Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 2103–2111 | Cite as

Design and synthesis of new functionalized isoindigo and (3Z,3′Z)-3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) derivatives

  • Gholamhossein KhaliliEmail author
  • Anthony C. Willis
  • Paul A. Keller
Original Paper


A library of N,N-substituted isoindigo derivatives were prepared by reaction of isoindigo with a variety of alkylating agents in the presence of MeONa under mild conditions in yields of 65–80%. A new, more efficient synthesis of (3Z,3′Z)-3,3′-(ethane-1,2-diylidene)bis(indolin-2-one) is described by reaction of oxindole with glyoxal at reflux in methanol—a small library of N,N′-substituted derivatives were also prepared in 60–70% yield.

Graphical abstract


Isoindigo Oxindole (3Z,3′Z)-3,3′-(Ethane-1,2-diylidene)bis(indolin-2-one) 



We thank the Centre for Molecular Biosciences at the University of Wollongong for support.

Supplementary material

706_2018_2272_MOESM1_ESM.pdf (1.3 mb)
Supplementary material 1 (PDF 1327 kb)


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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Gholamhossein Khalili
    • 1
    • 2
    Email author
  • Anthony C. Willis
    • 3
  • Paul A. Keller
    • 1
  1. 1.School of ChemistryUniversity of WollongongWollongongAustralia
  2. 2.Chemistry DepartmentBushehr Branch, Islamic Azad UniversityBushehrIran
  3. 3.Research School of ChemistryAustralian National UniversityCanberraAustralia

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