Reactions of hydroxyphenyl-substituted 1,2,4-triazoles with electrophylic reagents

Article abstract of DOI:10.1134/S1070363209100259

Reactions of hydroxyphenyl substituted 1,2,4-triazoles with various electrophylic reagents were studied. Despite of the presence of several nucleophilic centers in the molecule, the reactions were shown to proceed regioselectively, with the formation of N

Full text of DOI:10.1134/S1070363209100259

ISSN 1070-3632, Russian Journal of General Chemistry, 2009, Vol. 79, No. 10, pp. 2234–2243. © Pleiades Publishing, Ltd., 2009.
Original Russian Text © E.Yu. Shasheva, N.I. Vikrishchuk, L.D. Popov, A.D. Vikrishchuk, I.E. Mikhailov, K.A. Lysenko, M.E. Kletskii, 2009, published in
Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 10, pp. 1739–1748.
Reactions of Hydroxyphenyl-Substituted 1,2,4-Triazoles
with Electrophylic Reagents
E. Yu. Shashevaa, N. I. Vikrishchuka, L. D. Popova,
A. D. Vikrishchukb, I. E. Mikhailovb, K. A. Lysenkoc, and M. E. Kletskiia
a Southern Federal University, Chemical Faculty,
ul. Zorge 7, Rostov-on-Don, 344090 Russia
e-mail: natvi2004@mail.ru
b Southern Scientific Center of Science of the Russian Academy of Sciences, Rostov-on-Don, Russia
c Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, Russia
Received January 23, 2009
Abstract—Reactions of hydroxyphenyl substituted 1,2,4-triazoles with various electrophylic reagents were
studied. Despite of the presence of several nucleophilic centers in the molecule, the reactions were shown to
proceed regioselectively, with the formation of N-substituted 3-(2-hydroxyphenyl)-1,2,4-triazoles. As a result
of the reactions of alkylation, tosylation, sulfoamination and aminomethylation by Mannich reaction earlier
unknown potential biologically active N-derivatives of 1,2,4-triazole were obtained.
DOI: 10.1134/S1070363209100259
Interest to 1,2,4-triazoles and to their derivatives is
caused by a wide spectrum of properties of these
compounds useful for practical applications. Among
1,2,4-triazoles there are herbicides [1], nematocides
[2], tranquilizers [3], substances with analget and
antihypoxit action [4]. Moreover, hydroxyphenyl-
substituted 1,2,4-triazoles easily formed from 4-oxo-
1,3-benzoxazinium perchlorates [5] under the action of
hydrazine-hydrate [6] contain in their structures
several reaction centers that expands their synthetic
opportunities and therefore they are interesting objects
for further chemical transformations. Because of the
ability of 1,2,4-triazoles and their derivatives to tauto-
meric transformations there are problems connected
with selectivity of the reaction course and identifica-
tion of the formed isomeric compounds. Therefore the
purpose of the present work was the preparation of
new 1,2,4-triazoles and the study of their reactions for
the expansion of the base of potential biologically
active substances.
At heating a suspension of 4-oxo-1,3-benz-
oxazinium perchlorates (Ia–Ij) [5, 7] with hydrazine
hydrate [6] in glacial acetic acid recyclization of salts I
occurs with the formation of before not described
arylvinyl- and hetarylvinyl derivatives of hydroxy-
phenyl substituted-1,2,4-triazoles (IIa–IIj) not known
before (Scheme 1).
Scheme 1.
O
OH
R
N2H4 H O
·
NH
2
N
ClO4_
R
+
O
N
N
H
Ia_Ij
IIa_IIj
R = 4-MeOC6H4 (a), 3,4-(MeO)2C6H3 (b), R = 4-MeSC6H4 (c), R = 4-ClC6H4 (d), R = 4-BrC6H4 (e), R = 2-thienyl (f), R =
1-methylindol-3-yl (g), R = 3-methylthienyl (h), R = 2-pyridinyl (i), R = 5-methylfuryl (j).
2234

REACTIONS OF HYDROXYPHENYL-SUBSTITUTED 1,2,4-TRIAZOLES
2235
Scheme 2.
R
N
R
R
3
H
4
N
H
H
O
N
O
N
N H
N2
5
N
H
1
N
N
H
O
C
B
A
CIR'
CIR'
CIR'
R
N
R
R
R'
H
H
O
N
O
N
N
N R'
N
N
H
N
N
R'
O
F
E
D
R = Me, ArCH
N
O, Ts, SO2NMe2.
CH; R' = Alk,
Formation of just 5-(2-hydroxyphenyl)-1Н-1,2,4-
triazoles (A) rather than compounds with isomeric
structures (B, C) (Scheme 2) in this reaction has been
proved earlier [8] and is confirmed by us on the basis
of the data of 13C NMR spectroscopy and gas phase
quantum-chemical DFT-calculations in В3LYP/6-31G
basis.
The data of gas-phase quantum-chemical DFT-
calculations in В3LYP/6-31G basis also specify the
preferable formation of the the triazole IIa as the
energetically most favorable isomer A, as follows from
the energy values for tautomeric forms
A
(–609655.52 kcal mol–1), B (–609644.72 kcal mol–1)
and C (–609655.02 kcal mol–1) (Scheme 2).
13
In the C NMR spectrum of 5-(2-hydroxyphenyl)-
The structure of the synthesized arylvinyl- and
heterylvinyl-substituted 1,2,4-triazoles IIa–IIi has
been established also by means of the elemental
3-methyl-substituted 1,2,4-triazole IIk the signal of
carbon C3 (Scheme 3) of triazole ring appears as a
quadruplet due to the long-range spin–spin coupling
with the protons of CН3 group (155.1 ppm, 2J = 7.3 Hz),
and the signal of carbon C5 of triazole ring looks like a
multiplet at 158.6 ppm as a result of long-range spin–
spin coupling with two proton groups (CН6 of phenol
substituent and NH), that indicates the existence of
compound IIk in the solution in DMSO as isomeric
form A.
1
analysis, IR, and Н NMR spectroscopy. In the IR
spectra of triazoles IIb, IId, IIe, and IIg to the
hydroxy group correspond the bands in the area of
3210–3190 cm–1, while in the case of compounds IIc,
IIf and IIh–IIj because of strong intramolecular
hydrogen bonding this band is not found in this area.
