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A facile synthesis of novel pyridone-annelated spirooxindolepyrrolidines via 1,3-dipolar cycloaddition

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Abstract

A series of novel pyridine-annelated spirooxindole-3,2′-pyrrolidines was prepared via 1,3-cycloaddition reaction involving N-methylmaleimide as 1,3-dipolarophile and the appropriate azomethine ylide. The latter 1,3-dipolar species were generated in situ via decarboxylative condensation reaction of the particular α-amino acid with pyridine-annelated isatin in aqueous methanol under reflux. The structures of these new spirooxindole cycloadducts are based on microanalytical, spectral (IR, HRMS, and NMR), and X-ray crystal data.

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Acknowledgments

This research work has been supported financially by the Scientific Research Support Fund (SRSF/project number-mph/1/6/2011) at Amman, Jordan.

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Authors and Affiliations

  1. Chemistry Department, Faculty of Science, The University of Jordan, Amman, 11942, Jordan

    Randa M. Al-As’ad, Mustafa M. El-Abadelah, Salim S. Sabri, Jalal A. Zahra & Firas F. Awwadi

  2. Interfakultäres Institut für Biochemie, Universität Tübingen, Hoppe-Seyler-Straße 4, 72076, Tübingen, Germany

    Wolfgang Voelter

Authors
  1. Randa M. Al-As’ad
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  2. Mustafa M. El-Abadelah
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  3. Salim S. Sabri
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  4. Jalal A. Zahra
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  5. Firas F. Awwadi
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  6. Wolfgang Voelter
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Corresponding authors

Correspondence to Mustafa M. El-Abadelah or Wolfgang Voelter.

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Al-As’ad, R.M., El-Abadelah, M.M., Sabri, S.S. et al. A facile synthesis of novel pyridone-annelated spirooxindolepyrrolidines via 1,3-dipolar cycloaddition. Monatsh Chem 146, 621–629 (2015). https://doi.org/10.1007/s00706-014-1391-6

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  • DOI: https://doi.org/10.1007/s00706-014-1391-6

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