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Synthesis and crystal structure of some 3,5-pyrazolidinediones

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Chemistry of Heterocyclic Compounds Aims and scope

Syntheses of various derivatives of 3,5-pyrazolidenedione are reported. This includes 4-arylidene (alkylidene or aralkylidene)-3,5-pyrazolidinediones, which on epoxidation gave unreported oxiranes. The syntheses of these derivatives were based on either the Knoevenagel reaction of carbonyl derivatives with 3,4-pyrazolidinedione or cyclization of arylidene (alkylidene) malonic acid hydrazide with glacial acetic acid. 4-Arylazo-3,5-pyrazolidinedione derivatives were also prepared by coupling of aryldiazonium salts with 3,5-pyrazolidinedione or cyclization of arylazomalonic acid hydrazide. Reduction of 4-benzylidene derivatives gave the corresponding benzyl derivatives. The structure of the new products was confirmed by elemental and spectral analyses and X-ray crystallography.

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Authors and Affiliations

  1. Chemistry Department, Assiut University, Assiut, Egypt

    Saoud A. M. Metwally, Maisa I. Abdel Moneim & Yasser A. Elossely

  2. Forensic Medicine Laboratories, Assiut, Egypt

    Radwa I. Awad

  3. Institute of Organic Chemistry, University of Zurich, Zurich, Switzerland

    Khaled Abou-Hadeed

Authors
  1. Saoud A. M. Metwally
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  2. Maisa I. Abdel Moneim
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  3. Yasser A. Elossely
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  4. Radwa I. Awad
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  5. Khaled Abou-Hadeed
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Correspondence to Saoud A. M. Metwally.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 538-550, April 2010.

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Metwally, S.A.M., Abdel Moneim, M.I., Elossely, Y.A. et al. Synthesis and crystal structure of some 3,5-pyrazolidinediones. Chem Heterocycl Comp 46, 426–437 (2010). https://doi.org/10.1007/s10593-010-0527-9

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  • DOI: https://doi.org/10.1007/s10593-010-0527-9

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