(E)-2-[2-(4-Chloromethylphenyl)vinyl]-1-methyl-5-nitro-1H-imidazole

Abstract

The title compound, (1), is a new reductive alkylating agent which is a convenient substrate for LD—SRN1 reactions with the anions of ethyl 2-nitropropionate and dialkyl α-substituted malonates. There is a strong conjugation between the different moieties constituting the skeleton of the molecule, as shown by the planarity of the structure: the angles between the planes C1—C2—C3—C4—C5—C6—C7—C8 and C5—C8—C9—C10, and the planes C9—C10—C11—N1—N2—N3—C13 and C5—C8—C9—C10 are 4.9 (5)° and 3.3 (5)° respectively. The planar nature of (1) led us to investigate its reactivity with other conventional nucleophiles. These electron-transfer C-alkylation reactions of (1) are the first examples of LD—SRN1 mechanism in 5-nitroimidazole series.