Russian Journal of Applied Chemistry, 2010, Vol. 83, No. 4, pp. 707−711.
Pleiades Publishing, Ltd., 2010.
Original Russian Text
E.N. Garibov, I.A. Rzaeva, N.G. Shykhaliev, A.I. Kuliev, V.M. Farzaliev, M.A. Allakhverdiev, 2010, published in Zhurnal Prikladnoi
Khimii, 2010, Vol. 83, No. 4, pp. 655−659.
AND INDUSTRIAL ORGANIC CHEMISTRY
Cyclic Thioureas as Cumene Oxidation Inhibitors
E. N. Garibov
, I. A. Rzaeva
, N. G. Shykhaliev
, A. I. Kuliev
, V. M. Farzaliev
and M. A. Allakhverdiev
Kuliev Institute of Chemistry of Additives, National Academy of Sciences of Azerbaijan, Baku, Azerbaijan
Baku State University, Baku, Azerbaijan
Received August 4, 2009
Hexahydro-1,3,5-triazine-4-thiones were synthesized by ternary condensation of thiourea with
various aldehydes and amines. The products were characterized by IR and NMR spectroscopy, and their
inhibiting effect on cumene oxidation was examined.
Thiourea and its derivatives are convenient starting
compounds for preparing various heterocyclic systems
Also, N-substituted thioureas exhibit a wide spectrum
of physiological activity. Some of these compounds
show antitumor, antiviral, antibacterial, and therapeutic
activity . The chemistry of heterocyclic compounds
synthesized from thiourea and its derivatives is one of
the most interesting and rapidly developing ﬁ elds of the
modern organic chemistry. Such heterocycles are used
as pharmaceuticals, chemical agents for plant protection,
bioprotectors for fuels and lubricating oils, antioxidants,
ﬁ reprooﬁ ng agents, and additives to polymeric materials
for imparting to them special properties [3–6]. Thietanyl
derivatives and other substituted thioureas show high
antioxidant activity [7, 8].
We synthesized cyclic thioureas by ternary
condensation of thiourea, various aldehydes, and
primary amines [7–10] and examined the correlation
between their structure and antioxidant properties (see
With aqueous ammonia used in the ternary
condensation, the reaction is usually performed at room
temperature for 20–40 h. With amines, the reaction is
performed at 60–70°C for 3 h in benzene. The formation
of cyclic thioureas I–VI is monitored by thin-layer
chromatography. Cyclic thioureas I–VI are white ﬁ nely
crystalline substances. They are readily soluble in
acetone, ethanol, and dimethyl sulfoxide.
The physicochemical constants, yields, and other
parameters are given in Table 1.
The structure of the synthesized cyclic thioureas I–
VI was proved by IR and
С NMR spectroscopy,
and the purity, by elemental analysis and thin-layer
In the IR spectra of I–VI, the absorption band at
corresponds to stretching vibrations of
the С=S bond. It should be noted that the С=S band, in
contrast to the С=О band, is not always readily revealed.
The С(S)N vibrations are observed at 1340–1245 cm
. Generally the С(S)N stretching vibrations are
R + H
R = H, R' = CH
(I); R = H, R' = CH
(II); R =
H, R' = (CH
C (III); R = H, R' = C
(IV); R =
H, R' = C
(V); R = C
–OH-2, R' = H (VI).