XVII. Nucleophilic Amination or Ring Transformation in Reactions of 1-Aryl-4-nitroimidazoles with 4-Amino-1,2,4-triazole or Hydroxylamine
1-Aryl-4-nitroimidazoles under action of 4-amino-1,2,4-triazole in the presence of MeONa in DMSO undergo a vicarious nucleophilic substitution of hydrogen to give 5-amino-1-aryl-4-nitroimidazoles.If reacted with hydroxylamine in the presence of KOH or MeO
Suwinski, Jerzy,Swierczek, Krzysztof,Glowiak, Tadeusz
RING TRANSFORMATION REACTIONS IN 4-NITROIMIDAZOLES FOLLOWING AN ATTACK OF NUCLEOPHILES
It was proved that 4-nitroimidazoles substituted at the nitrogen atom 1 with electron acceptor groups (aryl, arenesulfonyl, nitro) in reactions with some nucleophiles yield the products of ordinary or degenerated imidazole ring transformation (oxadiazoles, triazoles, imidazoles).
Suwinski, Jerzy,Pawlus, Wojciech,Salwinska, Ewa,Swierczek, Krzysztof
p. 1511 - 1520
(2007/10/02)
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