Rapid syntheses of nitroheterocycles that bear a diethyl methylenemalonate group ?β to a nitro group starting from easily available nitroheterocyclic sulfones and involving, a one-pot substitution-elimination with either diethyl bromomalonate or an original direct olefination with diethyl ketomalonate, gave moderate yields in nitroimidazole series. An SRN1 reaction followed by a base-mediated nitrous acid elimination gave fairly good yields in nitrothiazole series. Because of the accessibility of the reagents, these syntheses are interesting alternatives to Knoevenagel reaction.
Keywords: sulfonyl carbanion, julia olefination, desulfonylation, 5-nitroimidazole, 5-nitrothiazole
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