In the IR spectra of arylvinyl- and hetarylvinyl-
substituted 1,2,4-triazoles (unlike those of earlier
synthesized methyl- and phenylvinyl-substituted
triazoles [6]) there are strong absorption bands at
1660–1610 cm–1 of the double bond conjugated with
phenyl group, and a set of bands of moderate intensity
in the region of 1600–1580 cm–1, caused by the
sskeleton vibrations of aromatic and hetero-cyclic
rings. The presence of strong hydrogen bond between
phenol hydroxyl and nitrogen atom of the heterocycle
is indicated also by the essential downfield shift in the
1H NMR spectra of 1,2,4-triazoles II of the signal of
OH group proton (11.55–14.38 ppm) in comparison
with free phenols (4.00–7.50 ppm) [9]. In addition, in
Scheme 3.
151.1 q, 1J 7.3
Me
C3
OH
N
N
N
H
H6
158.6 m
C5
IIk
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

2236
SHASHEVA et al.
1
Scheme 4.
the H NMR spectra of azoles IIa–IIj doubling of the
peaks of triazole ring NH protons and phenol OH
protons occurs owing to restricted rotation around
C(phenol)–C(triazole) bond caused by intramolecular
hydrogen bonds.
R
H
HCl
X
O
N
N
Cl(CH2)2X
IIa_IIc, IIk, IIl
N
Because of the possible tautomeric transformations
of 1,2,4-triazoles II in solutions (Scheme 2) it was
necessary to elucidate in what tautomeric form and,
hence, with the formation of what isomer [N-derivative
of 5-(2-hydroxyphenyl)-4Н- (D), 5-(2-hydroxyphe-
nyl)-1Н- (E) or 3-(2-hydroxyphenyl)-1Н-1,2,4-tri-
azole) (F)] proceeds the reactions of 1,2,4-triazoles
with various electrophylic reagents.
IIIa_IIIh
IIIa_IIIc, X = NEt2
IIId, IIIe, X =
IIIe_IIIh, X =
N
N
O
II: R = 4-MeOC6H4CH=CH (a), R = 3,4-(MeO)2C6H3·
CH=CH (b); R = 4-MeSC6H4CH=CH (c), R = Me (k), R =
Ph–CH=CH (l); III: R = PhCH=CH (a), R = 4-MeO·
C6H4CH=CH (b), R = 4-MeSC6H4CH=CH (c), R = Me (d),
R = 3,4-(MeO)2C6H3 (e), R = PhCH=CH (f), R = 4-MeO·
C6H4CH=CH (g), R = 3,4-(MeO)2C6H3CH=CH (h).
The distignishing of the structure of the formed
isomer is of principal significance because the
character of substitution should influence essentially
the biological activity of the formed compounds.
As a result of reaction of triazoles IIa–IIc, IIk and
IIl with dialkylaminoethyl chlorides [(2-chloroethyl)
diethylamine, 4-(2-chloroethyl)morpholine and 1-(2-
chloroethyl)piperidine] at boiling in acetone in the
presence of NaOH were synthesized triazoles IIIa–IIIi
(Scheme 4). To increase the solubility of compounds
IIIa–IIIi in water and in water–organic media they
were isolated from the reaction mixtures in the form of
hydrochlorides.
philic centers, in this reaction (Scheme 4) were
isolated in 43–56% yield only N-derivatives of 3-(2-
hydroxy-phenyl)-1Н-1,2,4-triazole
IIIa–IIIh,
as
follows from the data of Н (COSY) and 13C NMR
spectroscopy. From the analysis of a two-dimentional
1Н (COSY) NMR spectrum (Fig. 1) of compound IIIa
in the region of 6.91–11.05 ppm, it is possible to
conclude that the proton of phenol hydroxyl is coupled
1
Despite the presence in the molecules hyd-
roxyphenyl-substituted triazoles of several nucleo-
2
4
6
8
10
12
10
8
6
4
2
δ, ppm
1
Fig. 1. Two-dimensional H NMR (COSY) spectrum of 2-{1-[2-(diethylamino)ethyl]-5-[2-phenylvinyl]-1Н-1,2,4-triazol-3-yl}
phenol hydrochloride (IIIa).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

REACTIONS OF HYDROXYPHENYL-SUBSTITUTED 1,2,4-TRIAZOLES
2237
with the proton at the carbon C3, as follows from the
existence of the corresponding correlation peaks.
triazoles Va and Vb (Scheme 6). In the IR spectra of
compounds Va, Vb, owing to strong intramolecular
hydrogen bond the absorption of hydroxy groups at
3300–3100 cm–1 did not appear, but there were ab-
sorption bands at 1630–1560 cm–1 caused by skeleton
For revealing direction of 1,2,4-triazoles alkylation
with alkylaminoethyl chlorides, the spectrum of 13C
NMR monoresonance of compound IIIb was
registered. In the spectrum the signal of carbon C3 of
triazole ring appears as a doublet due to the long-range
spin–spin coupling with the proton H6 of phenolic
substituent (159.32 ppm, 3J = 4.4 Hz), and the signal of
carbon C5 of triazole ring is a multiplet due to the
spin–spin coupling with two groups of protons (CН
1
vibrations of aromatic and heterocyclic rings. The H
NMR spectra of azoles Va and Vb contain the four-
proton triplets in the range of 2.68–3.65 ppm,
characteristic of the morpholine fragment. There is a
signal at 5.31–5.36 ppm of the NCН2 group protons as
a singlet due to free rotation around C–N bond, unlike
the phenothiazine derivative IV. In the range of 6.99–
8.09 ppm the multiplets were observed of aromatic
protons. Similarly to the spectra of triazoles IIa–IIj the
signal of phenol hydroxyl of compounds IVa, IVb and
Va, Vb is shifted from the region of 4.0–7.5 ppm
characteristic of free phenols [9] downfield to 11.05–
13.20 ppm owing to strong intramolecular hydrogen
bonding.
3
vinyl and CН2, 152.86 ppm, 2J = 4.8 Hz, J = 1.2 Hz),
that proves the reaction course with the formation of
3-(2-hydroxyphenyl)-1Н-1,2,4-triazole N-derivative. It
is known that phenothiazine derivatives show high
antioxidant,
antiradical,
neuroprotecting
and
antineoplastic activity [10–14]. With the purpose of
synthesis of the compounds containing pheno-thiazine
fragment we developed a way of introduction of this
fragment into 2-hydroxyphenyl-1,2,4-triazoles. By
boiling 1,2,4-triazoles IIb and IIf with 2-chloro-10-
(chloroacetyl)-10Н-phenothiazine in acetone in the
presence of potassium carbonate we prepared in high
yield new heterocyclic compounds IVa and IVb
(Scheme 5) whose structure was proved by the data of
elemental analysis, IR, and 1H NMR spectroscopy.
