Cyclodesulfurization of Substituted Thiosemicarbazides into 1,3,4-Oxadiazoles via Hydrazonoyl Chlorides

Article abstract of DOI:10.1080/10426507.2013.858252

The reaction of thiosemicarbazides 1a-h with hydrazonoyl chlorides 2a-g at ambient temperature, in the presence of triethylamine yielded, in each case, two products. The structure of these compounds was confirmed as 1,3,4-oxadiazoles 14a-h and hydrazonoth

Full text of DOI:10.1080/10426507.2013.858252

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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Cyclodesulfurization of Substituted
Thiosemicarbazides into 1,3,4-
Oxadiazoles via Hydrazonoyl Chlorides
Hatem A. Abdel-Azizab, Mashooq A. Bhata & Mohamed Ghazzalic
a Department of Pharmaceutical Chemistry, College of Pharmacy,
King Saud University, Riyadh 11451, Kingdom of Saudi Arabia
b Department of Applied Organic Chemistry, National Research
Center, Dokki, Cairo 12622, Egypt
c Department of Chemistry, College of Science, King Saud University,
Riyadh 11451, Saudi Arabia
Accepted author version posted online: 26 Feb 2014.Published
online: 12 Aug 2014.
To cite this article: Hatem A. Abdel-Aziz, Mashooq A. Bhat & Mohamed Ghazzali (2014)
Cyclodesulfurization of Substituted Thiosemicarbazides into 1,3,4-Oxadiazoles via Hydrazonoyl
Chlorides, Phosphorus, Sulfur, and Silicon and the Related Elements, 189:9, 1328-1336, DOI:
10.1080/10426507.2013.858252
To link to this article: http://dx.doi.org/10.1080/10426507.2013.858252
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Phosphorus, Sulfur, and Silicon, 189:1328–1336, 2014
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2013.858252
CYCLODESULFURIZATION OF SUBSTITUTED
THIOSEMICARBAZIDES INTO 1,3,4-OXADIAZOLES
VIA HYDRAZONOYL CHLORIDES
Hatem A. Abdel-Aziz,1,2 Mashooq A. Bhat,1
and Mohamed Ghazzali3
1Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud
University, Riyadh 11451, Kingdom of Saudi Arabia
2Department of Applied Organic Chemistry, National Research Center, Dokki,
Cairo 12622, Egypt
3Department of Chemistry, College of Science, King Saud University, Riyadh
11451, Saudi Arabia
GRAPHICAL ABSTRACT
Ar2
HN
O
Cl
N
R
H
N
H
N
N
N
H
N
Ar1
2
+
Ar1
Ar
N
H
+
Ar
R
N
Ar2
N
H
R
S
N
O
14a-h
S
1a-h
2a-g
15a-g
HN
2 B
2 B.HCl
Ar2
Abstract The reaction of thiosemicarbazides 1a–h with hydrazonoyl chlorides 2a–g at ambient
temperature, in the presence of triethylamine yielded, in each case, two products. The structure
of these compounds was confirmed as 1,3,4-oxadiazoles 14a–h and hydrazonothioates 15a–g.
The structure of 15b was confirmed through single crystal X-ray diffraction. A mechanism was
proposed for this cyclodesulfurization reaction.
Keywords Cyclodesulfurization; thiosemicarbazides; 1,3,4-oxadiazoles; hydrazonoyl chlo-
rides
INTRODUCTION
Thiosemicarbazides 1 (Figure 1) are useful intermediates in the synthesis of sev-
eral heterocycles such as 1,3-thiazoles,1 1,3,4-oxadiazoles,2 1,2,4-triazoles,3 and 1,3,4-
thiadiazoles.4 A number of these heterocycles are important in pharmaceutical and medic-
inal applications, for example, the 1,3,4-oxadiazole moiety is the main scaffold in several
drugs like Isentress, Nesapidil, and Furamizole.5
Hydrazonoyl halides 2 (Figure 1) have been received much attention owing to their
synthetic potential in the construction of a huge series of products, and the varied biological
activity exhibited by a number of these products. As main contributors to this field, Shawali
Received 9 July 2013; accepted 16 October 2013.
Address correspondence to Hatem A. Abdel-Aziz, Department of Pharmaceutical Chemistry, College
of Pharmacy, King Saud University, P.O. Box. 2457, Riyadh 11451, Kingdom of Saudi Arabia. E-mail:
hatem 741@yahoo.com; hatem@ksu.edu.sa
Color versions of one or more of the figures in the article can be found online at www.tandfonline.com/gpss.
1328

