Synthesis of 4′-[3-methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl]- 2′,5′-diphenyl-2′,4′-dihydro spiro[indolin-3,3′[1, 2,4]triazol]-2-one derivatives

Article abstract of DOI:10.1134/S107036321403030X

In this paper 1,3-dipolar cycloaddition reaction has been studied. An efficient synthesis of 4′-[3-methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl]- 2′,5′-diphenyl-2′,4′-dihydro spiro(indolin-3,3′[1, 2,4]triazol)-2-one derivatives using triethylamine in MeCN at room temperature is reported. The structures of the obtained compounds were confirmed by means of elemental analysis, MS and spectral (IR, ¹H, and ¹³C NMR) methods.

Full text of DOI:10.1134/S107036321403030X

ISSN 1070-3632, Russian Journal of General Chemistry, 2014, Vol. 84, No. 3, pp. 586–592. © Pleiades Publishing, Ltd., 2014.
Synthesis of 4'-[3-Methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl]-
2',5'-diphenyl-2',4'-dihydro Spiro[indolin-3,3'[1,2,4]triazol]-2-one
Derivatives1
Atiye Bazian, Milad Taheri, and Haniyeh Alavi
Department of Chemistry, Islamic Azad University, Shahre-rey Branch, Tehran, Iran
e-mail: Miladtaheri1@hotmail.co.uk, m.taheri2011@gmail.com
Received September 23, 2013
Abstract―In this paper 1,3-dipolar cycloaddition reaction has been studied. An efficient synthesis of 4'-[3-
methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl]-2',5'-diphenyl-2',4'-dihydro spiro(indolin-3,3'[1,2,4]triazol)-2-one
derivatives using triethylamine in MeCN at room temperature is reported. The structures of the obtained
compounds were confirmed by means of elemental analysis, MS and spectral (IR, 1H, and 13C NMR) methods.
DOI: 10.1134/S107036321403030X
INTRODUCTION
EXPERIMENTAL
Chemistry of nitril imines has been developing for
more than forty years already. Because of their
chemical activity and readiness to undergo
cycloaddition reaction with different substances they
found important usage for preparation of substantial
raw material [1–5]. Hidrazonyl halides are most usual
starting materials used for preparation of nitril amines.
Final cyclization step to form spiro structure is
accomplished with a suitable base, such as triethyl
amine. Mechanism of this reaction has been reported
by Shavali [6–10]. Indol core of isatin has been long
known for different biological activities, like anti-
microbial anti-mold, anti-cancer [11–19]. Among these
heterocycles, spiro indoles have been identified as
privileged structures in medicinal chemistry and have
attracted increasing interest in the recent years [20–
22]. Considering the above reasons, the development
of new and simple synthetic method for the efficient
preparation of spiro indole heterocycles containing
1,2,4-triazol ring fragments is therefore an interesting
challenge. We studied the reaction of isatin imine and
(Z)-1-[chloro (phenyl) methylene]-2-phenylhydrazine
in the presence of triethyl amine in MeCN at room
temperature. The reaction was complete after 18–21 h
(reaction progress was monitored by TLC) and 4'-[3-
methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl]-2',5'-diphe-
nyl-2',4'-dihydro spiro(indolin-3,3'[1,2,4]triazol)-2-one
derivatives were obtained in 75–95% yield.
All reagents used in this research were GR grade
and all solvents were redistilled before use. Merk thin
layer chromatography sheets Art no: 1 : 0554 were used
for TLC. NMR spectra were recorded on an JEOL
DELTA NMR 400 MHz (1H NMR) and 100 MHz (13C
NMR) instruments, using CDCl3 and DMSO-d6 as
solvent. IR spectra were recorded on a Perkin-Elmer
model 1420 spectrophotometer.
Thiocarbonohydrazide was prepared from hyd-
razine hydrate and carbon disulfide in 89% yield.
White crystals, mp, °C: 195–197; IR (KBr): 3461,
1
3272, 3204, 1300; H NMR (400 MHz, CDCl3), δ,
13
ppm: 2 d (2H), 2.01–2.03 d (J = 2 and 8 Hz, 4H); C
NMR (CDCl3), δ, ppm: 186; MS, m/z; 106 (M+, 92.16);
Calculated, %: C 11.31; H 5.70; N 52.78; S 30.21.
