К 70-летию академика юнусова марата сабировича

MONONITRILE-FUNCTIONALIZED IONIC LIQUID
CATALYZED EFFICIENT ONE-POT SYNTHESIS
OF 2-PYRROLO-3’-YLOXINDOLES
 
O. Radul, T. Yudin, E. Stingaci, S. Pogrebnoi, F. Macaev
 
Institute of Chemistry, Academy of Sciences of Moldova, Academiei 3,
MD-2028, Chisinau, Moldova 
[e-mail] and [e-mail]
 
Ionic liquids participated organic reactions have been applied as an useful protocol in organic 
synthesis due to such approach often leads to shorter reaction times, increased yields, easier wor-
kup, matches with green chemistry protocols, and may enhance the region- and stereo-selectivity of 
reactions.
Oxindoles as well as pyrroles are one of the most prevalent heterocyclic compounds, which 
are present as the basic cores in many potent pharmaceutical compounds, natural products and var-
ious kinds of useful materials. In view of their importance, the development of simple method for 
the synthesis of substances with both moieties is of importance. As part of our current studies on 
design of new approach for the preparing of biologically active organic compounds and in the ap-
plication of functionalized ionic liquids we report herein a clear, facile and highly efficient method 
for addition ammonium acetate 3 and ethyl acetoacetate 2 to 3-phenacylideneoxindole 1 [1,2] in the 
presence of mononitrile-functionalized ionic liquids 4 [3]. 
H
N
O
EtO
O
Ph
O
+
1
HO
N
H
4
O
A
c
N
N
CN
CI
H
N
O
5
N
H
CO
2
Et
(10 mol%)
EtOH, reflux
Yield 82 %
2
3
4
Reaction was carried out by reflux of mixture compounds 1-3 and salt 4 (10 mol%) in ethanol 
for 1 hour. The structure of compound 5 was confirmed by elemental analysis, IR, 
1
H and 
13
C NMR 
spectroscopy.
In conclusion, we have developed an efficient method for the preparation of ethyl 2-methyl-4-
(2-oxo-2,3-dihydro-1H-3-indolyl)-5-phenyl-1H-3-pyrrolecarboxylate 5 as biologically interesting 
compound via mononitrile-functionalized ionic liquid 4 assisted coupling of ammonium acetate, 
ethyl acetoacetate and 3-phenacylideneoxindole.
1. Macaev F.Z., Radul O.M., Shterbet I.N., Pogrebnoi S.I., Sucman N.S., Malinovskii S.T., 
Barba A.N., Gdaniec M. Chemistry of Heterocyclic Compounds, 43, 298, 2007. 
2. Macaev F., Gavrilov K., Munteanu V., Stingaci E., Vlad L., Bet L., Pogrebnoi S., Barba A. 
Chem. Nat. Comp. 2, 114, 2007. 
3. Sargarovschi
 V., Stingaci E., Macaev F. Chem. J. Moldova, 2, 95, 2008.