The direction of triazoles IIb and IIl amino-
metilation has been revealed by an example of com-
pound Va. In its 13C NMR monoresonance spectrum
the signal of C3 carbon nucleus of triazole ring is a
doublet as a result of long-range spin–spin coupling
with the proton Н6 of the phenol substituent (δC
3
160.2 ppm, J = 4.5 Hz), and the signal of carbon C5
In the 1H NMR spectra of the phenothiazine
derivatives IVa and IVb in the range of 6.90–8.01 ppm
the multiplets of aromatic protons were observed, and
because of absence of symmetry elements in these
compounds the signals of protons of prochiral CН2
group at 20°C appear at 5.36–5.75 ppm in the form of
two broad doublets, that, possibly, is caused by the
restricted amide rotation around C–N bond.
nucleus is a multiplet as a result of long-range spin–
spin coupling with two proton groups (CН vinyl and
2
3
CН2, δC 154.25 ppm, J = 5 Hz, J = 2.6 Hz), that
proves the formation in the Mannich reaction of 1-
morpholinomethyl-5R-substituted derivatives Va, Vb.
We developed the methods of synthesis of N-tosyl-
and N-sulfamoyl-substituted 1,2,4-triazoles VIa–VId
and VIIa–VIId. The target products are formed at
heating of 1,2,4-triazoles IIa–IIc, IIe, and IIk in
pyridine with tosyl or sulfamoyl chloride (Scheme 6).
The Mannich aminometylation of 1,2,4-triazoles
IIb and IIl affords morpholinomethyl-substituted 1,2,4-
Scheme 5.
Cl
Cl
O
R
N
S
OH
N
N
Cl
N
N
IIb, IIf
S
O
IVa, IVb
II: R = 3,4-(MeO)2C6H3=CH– (b), R = 2-thienylvinyl (f); IV: R = 3,4-(MeO)2C6H3CH=CH– (a), R = 2-thienylvinyl (b).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

2238
SHASHEVA et al.
Scheme 6.
IIa_IIc, IIe, IIk, IIl
ClSO2NMe2
CH2O
Py
TsCl
R
N
morpholin
R
OH
N
R
H
H
O
O
N
N
N
SO2
N
N
N
N
SO2
N(CH3)2
N
O
VIIa_VIId
Va, Vb
VIa_VId
CH3
II: R = 4-MeOC6H4CH=CH (a), 3,4-(MeO)2C6H3CH=CH (b), R = 4-MeSC6H4CH=CH (c), R = 4-BrC6H4CH=CH (e), R =
СH3 (k), R = PhCH=CH (l); V: R = 4-MeOC6H4CH=CH (a), R = 3,4-(MeO)2C6H3CH=CH (b); VI: R = Me (a), R =
PhCH=CH (b), R = 3,4-(MeO)2C6H3CH=CH (c), R = 4-BrC6H4CH=CH (d); VII: R = Me (a), R = PhCH=CH (b), R = 3,4-
(MeO)2C6H3CH=CH (c), R = 4-MeSC6H4CH=CH (d).
The tosyl and sulfamoyl groups do not allow to
elucidate the position of replacement in 1,2,4-triazole
ring at the identification of isomers by means of 13C
NMR spectroscopy. Therefore we applied X-ray
structural is shown analysis. In Fig. 2 the molecular
structure of compound VIId according to X-ray
structural analysis that, like the products of alkylation
and aminometylation, corresponds to N-substituted 3-
(2-hydroxyphenyl)-1Н-1,2,4-triazole.
The compositions and structures of the obtained
compounds VI and VII are confirmed by the data of
1
elemental analysis, IR, H NMR spectroscopy, and
also by the data of X-ray structural analysis of
compound VIId.
In a crystal the molecule actually is flat, except for
SO2NMe2 group. The torsion angle describing position
of the phenol substituent relatively to triazole ring
equals 5.1°, and the dihedral angle between the planes
of p-methylthiophenylvinylidene fragment and triazole
ring is 10.2°. Hydroxy group in the crystal participates
in the formation of strong enough intramolecular
O–H···N hydrogen bond with H1O···N1 distance
1.90 Å. The analysis of the crystal packing showed
that all intermolecular contacts correspond to usual van
der Waals interactions. The basic bond lengths and
bond angles are listed in Table 3.
C21
N5
S1
C22
N3
C10
C9
O2
O3
C11
C6
C2
N4
C5
C8
C7
N1
C12
1
O1
The 2D H NMR (COSY) spectrum of compound
C13
VIIa is well consistent with the data of X-ray struc-
tural analysis. It is seen from Fig. 3 that the proton of
the phenol hydroxyl interacts with the proton [CН3] of
the aromatic ring, that follows from the appearance of
the respective correlation peaks, hence, occurs the forma-
tion of N- rather than O-substituted 1,2,4-triazoles.
C15
C14
C19
C16
C17
C18
C20
S2
From the investigation carried out it is possible to
conclude that the reactions of hydroxyphenyl-
substituted 1,2,4-triazoles II with electrophylic reagents
proceed regioselectively with the formation of 3-(2-
hydroxyphenyl)-1Н-1,2,4-triazole N-derivatives.
Fig. 2. Molecular structure of 3-(2-hydroxyphenyl)-N,N-
dimethyl-5-{2-[4-(methylthio)phenyl]vinyl}-1Н-1,2,4-triazol-
1-sulfonamide (VIId) by the data of X-ray structural
analysis.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

REACTIONS OF HYDROXYPHENYL-SUBSTITUTED 1,2,4-TRIAZOLES
2239
Table 1. Principal bond lengths (Å) and bond angles (deg)
in the molecule of 3-(2-hydroxyphenyl)-N,N-dimethyl-5-{2-
[4-(methylthio)phenyl]vinyl}-1Н-1,2,4-triazol-1-sulfonamide
(VIId)
We established that sulfamoyl substituted 1,2,4-
triazoles VIIa and VIId display antibacterial activity
toward Staphylococcus aureus 209-P.