CH4N4S. Found, %: C 11.28; H 5.32; N 52.80; S 30.20.
N'-Phenylbenzohydrazide was prepared from 15 g
of phenyl hydrazine and 19 g of benzoyl chloride in
pyridine in 77% yield. White crystals; mp, °C: 202–
204; IR (KBr): 3324, 3269, 3054, 1644; 1H NMR (400
MHz, CDCl3), δ, ppm: 4.01 d (1H), 6.66 m (1H), 7.18
q (2H), 7.44–7.46 m (J = 2 and 8 Hz, 2H), 7.51 t (1H),
7.95 m (2H), 8.00 m (1H); 13C NMR (CDCl3), δ, ppm:
113.2, 127.5, 128.9, 129.3, 132.2, 134.1, 151.5, 164.9;
MS, m/z: 212 (M+, 90.10); Calculated, %: C 73.56; H
5.70; N 13.20; O 7.54. C13H12N2O. Found, %: C 73.52;
H 5.72; N 13.18; O 7.50.
4-Amino-3-methyl-1H-1,2,4-triazol-5-thione (I).
Thiocarbohydrazide, 2 g, and acetic acid, 16 mL, were
1 The text was submitted by the authors in English.
586

SYNTHESIS OF 4'-[3-METHYL-5-THIOXO-1H-1,2,4-TRIAZOL-4(5H)-YL]-...
587
placed in a flask and heated on an oil bath to 120°C for
20 min to form clear solution that after 5 min suddenly
started to form deposit. After heating for further
15 min the reaction mixture was cooled on an ice bath.
Solid crystalline product was collected by filtration to
give 1.08 g (91% yield) as white crystals; mp, °C:
198–201; IR (KBr): 3112, 2946, 1628, 1318; 1H NMR
(400 MHz, CDCl3), δ, ppm: 0.9 s (3H), 2.00 d (2H),
7.01 d (1H); 13C NMR (CDCl3), δ, ppm: 22.7, 155,
186; MS, m/z: 130 (M+, 85.00); Calculated, %: C
27.68; H 4.65; N 43.04; S 24.63. C3H6N4S. Found, %:
C 27.60; H 4.62; N 43.01; S 24.62.
(J = 2 and 8 Hz, 2H), 7.43–7.45 d (2H), 7.89 d (2H),
8.01 s (1H); C NMR (CDCl3), δ, ppm: 113.9, 119.2,
128.9, 129.00, 129.3, 132.3, 137.7, 151.1, 164.9; MS,
m/z: 246 (M+, 85.13); Anal. Calculated, %: C 63.29; H
4.49; Cl 14.37; N 11.36; O 6.49. C13H11ClN2O. Found,
%: C 63.30; H 4.46; Cl 14.33; N 11.35; O 6.51.
13
(Z)-1-[Chloro(4-chlorophenyl)methylene]-2-phe-
nylhydrazine (V). Prepared similarly to phenyl-
hydrazine III from 4-chloro-N'-phenylbenzohydrazide
IV in 64% yield. white crystals; mp, °C: 251–253; IR
1
(KBr): 3308, 3053, 1649, 753; H NMR (400 MHz,
CDCl3), δ, ppm: 6.46 q (2H), 6.62 q (1H), 7.00 m
(1H), 7.01–7.03 t (J = 2 and 8 Hz, 2H), 7.3 q (2H), 7.6
t (2H); 13C NMR (CDCl3), δ, ppm: 116.3, 118.8, 127.7,
129.00, 129.6, 130.6, 136.6, 143.1, 155.1; MS, m/z:
264 (M+, 85.20); Calculated, %: C 58.89; H 3.80; Cl
26.74; N 10.57. C13H10Cl2N2. Found, %: C 58.85; H
3.79; Cl 26.75; N 10.52.
