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Russian Journal of General Chemistry

, Volume 87, Issue 6, pp 1246–1255 | Cite as

Synthesis and antimicrobial activity of novel fused [1,2,4]triazino[5,6-b]indole derivatives

  • A. G. Al Osaimi
  • R. S. AliEmail author
  • H. A. Saad
  • M. R. El Sayed Aly
Article

Abstract

Synthesis of new fused systems of triazino[5,6-b]indole starting with preparation of 3-amino[1,2,4]-triazino[5,6-b]indole 1 by reaction of isatin with 2-aminoguanidinium carbonate in boiling acetic acid is presented [1]. Intermediate compound 1 reacted with aldehyde, ethyl chloroformate, triethyl orthoformate, and ninhydrine and gave new heterotetracyclic nitrogen systems, such as 3-(N 2-guanidinylimino)indole-2(1H)-one 2, 3-(N-ethoxycarbonylamino)-4H-[1,2,4]triazino[5,6-b]indole 3, 3-(N-ethoxymethyleneamino)-4H-[1,2,4]-triazino[5,6-b]indole 4, 3-(hydrazinothiocarbonylamino)-4H-[1,2,4]triazino[5,6-b]indole 5, respectively. N-(1,3-dioxoindene-2-ylidene)-4H-[1,2,4]triazino[5,6-b]indol-3-amine 6 was synthesized by reaction of compound 1 with aldehyde, ethyl chloroformate, triethyl orthoformate, and ninhydrine. New fused indole systems, pyrimido[2′,1′:3,4][1,2,4]triazino[5,6-b]indol-3(4H)-one 8, 9, 11, 12 and 1H-imidazo[2′,1′:3,4][1,2,4]triazino-[5,6-b]indol-2(3H)-one 10, were synthesized in the reaction of the intermediate 1 with bifunctional compounds. Structures of the products were elucidated from their elemental analysis and spectral data (IR, 1H and 13C NMR and mass spectra). Antimicrobial activity of some synthesized compounds was tested.

Keywords

imidazo[2′,1′:3,4][1,2,4]triazino[5,6-b]indole [1,2,4]triazino[5,6-b]indol-3-amine pyrimido[2′,1′:3,4]-[1,2,4]triazino[5,6-b]indole biological activity 

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Copyright information

© Pleiades Publishing, Ltd. 2017

Authors and Affiliations

  • A. G. Al Osaimi
    • 1
  • R. S. Ali
    • 1
    • 2
    Email author
  • H. A. Saad
    • 1
    • 3
  • M. R. El Sayed Aly
    • 1
    • 4
  1. 1.Chemistry Department, Faculty of ScienceTaif UniversityTaifKingdom of Saudi Arabia
  2. 2.Department of Basic ScienceFaculty of Industrial Education, Helwan UniversityCairoEgypt
  3. 3.Chemistry Department, Faculty of ScienceZagazig UniversityZagazigEgypt
  4. 4.Chemistry Department, Faculty of Applied SciencePort Said UniversityPort SaidEgypt

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