EXPERIMENTAL
Bond
Bond
Bond
d, Å
ω, deg
ω, deg
angles
angles
The elemental analysis of the synthesized com-
pounds was carried out on an automatic CHN analyzer
Perkin Elmer 240. The IR spectra were registered on a
Specord 75IR from suspensions in mineral oil, The 13C
O1–C7 1.354(3) O2S1O3 124.5(13) C2N3N4 102.2(2)
C2–N3 1.327(3) O2S1N5 116.8(10) C5N4N3 110.5(2)
C2–C6 1.465(4) O3S1N5 106.4(5)
N3–N4 1.376(3) O2S1N4 103(2)
C9–C10 1.383(4) O3S1N4
C10–C11 1.367(4) N5S1N4 104.51(12) N1C5C12 126.8(2)
C5N4S1 130.5819
N3N4S1 117.70(17)
N1C5N4 108.4(2)
1
1
and H NMR and 2D H NMR (COSY) spectra were
obtained on a Varian Unity spectrometer (300 MHz) at
20°C.
97.7(3)
Triazoles IIk and IIIl have been described in [6].
Yields, melting points (solvent for crystallization) and
the data of the elemental analysis of the synthesized
compounds II–VII are listed in Table 2, the data of IR
and a 1H NMR spectroscopy of compounds II–VII are
collected in Table 3.
C12–C13 1.321(4) C5N1C2 104.3(2)
N3C2N1 114.5(2)
N4C5C12 124.8(2)
C22N5C21 115.2(2)
C22N5S1 118.0(2)
C21N5S1 120.6(2)
N3C2C6 123.2(2)
N1C2C6 122.2(2)
2-(3-Methyl-1Н-1,2,4-triazol-5-yl)phenol (IIk). 13C
NMR spectrum (DMSO-d6), δ, ppm, J, Hz: 12.92 q
(1C, Мe, J = 129.2), 114.51 m (1C, Car), 117.6 m (1C,
Car), 120.05 m (1C, Car), 127.08 d (1C, Car, J = 5.6),
131.58 m (1C, Car), 155.09 q (1C, Ctriazole, J = 7.3),
157.10 m (1C, Car), 158.55 m (1C, Ctriazole, 2J = 5.2).
were filtered and washed with water. Crystals of light
brown color, yield 2.4 g.
Compound IIb–IIj were prepared similarly [6].
2-{3-[2-(3,4-Dimethoxyphenyl)vinyl]-1Н-1,2,4-tri-
azol-5-yl}phenol (IIb), brown crystals.
2-(3{(2-[4-(Methylthio)phenyl]vinyl}-1Н-1,2,4-tri-
azol-5-yl)phenol (IIc), yellow crystals.
2-{3-[2-(4-Methoxyphenyl]-1Н-1,2,4-triazol-5-yl}-
phenol (IIa). A suspension of 10 mmol of perchlorate
Ia in 10 ml of glacial AcOH and 20 mmol of hydrazine-
hydrate was boiled for several minutes. The reaction
mixture was cooled to room temperature and after 6–
8 h keeping was diluted with water, the formed crystals
2-{3-[2-(4-Chlorophenyl)vinyl]-1Н-1,2,4-triazol-5-
yl}phenol (IId), colorless crystals.
2-{3-[2-(4-Bromophenyl)vinyl]-1Н-1,2,4-triazol-5-
yl}phenol (IIe) colorless crystals.
2
4
6
8
10
10
8
6
4
2
δ, ppm
Fig. 3. Two-dimensional 1H NMR (COSY) spectrum of 3-(2-hydroxyphenyl)-N,N,5-trimethyl-1Н-1,2,4-triazol-1-sulfonamide (VIIa).
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

2240
SHASHEVA et al.
Table 2. Yields, melting points and data of elemental analyses of compounds II–VII
Found, %
N
Calculated, %
Comp. Yield,
mp, °С
Formula
no.
%
C
H
Наl/S
C
H
N
Hal/S
81
56
61
49
57
34
45
50
38
36
55
51
49
48
42
52
43
55
97
75
55
53
54
47
43
43
59
46
52
52
186–188 (BuOH)
200–202 (BuOH)
198–200 (BuOH)
198–200 (BuOH)
210–212 (BuOH)
202–204 (i-PrOH)
235–236 (BuOH)
204–206 (BuOH)
228–230 (BuOH)
186–188 (BuOH)
146–147 (MeOH)
175–177 (BuOH)
70–72 (MeCN)
69.20
66.00
64.70
64.70
56.30
62.60
72.00
63.30
68.30
67.70
66.10
64.10
62.30
55.60
60.20
66.40
65.70
63.70
64.50
65.90
67.00
65.10
58.50
66.40
62.70
55.80
46.10
58.30
55.90
54.90
5.00 14.10
5.00 13.10
5.20 13.90
4.20 14.00
3.10 12.50
4.70 15.10
5.30 17.50
4.70 14.50
4.70 21.40
4.50 15.80
3.90 14.30
6.90 13.40
6.80 12.40
6.20 17.00
6.00 12.10
6.90 14.20
6.30 12.50
6.70 11.70
–
–
С17Н15N3O2
С18Н17N3O3
С17Н15N3OS
С16Н12ClN3O
С16Н12BrN3O
С14Н11N3OS
С19Н16N4O
69.62
66.87
64.65
64.54
56.14
62.45
72.15
63.60
68.18
67.42
66.25
64.41
5.00 14.10
5.26 13.00
