Imidazole and its derivatives are well known biologically active and medicinally potent
anticancer [1], anti-HIV [2], antibacterial and antifungal [3], as well as cardiovascular active
compounds [4], etc. Moreover, imidazolium salts are potent room temperature ionic liquids [5,6].
The aim of this work was to synthesize new azaheterocyle salts derived from 1,3-diazoles via
conventional heating and ultrasound irradiation.
In order to obtain the desired 1,3-diazole salts, we performed the alkylation of some fivemember
rings N-heterocyles derived from imidazole and benzimidazole. Thus, imidazolium salts
were obtained in two steps: initially we carried out the N-alkylation of the acidic nitrogen of
imidazole derivatives via Michael addition of acrylonitrile; in the second step we carried out the
quaternization of the second nitrogen atom with iodoacetamide and methyl- or ethyl
bromoacetate, respectively.
Since not all obtained imidazolium salts are ionic liquids we have made anion metathesis in
order to change halogen anion with hexafluorophosphate or methyl sulphate anions.

In conclusion, we synthesized some new imidazole derivatives possible ionic liquids both by
conventional heating and ultrasound irradiation.
Under ultrasound irradiation the reaction time was dramatically reduced from 48 hours to 45
minutes.
The structure of the new compounds was proven by elemental (C, H, N) and spectral analysis
(IR, 1H NMR, 13C NMR, 2D-COSY, HMQC, HMBC). All the elemental and spectral data are in
accordance with the proposed structure.
Acknowledgements: To CNCS - UEFISCDI, grant PN-II-TE/ 0010 -79/05.10.2011 (director
assisting profesor Costel Moldoveanu) for financial support.
References:
1. G.K. Dy, A.A. Adjei, Cancer, 113, 1857 (2008).
2. S. Dubey, Y.D. Satyanarayana, H. Lavania, Eur. J. Med. Chem., 42, 1159 (2007).
3. R. Ells, J.L.F. Koch, P.W.J. Van Wyk, R.J. Milani, Antimicrob. Chemotherapy, 63, 124 (2009).
4. F. Adam, A. Kauscot, J.P. Rosa, M.J. Brickaert, Thrombosis and Haemostasis, 6, 2007, (2008).
5. P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, Ed. Wiley-VCH, Weinheim, (2008).
6. F. Macaev, V. Munteanu, E. Stingaci, A. Barba, S. Pogrebnoi, Chem. J. of Moldova, 2, 119,
(2007).