Skip to main content
Log in

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

  • Original Article
  • Published:
Journal of Surfactants and Detergents

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2
Fig. 6
Scheme 3
Fig. 7
Scheme 4
Scheme 5
Scheme 6

Similar content being viewed by others

References

  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 33:1222–1225

    CAS  Google Scholar 

  2. Lerner LJ (1989) Development of novel embryotoxic compounds for interceptive fertility control in the dog. J Reprod Fertil Suppl 39:251–265

    CAS  Google Scholar 

  3. Bonnett R, North SA (1981) The chemistry of the isoindoles. Adv Heterocycl Chem 29:341–399

    CAS  Google Scholar 

  4. Kreher R, Herd K-J (1982) Tricyclische 2H-isoindole Reaktionspartner fur CC- und NN-Dienophile. Chem–Ztg 106:305–308

  5. Kreher RP, Kohl N (1984) An economical preparation method for 2H-isoindoles. Angew Chem 96:507–508

    Article  CAS  Google Scholar 

  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 121:927–934

    Article  CAS  Google Scholar 

  7. Bonnett R, North SA, Newton RF, Scopes DI (1983) Substitution and addition reactions of isoindoles. Tetrahedron 39:1401–1405

    Article  CAS  Google Scholar 

  8. Kovtunenko VA, Voitenko ZV (1994) The chemistry of isoindoles. Russ Chem Rev 63:997–1018

    Article  Google Scholar 

  9. Kreher RP, Feldhoff U, Seubert J, Schmitt D (1987) Isoindoles and isoindolenines. Part 25. 2-Aryl-2H-isoindoles. Chem–Ztg 111:155–169

    Google Scholar 

  10. Orti E, Bredas JL (1988) Electronic structure of metal-free phthalocyanine: a valence effective Hamiltonian theoretical study. J Chem Phys 89:1009–1017

    Article  CAS  Google Scholar 

  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 123:381–390

    Article  CAS  Google Scholar 

  12. Zhou Z, Parr RG (1989) New measures of aromaticity: absolute hardness and relative hardness. J Am Chem Soc 111:7371–7379

    Article  CAS  Google Scholar 

  13. Troll T, Ollmann GW (1981) Preparation and reactions of l,3-bis-(trimethylsilyloxy)-isobenzofurans and –isoindoles. Tetrahedron Lett 22:3497–3500

    Article  CAS  Google Scholar 

  14. Pokholenko AA, Voitenko ZV, Kovtunenko VA (2004) Pyrido- and pyrimidoisoindoles: methods of synthesis and properties. Russ Chem Rev 73:771–784

    Article  CAS  Google Scholar 

  15. Veber DF, Lwowski W (1963) 1-arylisoindoles. J Am Chem Soc 85:646–647

    Article  CAS  Google Scholar 

  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 66:508–512

    Article  CAS  Google Scholar 

  17. Grieco PA (1998) Organic synthesis in water. Blackie Academic, New York

    Book  Google Scholar 

  18. Otto S, Engberts JBFN (2000) Diels–Alder reactions in water. Pure Appl Chem 72:1365–1372

    Article  CAS  Google Scholar 

  19. Otto S, Engberts JBFN (2001) In reactions and synthesis in Micellar media. Marcel Dekker, New York, pp 247–263

    Google Scholar 

  20. Theo R, Engberts JBFN (2002) Micellar catalysis of Diels–Alder reactions: substrate positioning in the micelle. J Org Chem 67:7369–7377

    Article  Google Scholar 

  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 12:45–53

    Article  CAS  Google Scholar 

  22. SAINT-NT (2000) Bruker AXS Inc.: Madison, Wisconsin

  23. SADABS, Program for data correction, Bruker − AXS

  24. Sheldrick GM (2008) A short history of SHELX. Acta Crystallog Sect A 64:112–122

    Article  CAS  Google Scholar 

  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 35:209–213

    Article  CAS  Google Scholar 

Download references

Acknowledgments

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).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Isabelle Rico-Lattes.

About this article

Cite this article

Levkov, I.V., Cassel, S., Voitenko, Z.V. et al. Synthesis, Autoorganization and Reactivity of Amphiphilic Derivatives of 1-Aminoisoindole in Water and Formamide. J Surfact Deterg 17, 101–109 (2014). https://doi.org/10.1007/s11743-013-1476-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11743-013-1476-y

Keywords

Navigation