ISSN 1070-3632, Russian Journal of General Chemistry, 2013, Vol. 83, No. 9, pp. 1792–1793. © Pleiades Publishing, Ltd., 2013.
Original Russian Text © S.D. Fazylov, O.A. Nurkenov, Sh.K. Amerkhanova, I.S. Tolepbek, 2013, published in Zhurnal Obshchei Khimii, 2013, Vol. 83,
No. 9, pp. 1577–1578.
LETTERS
TO THE EDITOR
The Interaction of Thiazolidine-2,4-dione
with an Aromatic Aldehyde Under Microwave Irradiation
S. D. Fazylova, O. A. Nurkenova, Sh. K. Amerkhanovab, and I. S. Tolepbeka
a Institute of Organic Synthesis and Coal Chemistry of the Republic of Kazakhstan,
ul. Alikhanova 1, Karaganda, 100008 Kazakhstan
e-mail: iosu8990@mail.ru
b Buketov Karaganda State University, Karaganda, Kazakhstan
Received May 30, 2013
DOI: 10.1134/S1070363213090284
Due to the development and use of the resource-
saving technologies, the effect of microwave field on
the known organic reactions has been comprehensively
investigated [1–3]. The advantages of microwave
irradiation over traditional activation sources are uni-
form heating of the reaction mixture, heating zero lag,
and significant reduction of the reaction time.
The so prepared thiazolidine-2,4-dione derivatives
were yellow (II) or white (III, IV) crystalline
substances, soluble in polar organic solvents. Structure
and purity of the obtained compounds were confirmed
by 1H NMR spectroscopy and elemental analysis.
General procedure for the synthesis of thia-
zolidine-2,4-dione derivatives II–IV under convec-
tion heating. 1.64 g (0.02 mol) of anhydrous sodium
acetate and 2.65 g (0.025 mol) of an aromatic aldehyde
in 10 ml of acetic acid was added to 2.34 g (0.02 mol)
of thiazolidine-2,4-dione I. The reaction mixture was
refluxed for 8–9 h. The course of the reaction was
monitored by TLC. The resulting precipitate was
filtered off and recrystallized from acetic acid.
We explored the possibility of thiazolidine-2,4-
dione 5-arylidene derivatives II–IV synthesis under
microwave irradiation according to the following
scheme.
H
N
H
N
O
O C
C O
CH3COOH
+
R
C
O C
C O
C
S
−H2O
HC
R
S
H
General procedure for the synthesis of thiazol-
idine-2,4-dione derivatives II–IV under microwave
activation. 1.64 g (0.02 mol) of anhydrous sodium
acetate and 2.65 g (0.025 mol) of an aromatic aldehyde
in 10 ml of acetic acid was added to 2.34 g (0.02 mol)
of thiazolidine-2,4-dione I. The reaction mixture was
irradiated for 5 min at 500 W with short interruptions
of irradiation every 10 s. The reaction progress was
monitored by TLC. After cooling, the formed pre-
cipitate was filtered off and recrystallized from acetic
acid.
II−IV
I
R = p-F-C6H4 (II), p-CH3O–C6H4 (III);
o,p-(CH3O)2–C6H3 (IV).
Thiazolidine-2,4-dione derivatives were prepared
under standard conditions with convection heating
(70–80°C, 8–9 h). Then the reaction mixture was
concentrated, and the desired product was isolated
[3, 4]. The main drawback of the method was the
reaction duration.
In the case of microwave activation, the reaction
conditions were investigated by changing the irradia-
tion duration (1 to 20 min) and irradiation power (70 to
750 W). The optimal conditions were: irradiation power
of 500 W and reaction duration of 2–5 min. Under
those conditions, yield of II–IV was of 65–72%.
5-(4-Fluorobenzylidene)thiazolidine-2,4-dione (II).
Yield 1.97 g (48%) (convection heating), 3.5 g (78%)
(microwave activation), yellow powder, mp 218–219°C.
1Н NMR spectrum (500 MHz), δ, ppm (J, Hz): 7.39 d
(2Н, Ar, J 8.9), 7.67 d (2H, Ar, J 8.6), 7.81 s (1H,
CH=), 12.55 s (1H, NH).
1792
Fazylov
