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

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

Journal Name: Letters in Organic Chemistry

Volume 1 , Issue 4 , 2004

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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.

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

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Article Details

VOLUME: 1
ISSUE: 4
Year: 2004
Page: [326 - 330]
Pages: 5
DOI: 10.2174/1570178043400488
Price: $58

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