Rapid Syntheses of Nitroheterocycles that Bear a Diethyl Methylenemalonate Group β to a Nitro Group

Title: Rapid Syntheses of Nitroheterocycles that Bear a Diethyl Methylenemalonate Group β to a Nitro Group

Volume: 1 Issue: 4

Author(s): Maxime D. Crozet, Patricia Perfetti, Mustapha Kaafarani, Michel P. Crozet and Patrice Vanelle

Affiliation:

Keywords: sulfonyl carbanion, julia olefination, desulfonylation, 5-nitroimidazole, 5-nitrothiazole

Abstract: 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.

Cite this article as:

Crozet D. Maxime, Perfetti Patricia, Kaafarani Mustapha, Crozet P. Michel and Vanelle Patrice, Rapid Syntheses of Nitroheterocycles that Bear a Diethyl Methylenemalonate Group β to a Nitro Group, Letters in Organic Chemistry 2004; 1 (4) . https://dx.doi.org/10.2174/1570178043400488