(3Z)-3-[3-Methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-
ylimino]indolin-2-one (II). 1H-amino-3-methyl-1H-
1,2,4-triazol-5-tion, 0.390 g, and isatin, 0.441g were
mixed with 20 mL of acetonitrile and 20 drops of
acetic acid, heated for 5 hours and kept for 1 day at
room temperature. Crystalline deposit formed was
washed with ethanol to give II in 89% yield as yellow
crystals; mp, °C: 234–236; IR (KBr): 3254, 2925,
1752; 1H NMR (400 MHz, CDCl3), δ, ppm: 0.9 s (3H),
7.00 m (1H), 7.01 t (1H), 7.30 t (1H), 7.60–7.70 m
(J = 2 and 8 Hz, 2H), 8.00 s (1H); 13C NMR (CDCl3),
δ, ppm: 23.2, 117.8, 121.7, 124.5, 129.4, 131.3, 132.9,
146.8, 155.00, 167.5, 186; MS, m/z: 259 (M+, 76.53);
Calculated, %: C 50.95; H 3.50; N 27.01; O 6.17; S
12.37. C11H9N5OS. Found, %: C 50.93; H 3.49; N
26.95; O 6.14; S 12.35.
3,5-Dinitro-N'-phenylbenzohydrazide
(VI).
Prepared similarly to N'-phenylbenzohydrazide in 72%
yield. silver crystals; mp, °C: 243–245; IR (KBr):
1
3281, 3094, 1648, 1541, 1345; H NMR (400 MHz,
CDCl3), δ, ppm: 4.01 s (1H), 6.66 m (2H), 6.71 m
(1H), 7.17–7.19 t (J = 2 and 8 Hz, 2H), 8.00–8.02 s
13
(1H), 9.27 d (2H), 9.37 d (1H); C NMR (CDCl3), δ,
ppm: 113.2, 119.2, 122.1, 128.5, 129.3, 136.00, 149.4,
151.00, 164.9; MS, m/z: 302 (M+, 95.16); Calculated,
%: C 51.66; H 3.33; N 18.54; O 26.47. C13H10N4O5.
Found, %: C 51.64; H 3.30; N 18.53; O 26.45.
(Z)-1-[Chloro(phenyl)methylene]-2-phenylhyd-
razine (III). Triphenyl phosphine, 1.55 g, and N'-
phenylbenzohydrazide, 4.24 g, were mixed in a beaker
with 40 mL of acetonitril at room temperature. After
30 min 1.95 mL of carbon tetrachloride were added
slowly over 2 h to the suspension. The reaction
continued for 20 h, then the beaker was placed on an
ice bath for 30 min. Solid deposit was filtered off to
give III as white crystals in 69% yield; mp, °C: 240–
(Z)-1-[Chloro(3,5-dinitrophenyl)methylene]-2-
phenylhydrazine (VII). Prepared similarly to phenyl-
hydrazine III from 3,5-dinitro-N'-phenylbenzo-
hydrazide VI in 66% yield. silver crystals; mp, °C:
1
250–252; IR (KBr): 3296, 3096, 1539, 1345, 725; H
NMR (400 MHz, CDCl3), δ, ppm: 6.46 d (2H), 6.62 m
(1H), 7.00 m (1H), 7.01 m (J = 2 and 8 Hz, 2H), 8.89–
8.91 d (2H), 9.1 d (1H); 13C NMR (CDCl3), δ, ppm:
116.3, 118.7, 121.00, 129.6, 130.2, 131.4, 143.1,
149.4, 155; MS, m/z: 320 (M+, 100.00); Calculated, %:
C 48.69; H 2.83; Cl 11.06; N 17.47; O 19.96.
C13H9ClN4O4. Found, %: C 48.67; H 2.82; Cl 11.01; N
17.42; O 19.93.
1
243; IR (KBr): 3304, 3051, 1598, 752; H NMR (400
MHz, CDCl3), δ, ppm: 6.46 t (2H), 6.62 t (1H), 7.00 m
(1H), 7.02–7.04 m (J = 2 and 8 Hz, 2H), 7.30 d (3H),
13
7.60 q (2H); C NMR (CDCl3), δ, ppm: 116.3, 118.4,
128.9, 129.4, 131.2, 143.3, 155.00; MS, m/z: 230 (M+,
65.56). Calculated, %: C 67.68; H 4.81; Cl 15.37; N
12.14. C13H11ClN2. Found, %: C 67.62; H 4.78; Cl
15.32; N 12.20.
