Premium
Nucleophilic substitution studies on nitroimidazoles, and applications to the synthesis of biologically active compounds
Author(s) -
Chauvière Gérard,
Viodé Cécile,
Périé Jacques
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370120
Subject(s) - chemistry , nucleophile , halogen , regioselectivity , imidazole , nucleophilic substitution , nitroimidazole , amine gas treating , trifluoromethyl , diazomethane , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , catalysis , alkyl
The rationalization of the synthesis of substituted analogs of megazol, a biologically active 5‐nitroimidazole at position 4 of the imidazole ring, had led to the study of intermediate steps. The methylation by diazomethane of 2,4‐(5)dihalogeno‐5‐(4)nitroimidazole is regioselective leading to 2,4‐dihalogeno‐1‐methyl‐5‐nitroimidazole 2. On this compound 2 , hard nucleophiles such as cyanide, methoxide or hydride anions react only with the halogen at the 2 position; whereas soft nucleophiles such as amine, thiol or trifluoromethyl anion from an organocopper species react only with the halogen at postion 4 in the intermediate 3b or compound 4b.