5.05 14.14
4.03 14.12
3.51 12.28
4.09 15.61
5.06 17.72
4.59 14.84
4.55 21.21
4.87 15.73
6.78 14.05
6.77 13.07
–
–
IIa
IIb
10.70
11.70
23.00
11.10
–
10.70
11.93
23.39
11.90
–
IIv
IId
IIe
IIf
IIg
11.10
–
С15Н13N3OS
С15Н12N4O
11.31
–
IIh
IIi
–
С15Н13N3O2
С22Н27ClN4O
С23Н29ClN4O2
–
IIj
8.70
8.60
8.91
8.28
IIIa
IIIb
IIIc
IIId
IIIe
IIIf
IIIg
IIIh
IVa
IVb
Va
7.70/7.50 С23Н29ClN4OS 62.09
6.52 12.60 7.99/7.20
140–142 (i-PrOH)
163–165 (MeOH)
198–200 (i-PrOH)
192–193 (MeOH)
197–199 (BuOH)
187–189 (BuOH)
146–147 (BuOH)
160–162 (MeOH)
146–148 (i-PrOH)
177–179 (BuOH)
122–124 (BuOH)
152–154 (BuOH)
160–162 (BuOH)
123–125 (BuOH)
175–176 (BuOH)
169–171 (BuOH)
150–152 (BuOH)
11.10
7.10
9.00
7.90
7.40
С15Н21ClN4O2
С24Н29ClN4O4
С22Н27ClN4O
С24Н29ClN4O2
С25Н31ClN4O3
55.47
60.95
66.25
65.38
63.76
6.47 17.00
6.14 11.85
6.78 14.05
6.58 12.71
6.59 11.90
10.94
7.51
8.91
8.06
7.55
4.30
9.50
5.80/5.30 С32Н25ClN4O4S 64.38
6.90/6.20 С28Н19ClN4O2S 65.82
4.19
9.39 5.95/5.36
3.60 10.90
6.40 14.50
6.50 12.90
4.20 12.90
3.72 10.97 6.95/6.27
–
С22Н24N4O3
С23Н26N4O4
С16Н15N3O3S
С23Н19N3O3S
С25Н23N3O5S
67.35
65.40
58.36
66.19
62.89
6.12 14.29
6.16 13.27
4.56 12.77
4.56 10.07
–
–
–
Vb
10.00
7.80
6.60
9.73
7.67
6.72
VIa
VIb
VIc
VId
VIIa
VIIb
VIIc
VIId
4.70
4.90
3.50
9.80
8.90
8.60
4.82
3.63
8.81
16.2/6.30 С23Н18BrN3O5S 55.65
8.47 16.1/6.45
4.90 19.90
4.80 15.20
5.20 13.10
4.50 13.60
11.30
8.60
С11Н14N4O3S
С18Н18N4O3S
С20Н22N4O5S
С19Н20N4O3S2
46.10
58.38
55.81
54.81
4.96 19.86
4.86 15.14
5.12 13.02
4.81 13.46
11.35
8.65
7.50
7.44
15.10
15.38
Table 3. Data of IR and 1H NMR spectroscopy of compounds II–VII
Comp.
IR spectrum, ν, cm–1
1Н NMR spectrum, solvent, δ, ppm, J, Hz
no.
1640, 1630, 1610, 1560 (С=Сvinyl, C=Cар, DMSO-d6, 3.83 s (3H, ОМе), 7.27 and 7.67 d.d (2Н, СНvinyl, J 7.9), 6.92–7.95 m
С=N) (8Н, Наr), 11.98, 11.65 s (1Н, NН), 14.21 s (1Н, ОН)
3200 (OH); 1640 (C=C); 1610, 1590 (C=C, Acetone-d6, 3.81 s (3H, ОМе), 3.83 s (3H, ОМе), 6.92–7.91 m (9Н, Наr, СН-vinyl),
IIa
IIb
IIc
IId
IIe
IIf
С=N)
11.21, 11.62 s (1Н, NН), 14.28 s (1Н, ОН)
1630, 1610 (C=C); 1570 (C=C, С=N)
Acetone-d6, 2.55 s (3H, SMe), 7.01–8.09 m (10Н, Наr, СН-vinyl), 11.45, 11.73 s
(1Н, NН); 13.72 s (1Н, ОН)
3190 (OH); 1650, 1630 (C=C); 1560 (C=C, DMSO-d6, 6.92–7.99 m (10Н, Наr, СН-vinyl), 11.18, 11.61 s (1Н, NH), 14.38,
С=N) 14.42 s (1Н, ОН)
3210 (OH); 1650 (С=С); 1600, 1550 (C=C, DMSO-d6, 6.99–8.19 m (10Н, Наr, СН-vinyl), 11.21, 11.58 s (1Н, NH), 14.28 s
С=N)
(1Н, ОН)
1620, 1610 (С=С); 1560 (C=C, С=N)
DMSO-d6, 6.82–7.95 m (9Н, Наr, СН-vinyl), 11.08, 11.43 s (1Н, NН), 13.95, 14.24
s (1Н, ОН)
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REACTIONS OF HYDROXYPHENYL-SUBSTITUTED 1,2,4-TRIAZOLES
2241
Table 3. (Contd.)
Comp.
no.
IR spectrum, ν, cm–1
1Н NMR spectrum, solvent, δ, ppm, J, Hz
3200 (OH); 1640, 1610 (С=С); DMSO-d6, 3.90 s (3H, Me), 6.86–7.92 m (11Н, Наr, СН-vinyl), 11.33, 11.80 s (1Н, NH);
IIg
IIh
IIi
1590 (C=C, С=N) 13.88, 14.19 s (1Н, ОН)
1630, 1610 (С=С); 1560 (C=C, DMSO-d6, 2.27 s (3H, Me), 6.62–7.98 m (8Н, Наr, СН-vinyl), 11.01, 11.43 s (1Н, NH), 13.85,
С=N) 14.22 s (1Н, ОН)
1660 (С=N); 1600, 1580 (С=С); DMSO-d6, 6.91–8.58 m (10Н, Наr, СН-vinyl), 11.09, 11.55 s (1Н, NH)
1520 (C=C, С=N)
1630, 1610 (С=С); 1560 (C=C, DMSO-d6, 2.38 s (3H, Me), 6.09–7.92 m (8Н, Наr, СН-vinyl), 11.19, 11.49 s (1Н, NH),
IIj
С=N)
14.21 s (1Н, ОН)
1630 (C=N); 1590, 1540 (C=С)
DMSO-d6, 1.36 t (6Н, Ме, J 7.2), 3.23 m (4Н, СН2), 3.61 t (2Н, СН2, J 6.8), 5.08 t (2Н, СН2,