4'-[3-Methyl-5-thioxo-1H-1,2,4-triazol-4(5H)-yl]-
2',5'-diphenyl-2',4'-dihydro spiro(indolin-3,3'[1,2,4]-
triazol)-2-one (VIII). 1-(Chloro(phenyl)methylene)-2-
phenyl hydrazine III, 0.07 g, and 3-[3-methyl-5-
thioxo-1H-1,2,4-triazol-4(5H)-ylimino]indolin-2-one
II, 0.08 g, were added to a mixture of 1 mL of triethyl
amine and 4 mL of acetonitrile in a beaker at room
4-Chloro-N'-phenylbenzohydrazide (IV). Prepared
similarly to N'-phenylbenzohydrazide in 70% yield.
white crystals; mp, °C: 242–246; IR (KBr): 3347,
3237, 3054, 1648, 1095; 1H NMR (400 MHz, CDCl3),
δ, ppm: 4.00 d (1H), 6.66 m (2H), 6.71 m (1H), 7.18 d
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014

588
ATIYE BAZIAN et al.
mp, °C: 285–288; IR (KBr): 3250, 3205, 1782, 1630;
S
Cl
C
1H NMR (400 MHz, CDCl3), δ, ppm: 0.9 s (3H), 2.35 s
(3H), 6.43 m (2H), 6.57–6.59 (J = 2 and 8 Hz, m, 1H),
6.88 t (1H), 7.00 m (1H), 7.04–7.05 m (4H), 7.12 m
(2H), 7.50–7.52 d (2H), 8.00 s (1H); 13C NMR
(CDCl3), δ, ppm: 23.00, 24.3, 113.5, 117.2, 124.9,
125.1, 125.7, 127.3, 129.9, 130.6, 139.8, 141.5, 143.6,
155.05, 158.3, 185.00; MS, m/z: 467 (M+, 91.85);
Calculated, %: C 64.22; H 4.53; N 20.97; O 3.42; S
6.86. C25H21N7OS. Found, %: C 64.21; H 4.50 N
20.96; O 3.43; S 6.84.
H
N
N
N
HN
+
N
NH
O
CH3
N
S
CH3CN/Et3N
N
N
O
HN
N
5'-(4-Methoxyphenyl)-4'-[3-methyl-5-thioxo-1H-
1,2,4-triazol-4(5H)-yl]-2',5'-diphenyl-2',4'-dihydro
spiro(indolin-3,3'[1,2,4]triazol)-2-one (XI). Prepared
similarly to product VIII from corresponding 4-
methoxyphenyl derivative in 92% yield. White crys-
tals; mp, °C: 288–291; IR (KBr): 3310, 2992, 1783,
1640; 1H NMR (400 MHz, CDCl3), δ, ppm: 0.9 s (3H),
3.73 s (3H), 6.45 t (2H), 6.55–6.58 m (J = 2 and 8 Hz,
1H), 6.80–6.82 m (2H), 6.88 m (1H), 7.02 m (1H),
7.05–7.07m (4H), 7.50–7.52 t (3H), 8.00 s (1H); 13C
NMR (CDCl3), δ, ppm: 22.95, 55.9, 87.00, 113.8,
114.2, 117.5, 121.3, 122.4, 124.9, 127.5, 129.7, 131.00,
141.2, 143.8, 155.1, 168.2, 186.00; MS, m/z: 191 (M+,
92.16); Calculated, %: C 62.10; H 4.38; N 20.28;
O 6.62; S 6.63. C25H21N2O2S. Found, %: C 62.12; H
4.36 N 20.20; O 6.61; S 6.60.
N
N
H
CH3
Synthetic route for the 4'-[3-methyl-5-thioxo-1H-1,2,4-triazol-
4(5H)-yl]-2',5'-diphenyl-2',4'-dihydro spiro(indolin-3,3'-
[1,2,4]triazol)-2-one derivatives.