CYCLODESULFURIZATION OF SUBSTITUTED THIOSEMICARBAZIDES
1329
Figure 1 Structure of compounds 1–8.
has reported 11 reviews on the reactivity and reactions of hydrazonoyl halides including
their reactions with thiol/thione compounds.6,7
The reaction of N’-phenylbenzohydrazonoyl chloride (2) (R = Ar2 = Ph) with 1,4-
diphenylthiosemicarbazide (3) in the presence of triethylamine resulted in the formation
of N-(3,5-diphenyl-1,3,4-thiadiazol-2(3H)-ylidene)aniline (4) (Figure 1) and phenylhy-
drazine, which acted as the eliminated deprotonating agent.8 On the other hand, the straight-
forward preparation of thiosemicarbazides 1 was reported by the reaction of acid hydrazides
with isothiocyanates and their reaction with halo derivatives 5 has been published to produce
1,3-thiazoles 6 (Figure 1).1,9,10
In continuation of our interest in the chemistry of hydrazonoyl chlorides,11–16 we
aimed to study the reaction of thiosemicarbazides 1 with hydrazonoyl chlorides 2. This
reaction did not afford the possible 1,3,4-thiadizoles 7 or 5-arylazo-1,3-thiazoles 8 (Fig-
ure 1) where hydrazonoyl chlorides 2 act as cyclodesulfurization agent for 1 to produce
the corresponding 1,3,4-oxadiazoles 14 (Scheme 1). However, the reported cyclization
protocols for thiosemicarbazides 1 into 1,3,4-oxadiazole 14 were extensively investigated
using several desulfurization reagents that include mercuric salts, lead oxide, I2/NaOH,
TsCl (p-toluenesulfonyl chloride), DCC (N,Nꢁ-dicyclohexylcarbodiimide), EDC (ethylene
dichloride), polymer-supported DCC, PS-carbodiimides, TBTU (O-(benzotriazol-1-yl)-
N,N,N’,N’-tetramethyluronium tetrafluoroborate), and hypervalent iodine (V).5,17 In the
light of above data, we investigated, in this work, the behavior of hydrazonoyl chlorides 2
toward thiosemicarbazides 1.
Ar2
HN
O
Cl
N
R
H
N
H
N
N
N
H
N
Ar1
2
+
Ar1
Ar
N
H
+
Ar
R
N
Ar2
N
H
R
S
N
O
14a-h
S
1a-h
2a-g
15a-g
HN
2 B
2 B.HCl
Ar2
Scheme 1 The reaction of thiosemicarbazides 1a–h with hydrazonoyl chlorides 2a–g.
RESULTS AND DISCUSSION
The role of base in reactions of 2 is to generate nitrilimines 10 via 1,3-elimination
reaction during dehydrohalogenation process (Figure 2).6 The reactions of nitrilimines 10

1330
H. A. ABDEL-AZIZ ET AL.
NH
S
N
SH
9B
9A
N
pathway A
10
pathway B
R
N
10
Ar2
N
N
HN
SH
N
N
S
S
N
Ar2
H
N
R
N
Ar2
R
Ar2
N
11
R
13
12
Figure 2 The reaction of nitrilimines 10 with tautomeric thiol/thione compounds 9A/9B.
with tautomeric thiol/thione compounds 9A/9B may proceed via two pathways: pathway
A, 1,3-addition reaction where C-SH tautomer 9A acts as a protic nucleophile to form
thiohydrazonate 11, or pathway B, 1,3-dipolar cycloaddition reaction where C S tautomer
9B acts as dipolarophile to give the spirocyclo adduct 12 (Figure 2). Both 11 and 12
usually undergo further in situ reactions according to their structures such as compound
13 (Figure 2). Some of the latter intermediates were isolated as final products in certain
reactions.18 In this work, we aimed to react the tautomeric thiol/thione thiosemicarbazides
1A/1B with base-generated nitrilimines 10 (Scheme 1).
Therefore, the reaction of thiosemicarbazide 1a (Ar = Ar1 = Ph) with 2-oxo-N-
arylpropanehydrazonoyl chlorides 2a–e in ethanol at ambient temperature, in the presence
of triethylamine yielded, in each case, two products as examined by thin layer chromatog-
raphy (TLC; n-hexane/AcOEt, 4:1, v:v) (Scheme 1, Table 1). The solvent was evaporated
and the residue treated with water. The fractional crystallization of the latter residue from
n-hexane separated these products as soluble/insoluble compounds. Alternatively, the latter
crude material has been separated by column chromatography (n-hexane/AcOEt, 4:1, v:v).
In each case, the n-hexane insoluble products exhibited identical physical properties
1
and spectroscopic data (IR, H, and 13C NMR). The elemental analysis and mass spectra
of these products are compatible with the same molecular formula C14H11N3O, which
proved the structure as N,5-diphenyl-1,3,4-oxadiazol-2-amine 14a for these compounds.
Next, we extended our investigations to react thiosemicarbazides 1b–h with 2-oxo-N-
phenylpropanehydrazonoyl chloride 2a (R = COMe, Ar2 = Ph) under the same conditions
(Scheme 1, Table 1) and two reaction products were isolated, in each case, following the
same work up. The n-hexane insoluble products were identified as 1,3,4-oxadiazoles 14b–h,
respectively.
On the other hand, n-hexane soluble products for the latter reaction showed dissimilar
1
1
physical properties and spectroscopic data (IR, H, and 13C NMR). H NMR of these
products appeared a singlet signal integer to six protons in the region δ 2.29–2.35 in addition
to D2O exchangeable in the region δ 11.01–11.23 due to two protons. However, X-ray