J 7.2), 6.91–7.99 m (11Н, Наr, СН-vinyl), 10.90 s (1Н, N+H), 12.28 s (1Н, ОН)
IIIa
IIIb
1650, 1650, 1570, 1520 (С=Сvinyl, Acetone-d6, 1.42 t (6Н, Ме, J 7.48), 2.47 s (3H, ОMe), 3.28 m (4Н, СН2), 3.70 t (2Н, СН2,
C=Сар, C=N)
J 6.9), 5.19 t (2Н, СН2, J 7.4), 6.91–8.07 m (10Н, Наr, СНvinyl), 11.15 s (1Н, N+H), 13.23 s
(1Н, ОН)
1640, 1630 (C=N); 1590, 1560 DMSO-d6, 1.41 t (6Н, Ме, J 7.50), 2.37 s (3H, SMe), 3.31 m (4Н, СН2), 3.71 t (2Н, СН2,
(C=С) J 6.9); 5.09 t (2Н, СН2, J 7.2), 6.99, 8.01 m (10Н, Наr, СН-vinyl)
IIIc
IIId
IIIe
1640, 1630 (C=N); 1560, 1530 DMSO-d6, 2.67 s (3H, Me), 3.12 t (2Н, СН2, J 7.5), 3.55 t (4Н, СН2, J 7.7), 3.95 t (4Н, СН2,
(С=С)
J 5.5), 4.8 t (2Н, СН2, J 5.8), 6.83–7.89 m (4Н, Наr), 10.87 s (1Н, N+H), 12.70 s (1Н, ОН)
DMSO-d6, 3.18 t (2Н, СН2, J 6.9), 3.45 t (2Н, СН2, J 5.7), 3.68 t (2Н, СН2, J 5.9),
3.81 s (3Н, OMe) 3.83 s (3H, ОМе), 3.95 t (4Н, СН2), 5.07 t (2Н, СН2), 6.89–7.95 m (9Н,
Наr, СН-vinyl), 10.92 s (1Н, N+H), 12.71 s (1Н, ОН)
1630, 1610 (C=N); 1530 (C=C)
1640, 1620 (C=N); 1580, 1550 DMSO-d6, 1.48–2.01 m (6Н, СН2), 2.99 t (2Н, СН2, J 7.7), 3.59 t (4Н, СН2, J 7.0), 5.09 t (2Н,
(C=C)
СН2, J 7.2), 6.89–7.93 m (11Н, Наr, СН-vinyl), 10.88 s (1Н, N+H), 11.99 s (1Н, ОН)
IIIf
1630, 1620 (C=N); 1580, 1560 DMSO-d6, 1.48–2.02 m (6Н, СН2), 2.98 t (2Н, СН2, J 7.5), 3.52 m (4Н, СН2), 3.83 s (3Н,
(C=C)
IIIg
ОМе); 5.05 t (2Н, СН2, J 7.0), 6.78–7.95 m (10Н, Наr, СН-vinyl), 10.95 s (1Н, N+H), 11.91 s
(1Н, ОН)
1630, 1610 (C=N); 1570, 1520 DMSO-d6, 1.48–1.99 m (6Н, СН2), 2.96 t (2Н, СН2, J 7.7), 3.51 m (4Н, СН2), 3.81 s (3Н,
IIIh
(C=C)
ОМе), 3.95 s (3Н, ОМе), 5.09 t (2Н, СН2, J 7.0), 6.95–7.95 m (9Н, Наr, СН-vinyl), 10.98 s
(1Н, N+H), 12.00 s (1Н, ОН)
1710 (С=О); 1630, 1600 (C=N); DMSO-d6, 3.60 s (3Н, ОМе), 3.70 s (3Н, ОМе), 5.75 d.br (2Н, СН2, J 5.6), 7.00–8.01 m
1550 (С=С) (16Н, Наr, СН-vinyl), 11.05 s (1Н, ОН)
1710 (С=О); 1630, 1605 (C=N); DMSO-d6, 5.60 d (2Н, СН2, J 5.6), 6.90–7.98 m (16Н, Наr, СН-vinyl), 11.10 s (1Н, ОН)
1510 (С=С)
IVa
IVb
Va
1630, 1620 (С=N); 1590, 1570 DMSO-d6, 2.73 t (4Н, СН2, J 6.9), 3.65 t (4Н, СН2, J 7.3), 3.89 s (3Н, ОМе), 5.31 s (2Н,
(С=С)
СН2) 6.99–8.09 m (10Н, Наr, СН-vinyl), 13.20 s (1Н, ОН)
1600 (С=N); 1580, 1560 (С=С)
DMSO-d6, 2.68 t (4Н, СН2, J 7.2), 3.60 t (4Н, СН2, J 7.2), 3.80 s (3Н, ОМе), 3.88 s (3Н,
ОМе), 5.36 s (2Н, СН2), 6.99–8.09 m (9Н, Наr, СН-vinyl), 11.15 s (1Н, ОН)
Vb
3190 (ОН); 1615 (C=N); 1540 DMSO-d6, 2.21 s (3Н, Ме), 2.30 s (3Н, Ме), 7.21–7.70 m (8Н, Наr), 13.61 s (1Н, ОН)
(С=С)
3200 (ОН); 1630 (C=N); 1530 DMSO-d6, 2.28 s (3Н, Ме), 6.99–7.88 m (15Н, Наr, СН-vinyl), 13.90 s (1Н, ОН)
(С=С)
VIa
VIb
VIc
VId
VIIa
VIIb
VIIc
VIId
3180 (ОН); 1630, 1615 (C=N); DMSO-d6, 2.32 s (3Н, Ме), 3.80 s (3Н, ОМе), 3.84 s (3Н, ОМе), 6.85–7.82 m (13Н, Наr, СН-
1550 (С=С)
vinyl), 13.80 s (1Н, ОН)
3190 (ОН); 1640 (C=N); 1540 DMSO-d6, 2.28 s (3Н, Ме), 7.06–7.89 m (14Н, Наr, СН-vinyl), 13.92 s (1Н, ОН)
(С=С)
1630 (C=N); 1590, 1580 (C=C)
1620, 1600 (C=N); 1590 (C=C)
1620, (C=N); 1590, 1560 (C=C)
1630, 1600 (C=N); 1590 (C=C)
DMSO-d6, 2.76 s (3Н, Ме), 3.08 s (6Н, NMe2), 6.88–7.91 m (4Н, Наr), 10.32 s (1Н, ОН)
DMSO-d6, 3.12 s (6Н, NМе2), 6.92–7.98 m (11Н, Наr, СН-vinyl), 10.38 s (1Н, ОН)
DMSO-d6, 3.11 s (6Н, NМе2), 3.82 s (3Н, ОМе), 3.85 s (3Н, ОМе), 6.87–8.01 m (9Н, Наr,
СН-vinyl), 10.44 s (1Н, ОН)
DMSO-d6, 2.47 s (3H, SMe), 3.08 s (6Н, NMe2), 6.91–7.92 m (10Н, Наr, СН-vinyl), 10.38 s
(1Н, ОН)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

2242
SHASHEVA et al.
