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Benzimidazole condensed ring systems, III . Synthesis of some substituted 2,3-dihydrocyclopenta-1H-[4′,5′: 2,3]pyrido[1,2-a]benzimidazole-11-carbonitriles

Kondensierte Ringsysteme des Benzimidazols, 3. Mitt.. Synthese von substituierten 2,3-Dihydrocyclopenta[4′,5′:2,3]pyrido[1,2-a]benzimidazol-11-carbonitrilen

  • Organische Chemie Und Biochemie
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Summary

The synthesis of compound3 by condensing 1H-benzimidazole-2-acetonitrile (1) with ethyl cyclopentanone-2-carboxylate (2) in the presence of ammonium acetate is described. Methylation of3 with trimethyl phosphate yielded the N-methyl derivative4. Methods for converting3 to some of its related derivatives in which the carbonyl function was replaced by Cl, N3 and amines are also reported.

Zusammenfassung

Die Synthese der tetracyclischen Verbindung3 durch Kondensation von 1H-Benzimidazol-2-acetonitril (1) mit Cyclopentanon-2-carbonsäureester (2) in Gegenwart von Ammonacetat wird beschrieben. Die Methylierung von3 mit Trimethylphosphat liefert das N-Methylderivat4. Die Sauerstoffunktion in3 kann durch Chlor, Azid und Aminogruppen ersetzt werden.

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References and Notes

  1. For Part 2 see: Rida S. M., Soliman F. S. G., Badawey E. A. M., Kappe T. (1988) J. Heterocycl. Chem. (in press); for Part 1 see Ref. [3]

  2. Soliman F. S. G., Rida S. M., Badawey E. A. M., Kappe T. (1984) Arch. Pharm.317: 914

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  3. Rida S. M., Soliman F. S. G., Badawey E. A. M., El-Ghazzawi E., Kader O., Kappe T. (1988) J. Heterocycl. Chem. (in press)

  4. Conducted at the National Cancer Institute, Bethesda, Maryland, USA

  5. Conducted in the Department of Microbiology, Medical Research Institute, University of Alexandria, A.R. Egypt

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Authors and Affiliations

  1. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, A. R. Egypt

    El-Sayed A. M. Badawey, Samia M. Rida & Farid S. G. Soliman

  2. Institute of Organic Chemistry, Karl-Franzens-University Graz, A-8010, Graz, Austria

    Thomas Kappe

Authors
  1. El-Sayed A. M. Badawey
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  2. Samia M. Rida
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  3. Farid S. G. Soliman
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  4. Thomas Kappe
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Badawey, ES.A.M., Rida, S.M., Soliman, F.S.G. et al. Benzimidazole condensed ring systems, III . Synthesis of some substituted 2,3-dihydrocyclopenta-1H-[4′,5′: 2,3]pyrido[1,2-a]benzimidazole-11-carbonitriles. Monatsh Chem 120, 73–76 (1989). https://doi.org/10.1007/BF00809651

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  • DOI: https://doi.org/10.1007/BF00809651

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