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An efficient method for the synthesis of spiro and fused N-heterocyclic phosphor esters. Reactions of triketoindan-2-oxime with α-phosphonyl carbanions

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Abstract

Treatment of triketoindan-2-oxime with α-phosphonyl carbanions in sodium ethanolate solution at reflux temperature led to a number of the corresponding substituted spiroisooxazole-, fused 1,3-oxazole, and 1,4-oxazine phosphor esters in moderate to high yields. Mechanisms for the formation of five- and six-membered rings are provided. A comparison of Wittig-Horner and Wittig reagent counterparts in reactions with the oxime is discussed. The various biological properties of selected examples of the synthesized products were studied.

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Authors and Affiliations

  1. Chemical Industries Division, National Research Center, Cairo, Egypt

    Wafaa M. Abdou, Ashraf A. Sediek & Maha D. Khidre

Authors
  1. Wafaa M. Abdou
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  2. Ashraf A. Sediek
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  3. Maha D. Khidre
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Corresponding author

Correspondence to Wafaa M. Abdou.

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Correspondence: Wafaa M. Abdou, Chemical Industries Division, National Research Center, Elbohouth St., D-12622 Dokki, Cairo, Egypt.

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Abdou, W., Sediek, A. & Khidre, M. An efficient method for the synthesis of spiro and fused N-heterocyclic phosphor esters. Reactions of triketoindan-2-oxime with α-phosphonyl carbanions. Monatsh Chem 139, 617–623 (2008). https://doi.org/10.1007/s00706-007-0806-z

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  • DOI: https://doi.org/10.1007/s00706-007-0806-z

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