Synthese et Reactions SRN1 en Serie 3-Nitroimidazopyrimidine

Article abstract of DOI:10.1016/0040-4020(95)00539-K

A new heterocyclic reductive alkylating agent, 2-chloromethyl-3-nitroimidazo<1,2-a>pyrimidine, is synthesized for the first time and shown to react under phase-transfer catalysis conditions with 2-nitropropane anion to give good yield of the C-alkylated derivative.Elimination of nitrous acid allows to obtain a new class of imidazo<1,2-a>pyrimidine derivatives bearing a trisubstituted ethylenic bond in the 2 position.The S_RN1 mechanism of C-alkylation is confirmed by classical inhibition experiments by dioxygen, p-dinitrobenzene or TEMPO.