temperature. Yield 89%; orange crystals; mp, °C: 301–
303; IR (KBr): 3285, 3000, 1747, 1608; H NMR
1
(400 MHz, CDCl3), δ, ppm: 0.9 s (3H), 6.43 m (2H),
6.58 m (1H), 6.88 m (J = 2 and 8 Hz, 1H), 7.00 m
(1H), 7.04–7.05 m (4H), 7.30 d (3H), 7.52 t (1H), 7.60
d (2H), 8.01 s (1H); 13C NMR (CDCl3), δ, ppm: 23.00,
87.1, 113.5, 117.2, 122.1, 124.9, 125.1, 127.9, 128.7,
129.9, 130.2, 131.1, 141.2, 143.8, 155.00, 158.2,
185.01; MS, m/z: 453 (M+, 91.10); Calculated, %: C
63.56; H 4.22; N 21.62; O 3.53; S 7.07. C24H19N7OS.
Found, %: C 63.52; H 4.20; N 21.61; O 3.52; S 7.01
5'-(4-Hydroxyphenyl)-4'-[3-methyl-5-thioxo-1H-
1,2,4-triazol-4(5H)-yl]-2',5'-diphenyl-2',4'-dihydro
spiro(indolin-3,3'[1,2,4]triazol)-2-one (XII). Prepared
similarly to product VIII from corresponding 4-hyd-
roxyphenyl derivative in 75% yield. Black crystals;
mp, °C: 298–301; IR (KBr): 3295, 3195, 1742, 1650;
1H NMR (400 MHz, CDCl3), δ, ppm: 0.9 s (3H), 5.00 s
(1H), 6.43 t (2H), 6.56–6.58 m (J = 2 and 8 Hz, 1H),
6.79–6.81 t (2H), 6.88 t (1H), 7.00 m (1H), 7.04–7.05
m (4H), 7.40 d (2H), 7.50–7.52 d (1H), 8.01 s (1H);
13C NMR (CDCl3), δ, ppm: 23.00, 87.03, 113.5, 116.2,
117.2, 121.3, 122.1, 124.7, 127.6, 129.5, 130.7, 141.5,
143.8, 155.00, 159.9, 168.2, 186.1; MS, m/z: 469 (M+,
98.10); Calculated, %: C 61.39; H 4.08; N 20.88; O
6.82; S 6.83. C24H19N7O2S. Found, %: C 61.37; H 4.02
N 20.84; O 6.80; S 6.81.
5'-(4-Aminophenyl)-4'-[3-methyl-5-thioxo-1H-
1,2,4-triazol-4(5H)-yl]-2',5'-diphenyl-2',4'-dihydro
spiro(indolin-3,3'[1,2,4]triazol)-2-one (IX). Prepared
similarly to product VIII from corresponding 4-
aminophenyl derivative in 76% yield. Brown crystals;
mp, °C: 293–296; IR (KBr): 3292, 3150, 1752, 1610;
1H NMR (400 MHz, CDCl3), δ, ppm: 0.9 s (3H), 4.5 d
(2H), 6.43 m (2H), 6.50 m (J = 2 and 8 Hz, 2H), 6.58
m (1H), 7.00 m (1H), 7.04–7.05 m (4H), 7.42 d (2H),
7.52 t (1H), 8.00 s (1H); 13C NMR (CDCl3), δ, ppm:
23.01, 87.3, 113.5, 115.4, 117.5, 118.7, 122.1, 122.9,
125.9, 127.7, 129.7, 130.7, 141.2, 143.8, 155.00,
158.2, 185.01; MS, m/z: 468 (M+, 98.58); Calculated,
%: C 61.52; H 4.30; N 23.92; O 3.41; S 6.84.
C24H20N8OS. Found, %: C 61.50; H 4.29; N 23.91; O
3.42; S 6.81.