13
Table 4. Crystallographic data and parameters of X-ray
structural experiment for compound VIIa
chloride (IIIb), colorless crystals. C NMR spectrum
(DMSO-d6), δ, ppm, J, Hz: 8.30 q (2C, CH3, J =
128.2), 42.43 t (1C, CН2, J = 114.2), 46.39 t (2C, CН2,
J = 143.0), 49.40 t (1C, CН2, J = 143.5), 55.21 q (1C,
OCН3, J = 144.7), 108.37 d (1C, Cvinyl, J = 5.8), 113.79
d (1C, Car, J = 6.6), 114.18 d (2C, Car, J = 8.4), 116.88
m (1C, Car), 119.3 m (1C, Car), 126.44 d (1C, Car, J =
9.4,), 127.86 t (1C, Car, J = 5.8),129.60 d (2C, Car, J =
8.1), 130.98 m (1C, Car), 137.78 m (1C, Cvinyl), 152.86
Parameter
Value
Formula
Molecular mass
Crystal system
Space group
a, Å
C19H20N4O3S2
416
Monoclinic
P21/с
6.4415(10)
17.069(3)
17.592(3)
92.423(14)
1932.5(6)
872
b, Å
2
3
m (1C, Cttriazole, J = 4.8 Hz, J = 1.2), 156.26 m (1C,
Car), 159.29 d (1C, Ctriazole, J = 4.4,), 160.41 m (1C, Car).
c, Å
β, deg
V, Å3
2-(1-[2-(Diethylamino)ethyl]-5-{2-[4-(methyl-
thio)phenyl]-vinyl}-1Н-1,2,4-triazole-3-yl)phenol
hydrochloride (IIIc), colorless crystals.
F(000)
Z
4
dcalc, g cm–3
μ, cm–1
1.432
2-[5-Methyl-1-(2-morpholin-4-ylethyl)-1Н-1,2,4-
triazol-3-yl]phenol hydrochloride (IIId), colorless
crystals.
3.04
Measured reflexes/total reflexes
Rint
10662/4578
0.0388
2408
2-[5-[2-(3,4-Dimethoxyphenyl)vinyl]-1-(2-morpho-
lin-4-ylethyl)-1Н-1,2,4-triazol-3-yl]phenol hydrochloride
(IIIe), colorless crystals.
Reflexes with I ≥2σ(I)
Number of refined parameters
R1 (I ≥ 2σ(I))
296
0.0576
0.1381
2-[5-[2-Phenylvinyl]-1-(2-piperidin-1-ylethyl)-1Н-
1,2,4-triazol-3-yl]phenol hydrochloride (IIIf), color-
less crystals.
wR2 (over all reflexes)
2-{3-[2-(2-Thienyl)vinyl]-1Н-1,2,4-triazol-5-yl}-
phenol (IIf) brown crystals.
2-[5-[2-(4-Methoxyphenyl)vinyl]-1-(2-piperidin-1-
ylethyl)-1Н-1,2,4-triazol-3-yl]phenol hydrochloride
(IIIg), colorless crystals.
2-{3-[2-(1-Methyl-1Н-indo-3-yl)vinyl]-1Н-1,2,4-tri-
azol-5-yl}phenol (IIg) colorless crystals.
2-[5-[2-(3,4-Dimethoxyphenyl)vinyl]-1-(2-pipe-
ridin-1-ylethyl)-1Н-1,2,4-triazol-3-yl]phenol hydro-
chloride (IIIh), colorless crystals.
2-{3-[2-(3-methyl-2-thienyl)vinyl]-1Н-1,2,4-triazol-
5-yl}phenol (IIh) yellow-brown crystals.
2-{3-[2-Pyrid-2-ylvinyl]-1Н-1,2,4-triazol-5-yl}-
phenol (IIi) brown crystals.
2-{1-[2-(2-Chloro-10Н-phenothiazin-10-yl)-2-oxo-
ethyl]-5-[2-(3,4-dimethoxyphenyl)vinyl]-1Н-1,2,4-tri-
azol-3-yl}phenol (IVa). To a solution of 10 mmol of
compound IIb in 15 ml of acetone was added 40 mmol
of calcined potassium carbonate, and the mixture was
boiled for 15 mines, then cooled, and 10 mmol of 3-
2-{3-[2-(5-Methyl-2-furyl)vinyl]-1Н-1,2,4-triazol-
5-yl}phenol (IIj) yellow crystals.
2-{1-[2-(Diethylamino)ethyl]-5-[2-phenylvinyl]-1Н-
1,2,4-triazol-3-yl}phenol hydrochloride (IIIa). To a
solution of 10 mmol of compound IIl in 15 ml of
acetone was added 20 mmol of NaOH and 10 mmol of
(2-chloroethyl)diethylamine hydrochloride. The reaction
mixture was boiled for 1.5 h, and water was poured to
it. The formed out oil was separated, dissolved in
20 ml of acetone and 6 ml of 7% HCl solution was
added to it. The product was kept for 12 h at room
temperature, then the precipitate formed was filtered
off and washed with water. Colorless crystals.
chloro-10-(chloroacetyl)-10Н-phenothiazine
was
added. The reaction mixture was refluxed for 1.5 h,
then diluted with water. The separated precipitate was
filtered off and washed with water. Light brown
crystals were obtained.
2-{1-[2-(2-Chloro-10Н-phenothiazin-10-yl)-2-oxo-
ethyl]-5-[2-(2-thienyl)vinyl]-1Н-1,2,4-triazol-3-yl}phe-
nol (IVb) was prepared similarly, brown crystals.
2- [5-[2-(4-Methoxyphenyl)vinyl]-1-(mopholin-4-
ylmethyl)-1Н-1,2,4-triazol-3-yl]phenol (Va). A mix-
ture containing 10 mmol of compound IIa, 20 ml of
benzene, 10 mmol of morpholine and 20 mmol of form-
Compounds IIIb–IIIh were prepared similarly.
