Journal of Surfactants and Detergents

, Volume 17, Issue 1, pp 101–109 | Cite as

Synthesis, Autoorganization and Reactivity of Amphiphilic Derivatives of 1-Aminoisoindole in Water and Formamide

  • Igor V. Levkov
  • Stephanie Cassel
  • Zoia V. Voitenko
  • Nathalie Saffon
  • Armand Lattes
  • Isabelle Rico-Lattes
Original Article


In this work, we present the synthesis of cationic surfactants based on 1-aminoisoindole. The physico-chemical properties were studied by conductometry, tensiometry, dynamic light scattering and transmission electron microscopy in water and in formamide. The reactivity of these novel surfactants has been studied at concentrations below and above critical aggregation concentrations (CAC) and it was found that reactions can proceed in structured media without the addition of other catalysts.


Isoindole Surfactant Micelle Cycloaddition 



The present researches were carried out in the context of IRG “Franco-Ukrainian Collaboration in Molecular Chemistry”. This work was supported by the CNRS (16 Avenue Edouard Belin, 31055 Toulouse Cedex 4, France).


  1. 1.
    Toja E, Omodei-Sale A, Favara D, Cattaneo C, Gallico L, Galliani G (1983) Synthesis and pregnancy terminating activity of 2-arylimidazo[2,1-a]isoquinolines and isoindoles. Arzneim-Forsch 33:1222–1225Google Scholar
  2. 2.
    Lerner LJ (1989) Development of novel embryotoxic compounds for interceptive fertility control in the dog. J Reprod Fertil Suppl 39:251–265Google Scholar
  3. 3.
    Bonnett R, North SA (1981) The chemistry of the isoindoles. Adv Heterocycl Chem 29:341–399Google Scholar
  4. 4.
    Kreher R, Herd K-J (1982) Tricyclische 2H-isoindole Reaktionspartner fur CC- und NN-Dienophile. Chem–Ztg 106:305–308Google Scholar
  5. 5.
    Kreher RP, Kohl N (1984) An economical preparation method for 2H-isoindoles. Angew Chem 96:507–508CrossRefGoogle Scholar
  6. 6.
    Kreher RP, Use G (1988) Reactions of 2H-isoindole with maleic imides: a simple procedure for the preparation of 7-azabicyclo[2.2.1]heptanes. Chem Ber 121:927–934CrossRefGoogle Scholar
  7. 7.
    Bonnett R, North SA, Newton RF, Scopes DI (1983) Substitution and addition reactions of isoindoles. Tetrahedron 39:1401–1405CrossRefGoogle Scholar
  8. 8.
    Kovtunenko VA, Voitenko ZV (1994) The chemistry of isoindoles. Russ Chem Rev 63:997–1018CrossRefGoogle Scholar
  9. 9.
    Kreher RP, Feldhoff U, Seubert J, Schmitt D (1987) Isoindoles and isoindolenines. Part 25. 2-Aryl-2H-isoindoles. Chem–Ztg 111:155–169Google Scholar
  10. 10.
    Orti E, Bredas JL (1988) Electronic structure of metal-free phthalocyanine: a valence effective Hamiltonian theoretical study. J Chem Phys 89:1009–1017CrossRefGoogle Scholar
  11. 11.
    Kreher RP, Seubert J, Schmitt D, Use G, Kohl N, Muleta T (1990) Untersuchungen zur chemie von isoindolen und isoindoleninen, 36. Untersuchungen zur Chemie von Isoindolen und Isoindoleninen, 36. Reaktionen von 2-Alkyl-2H-isoindolen mit Maleinimiden. Chem Ber 123:381–390CrossRefGoogle Scholar
  12. 12.
    Zhou Z, Parr RG (1989) New measures of aromaticity: absolute hardness and relative hardness. J Am Chem Soc 111:7371–7379CrossRefGoogle Scholar
  13. 13.
    Troll T, Ollmann GW (1981) Preparation and reactions of l,3-bis-(trimethylsilyloxy)-isobenzofurans and –isoindoles. Tetrahedron Lett 22:3497–3500CrossRefGoogle Scholar
  14. 14.
    Pokholenko AA, Voitenko ZV, Kovtunenko VA (2004) Pyrido- and pyrimidoisoindoles: methods of synthesis and properties. Russ Chem Rev 73:771–784CrossRefGoogle Scholar
  15. 15.
    Veber DF, Lwowski W (1963) 1-arylisoindoles. J Am Chem Soc 85:646–647CrossRefGoogle Scholar
  16. 16.
    Levkov IV, Turov OV, Shishkin OV, Shishkina SV, Voitenko ZV (2010) The Curtin-Hammett principle in action: 1-amino-3H-isoindole in cycloaddition reactions. Tetrahedron 66:508–512CrossRefGoogle Scholar
  17. 17.
    Grieco PA (1998) Organic synthesis in water. Blackie Academic, New YorkCrossRefGoogle Scholar
  18. 18.
    Otto S, Engberts JBFN (2000) Diels–Alder reactions in water. Pure Appl Chem 72:1365–1372CrossRefGoogle Scholar
  19. 19.
    Otto S, Engberts JBFN (2001) In reactions and synthesis in Micellar media. Marcel Dekker, New York, pp 247–263Google Scholar
  20. 20.
    Theo R, Engberts JBFN (2002) Micellar catalysis of Diels–Alder reactions: substrate positioning in the micelle. J Org Chem 67:7369–7377CrossRefGoogle Scholar
  21. 21.
    Lattes A, Perez E, Rico-Lattes I (2009) Organized molecular systems in structured non aqueous solvents. Is formamide a water like solvent? CR Chimie 12:45–53CrossRefGoogle Scholar
  22. 22.
    SAINT-NT (2000) Bruker AXS Inc.: Madison, WisconsinGoogle Scholar
  23. 23.
    SADABS, Program for data correction, Bruker − AXSGoogle Scholar
  24. 24.
    Sheldrick GM (2008) A short history of SHELX. Acta Crystallog Sect A 64:112–122CrossRefGoogle Scholar
  25. 25.
    Levkov IV, Voitenko ZV, Zaporozhets OA, Linnik RP, Shishkina SV, Shishkin OV (2011) Synthesis and fluorescence properties of 4-aminobenzo[f]isoindole derivatives. J Chem Res 35:209–213CrossRefGoogle Scholar

Copyright information

© AOCS 2013

Authors and Affiliations

  • Igor V. Levkov
    • 1
    • 3
  • Stephanie Cassel
    • 1
  • Zoia V. Voitenko
    • 3
  • Nathalie Saffon
    • 2
  • Armand Lattes
    • 1
  • Isabelle Rico-Lattes
    • 1
  1. 1.Laboratoire des IMRCP UMR 5623 CNRS, Université Paul SabatierToulouseFrance
  2. 2.Service Commun Rayons-X ICT-FR2599Université Paul SabatierToulouseFrance
  3. 3.Kiev National Taras Shevchenko UniversityKievUkraine

Personalised recommendations