5'-(4-Iodophenyl)-4'-[3-methyl-5-thioxo-1H-1,2,4-
triazol-4(5H)-yl]-2',5'-diphenyl-2',4'-dihydro spiro-
(indolin-3,3'[1,2,4]triazol)-2-one (XIII). Prepared
similarly to product VIII from corresponding 4-
iodophenyl derivative in 83% yield. Yellow crystals;
mp, °C: 284–286; IR (KBr): 3155, 3100, 1723, 1670;
5'-(4-Methylphenyl)-4'-[3-methyl-5-thioxo-1H-
1,2,4-triazol-4(5H)-yl]-2',5'-diphenyl-2',4'-dihydro
spiro(indolin-3,3'[1,2,4]triazol)-2-one (X). Prepared
similarly to product VIII from corresponding 4-
methylphenyl derivative in 85% yield. White crystals;
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014

SYNTHESIS OF 4'-[3-METHYL-5-THIOXO-1H-1,2,4-TRIAZOL-4(5H)-YL]-...
Yields and reaction conditions of the synthesized compounds
589
Comp. no.
Product
Color
White
Reaction time, h
40
Yield, %a
91
mp, °C
201
235
I
S
NH2
N
HN
N
N
CH3
S
H
Yellow
20
89
II
N
N
N
H3C
O
N
H
Cl
C
White
White
4
69
70
240
245
III
IV
H
N
N
Cl
Cl
20
H
N
C
N
H
O
White
Silver
20
20
64
72
252
243
V
N
C
N
H
Cl
NO2
VI
H
N
O2N
C
N
H
O
NO2
Silver
21
18
66
89
252
303
VII
N
O2N
C
N
H
Cl
Orange
VIII
N
S
N
N
HN
N
O
N
N
H
CH3
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014

590
ATIYE BAZIAN et al.
Table (Contd.)
Comp.
no.
Product
Color
Reaction time, h
20
Yield, %a
76
mp, °C
295
Brown
IX
H2N
N
S
N
N
O
HN
N
N
N
H
CH3
H3C
White
19
85
285
X
N
S
N
N
HN
N
N
O
N
H
CH3
H3CO
White
17
92
290
XI
N
S
N
N
HN
N
N
O
N
H
CH3
Black
18
75
300
XII
HO
N
S
N
N
HN
N
N
O
N
H
CH3
Yellow
20
83
285
XIII
I
N
S
N
N
HN
N
N
O
N
H
CH3
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014

SYNTHESIS OF 4'-[3-METHYL-5-THIOXO-1H-1,2,4-TRIAZOL-4(5H)-YL]-...
591
Table (Contd.)
Comp.
no.
Product
Color
White
Reaction time, h
21
Yield, %a
76
mp, °C
302
XIV
OEt
N
S
N
N
HN
N
N
O
N
H
CH3
a Yields refer to isolated and purified products.
1H NMR (400 MHz, CDCl3), δ, ppm: 0.9 s (3H), 6.43 t
(2H), 6.58 m (1H), 6.85–6.88 t (J = 2 and 8 Hz, 1H),
7.00–7.02 m (1H), 7.04–7.06 m (4H), 7.42 d (2H),
7.54 d (1H), 7.70 t (2H), 8.00 s (1H); 13C NMR
(CDCl3), δ, ppm: 23.03, 87.00, 95.8, 113.4, 117.2,
122.2, 124.9, 127.6, 129.9, 130.6, 137.5, 141.2, 143.8,
155.00, 168.25, 186.00; MS, m/z: 579 (M+, 92.89);
Calculated, %: C 49.75; H 3.13;I, 21.90 N 16.92; O
2.76; S 5.53. C24H18IN7O2S. Found, %: C 49.73; H
3.09; I, 21.87 N 16.90; O 2.80; S 5.50.
process and obtained results are shown in the table and
the figure.
ACKNOWLEDGMENTS
We thank Islamic Azad University, Shahre-rey
Branch for its technical support in IR spectroscopy of
the synthesized products.
REFERENCES
1. Shawali, A.S. and Edrees, M.M., Arkivoc., 2006,
5'-(4-Ethoxyphenyl)-4'-[3-methyl-5-thioxo-1H-1,2,4-
triazol-4(5H)-yl]-2',5'-diphenyl-2',4'-dihydro spiro-
(indolin-3,3'[1,2,4]triazol)-2-one (XIV). Prepared
similarly to product VIII from corresponding 4-ethoxy-
phenyl derivative in 76% yield. White crystals; mp,
pp. 292–365.