2-(1-[2-(Diethylamino)ethyl]-5-{2-[4-(methoxy)-
phenyl]vinyl}-1Н-1,2,4-triazole-3-yl)phenol hydro-
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009

REACTIONS OF HYDROXYPHENYL-SUBSTITUTED 1,2,4-TRIAZOLES
2243
aldehyde was refluxed for 6 h. Then the solvent was
evaporated and the residue was crystallized to isolate
light brown crystals. C NMR spectrum (acetone-d6),
5-[2-(3,4-dimethoxyphenyl)vinyl]-3-(2-hydroxy-
phenyl)-N,N-dimethyl-1Н-1,2,4-triazol-1-sulfonamide
(VIIc), beige crystals.
13
δ, ppm, J, Hz: 48.9 t (2C, Cmorph, J = 138.1), 51.1 q
3-(2-Hydroxyphenyl)-N,N-dimethyl-5-{2-[4-(me-
thylthio)phenyl]vinyl}-1Н-1,2,4-triazol-1-sulfonamide
(VIId), yellow crystals.
(1C, CН3, J = 144.4), 53.2 t (1C, CН2,
J = 143.0),
69.55 m (2C, CН2, J = 152.8), 108.3 m (1C, Car), 115.1
m (1C, Cvinyl), 117.6 m (2C, Car), 118.7 m (1C, Car),
120 t (1C, Car, J = 6.3), 127 d (1C, Car, J = 7.0), 128.3
m (2C, Car), 128.8 t (1C, Car, J = 7.3), 131.4 t (1C, Car,
ACKNOWLEDGMENTS
J = 5.3), 139.8 m (1C, Cvinyl), 154.25 m (1C, Ctriazole
,
3
2J = 5.0, J = 2.6), 157 m (1C, Car), 158 m (1C, Car),
This work was financially support by the grants
RNP 2.2.1/2371 and 2.2.1.1/2348.
160.2 d (1C, Ctriazole, J = 4.5).
2-[5-[2-(3,4-dimethoxyphenyl)vinyl]-1-morpholin-
4-ylmethyl)-1Н-1,2,4-triazol-3-yl]phenol (Vb), beige
crystals.
REFERENCES
1. Shering, A.G., FRG Patent no. 2936951, 1981;
2-{5-Methyl-1-[(4-methylphenyl)sulfonyl]-1Н-1,2,4-
triazol-3-yl}phenol (VIa). To a solution of 10 mmol
of compound IIk in 3.5 ml of pyridine was added
10 mmol of TsCl. The reaction mixture was heated to
boiling, then cooled, and left standing for 24 h, and
then water was poured to it. The precipitate formed
was filtered off and washed with water. Colorless
crystals formed.
Chem.Abstrs., 1982, vol. 96, p. 52509.
2. Bayer A.G., FRG Patent no. 2936951, 1975; Chem.
Abstrs., 1975, vol. 83, p. 206290.
3. Ryabukhin, Yu.I., Doctoral Sci. (Chem.) Dissertation,
Nauk. Rostov-on-Don, 1991.
4. Ryabukhin, Yu.I., Mezheritskii, V.V., Karpenko, V.D.,
and Dorofeenko, G.N., Khim. Geterotsikl. Soed., 1975,
no. 9, p. 1184.
Compounds VIb–VId were prepared similarly.
5. Dorofeenko, G.N., Ryabukhin, Yu.I., Bulgarevich, S.B.,
Mezheritskii, V.V., and Ryabukhina, O.Yu., Zh. Org.
Khim., 1977, vol. 13, no. 11, p. 2459.
2-{1-[(4-Methylphenyl)sulfonyl]-5-[2-phenylvinyl]-
1Н-1,2,4-triazol-3-yl}phenol (VIb), colorless crystals.
6. Suvorova, E.Yu., Vikrishchuk, N.I., Popov, L.D.,
Starikova, Z.A., Vikrishchuk, A.D., and Zhdanov, Yu.A.,
Zh. Org. Khim., 2007, vol. 43, no. 10, p. 1556.
2-{5-[2-(3,4-dimethoxyphenyl)vinyl]-1-[(4-methyl-
phenyl)sulfonyl]-1Н-1,2,4-triazol-3-yl}phenol (VIc),
light-brown crystals.
7. Kompan, O.E., Gerr, R.G., Struchkov, Yu.T., Falee-
va, L.N., Ryabukhin, Yu.I., Olekhnovich, L.P., Khim.
Geterotsikl. Soed ,1989, no. 1, p. 109.
2-{5-[2-(4-Bromophenyl)vinyl]-1-[(4-methylphe-
nyl)sulfonyl]-1Н-1,2,4-triazol-3-yl}phenol (VId), color-
less crystals.
8. Emsli, D., Finei, D., and Satklif, L., Spektroskopiya
3-(2-Hydroxyphenyl)-N,N,5-trimethyl-1Н-1,2,4-
triazol-1-sulfonamide (VIIa). To a solution of 10 mmol
of compound IIk in 3.5 ml of pyridine was added
10 mmol of dimethylsulfamoyl chloride. The reaction
mixture was heated to boiling, cooled, and kept for
24 h at a room temperature, and then 12 ml of water
was poured to it. The separated crystals were filtered
off, washed with water, and the colorless crystals were
collected.
yadernogo
magnitnogo
rezonansa
vysokogo
razresheniya (High Resolution NMR Spectroscopy),
Moscow: Mir, 1968, p. 514.
9. Mashkovskii, M.D., Lekarstvennye sredstva (Renedies),
Moscow: Meditsina, 1972, p. 368.
10. Fukuzumi, K., Ikeda, N., and Egawa, M., J. Am. Oil
Chem. Soc. 1976, vol. 53, p. 623.
11. Nagy, S., Argyclan, G., Molnar, J., Kawase, M., and
Motohashi, N., Anticancer Res., 1996, vol. 16, p. 1916.
Compounds VIIb–VIId were prepatred similarly.
12. Moosman, B., Skutella, T., Beyer, K., and Behl, C.,
Biol. Chem., 2001, vol. 382, p. 1601.
3-(2-Hydroxyphenyl)-N,N-dimethyl-5-[2-phenyl-
vinyl]-1Н-1,2,4-triazol-1-sulfonamide (VIIb), color-
less crystals.
13. Korth, C., May, B., Cohen, F.E., and Prusiner, S.B.,
Proc. Natl. Acad. Sci. U. S., 2001, vol. 98, p. 9836.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 79 No. 10 2009