2. Shawali, A.S. and Albar, H.A., Can. J. Chem., 1986,
vol. 64, pp. 871–875.
3. Shawali, A.S., Abdelkhalik, A.A., and Sayed, A.R.,
J. Chin. Chem. Soc., 2001, vol. 48, p. 693.
1
°C: 300–302; IR (KBr): 3320, 3152, 1743, 1650; H
4. Shawali, A.S. and Parkanyi, C., J. Heterocyclic. Chem.,
NMR (400 MHz, CDCl3), δ, ppm: 0.9 s (3H), 1.33 t
(3H), 3.98 m (2H), 6.43 t (2H), 6.56–6.58 m (J = 2 and
8 Hz, 1H), 6.80 d (2H), 6.88 t (1H), 7.01 m (1H),
1980, vol. 17, pp. 833–854.
5. Shawali, A.S., Heterocycles., 1983, vol. 20, pp. 2239–
13
2285.
7.04–7.05 m (4H), 7.50–7.52 d (3H), 8.00 s (1H); C
6. Shawali, A.S., Chem. Rev., 1993, vol. 93, pp. 2731–
NMR (CDCl3), δ, ppm: 14.8, 23.01, 64.7, 87.02, 113.5,
114.5, 117.2, 120.3, 122.1, 124.9, 126.7, 127.9, 129.9,
130.7, 141.5, 143.8, 155.02, 158.2, 168.2, 186.00; MS,
m/z: 497 (M+, 99.54); Calculated, %: C 62.76; H 4.66;
N 19.71; O 6.43; S 6.44. C26H23N7O2S. Found, %: C
62.75; H 4.68 N 19.70; O 6.41; S 6.42.
2777.
7. Shawali, A.S. and Abdallah, M.A., Adv. Heterocycl.
Chem., 1995, vol. 63, pp. 277–338.
8. Shawali, A.S. and Mosselhi, M.A.N., J. Heterocycl.
Chem., 2003, vol. 40, pp. 725–746.
9. Bekircan, O., Kahveci, B., and Kucuk, M., Tur. J.
Chem., 2006, vol. 30, pp. 29–40.
RESULTS AND DISCUSSION
10. Kahveci, B., Bekircan, O., and Karaoglu, S.A., Indian.
J. Chem., 2005, vol. 44B, pp. 2614–2617.
Structures of all synthesized compounds in table
1
were confirmed on the basis of their H NMR, 13C
12. Singh, G.S., Singh, T., and Lakhan, R., Indian J. Chem.,
NMR, and IR spectral data as well as MS and
elemental analyses. In 13C NMR spectrum, specific
tertiary carbon pick appears at about 90 ppm. Total
1997, vol. 36B, pp. 951–954.
13. Kahveci, B., Molecules, 2005, vol. 10, pp. 376–382.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014

592
ATIYE BAZIAN et al.
14. Escobar-Valderrama, J.L., Can. J. Chem., 1989, vol. 67(2),
chemie, 2007, vol. 138, pp. 771–776.
pp. 198–201.
19. Kahveci, B. and Ikizler, A.A., Acta. Polon. Pharm-
Drug. Res., 2000, vol. 57, pp. 119–122.
15. Bekircan, O. and Bektas, H., Molecules., 2008, vol. 13,
pp. 2126–2135.
20. Wolf, M. and Masciffi, A.A., US Patent, 1965, 395.156;
16. Ashok, K. Sen., Noren, and Singh, R., J. Mol. Struc.,
Chem. Abstr., 1988, vol. 69, 96504r.
1998, vol. 470, pp. 61–69.
21. Winters, G. and Mola, N.D., German Patent, 1975,
17. Ewiss, N.F., Bahajaj, A.A., and Elsherbini, E.A., J. Hetero-
cycl. Chem., 1986, vol. 23, pp. 1451–1458.
DE2.442.667; Chem. Abstr., 1975, vol. 83, 28096.
22. Corent, M.J. and Thio, A.P., J. Med. Chem., 1976,
18. Abdel-latif, E. and Metwally, M., Monatshefte fur
vol. 19, p. 892.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 3 2014