CYCLODESULFURIZATION OF SUBSTITUTED THIOSEMICARBAZIDES
1331
Table 1 The structure and yields of 1,3,4-oxadiazoles 14a–h and hydrazonothioates 15a–g
14
Ar
Ar1
Yield (%)
15
R
Ar2
Yield (%)
14a
Ph
Ph
74
75
66
68
67
62
60
75
74
66
70
65
76
67
15a
15b
15c
15d
15e
15f
15g
15a
15a
15a
15a
15a
15a
15a
COMe
COMe
COMe
COMe
COMe
COOEt
Ph
COMe
COMe
COMe
COMe
COMe
COMe
COMe
Ph
49
40
47
45
39
43
40
48
41
45
47
39
43
38
2-MeC6H4
4-BrC6H4
4-ClC6H4
4-NH2SO2C6H4
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
Ph
14b
14c
14d
14e
14f
14g
14h
Ph
Ph
4-ClC6H4
4-MeOC6H4
Ph
Ph
Ph
4-MeOC6H4
Thiophen-2-yl
Pyridin-4-yl
Pyridin-4-yl
Pyridin-4-yl
4-ClC6H4
4-FC6H4
analysis for single crystal of 15b (Figure 3, Tables 2 and 3)19 showed the structure (1Z)-1-[2-
(aryl)hydrazinylidene]-2-oxopropyl (1Z)-N-(aryl)-2-oxopropanehydrazonothioates 15a–e
for these products and proved that the reaction proceeded in 2:1 molar ratio for 1a:2a–e.
Similarly, the above reaction was conducted for 1a with ethyl 2-chloro-2-(2-
phenylhydrazono)acetate 2f (R = COOEt, Ar2 = Ph) and N’-phenylbenzohydrazonoyl
chloride 2g (R = Ar2 = Ph), respectively, and the products were found to be hydra-
zonothioates 15f and 15g, respectively, in addition to 1,3,4-oxadiazole 14a, in each case.
The reaction of 1b–h with 2a gave, in each case, (1Z)-1-[2-(phenyl)hydrazinylidene]-2-
oxopropyl (1Z)-N-(phenyl)-2-oxopropanehydrazonothioate 15a in addition to the corre-
sponding 1,3,4-oxadiazoles 14b–h (Scheme 1, Table 1).
The possible mechanism for the cyclodesulfurization reaction of thiosemicarbazide
1 by 2 is shown in Figure 4. This reaction is proposed to proceed following pathway A via
a preliminary formation of intermediate thiohydrazonate 16. This conversion involves the
initial reaction of -SH tautomer 1A with nitrilimine 10 to form this desired intermediate,
which activates cyclization process to form 1,3,4-oxadiazole thiohydrazonate 17. The latter
Figure 3 ORTEP diagram of 15b, 50% probability ellipsoid.

1332
H. A. ABDEL-AZIZ ET AL.
Table 2 The crystallographic data and refinement information for 15b
Compound
15b
Empirical formula
Formula weight
C20H22N4O2S
382.48
Crystal system
Space group
Monoclinic
P21/c
a/Å
b/Å
c/Å
α/◦
β/◦
γ /◦
V/Å3
Z
11.785 (1) Å
8.0747 (7) Å
21.3142 (19) Å
90◦
103.818 (3)◦
90◦
1969.6 (3) Å3
4
0.19 mm−1
Yellow/crystal
294 K
μ (mm−1
)
Color/shape
Temp (K)
Rint
θmax
0.102
27.5◦
Goodness of fit on F2
Measured reflections
Independent reflections
R[F2 > 2σ(F2)]
wR(F2)
1.04
41731
4525
0.087
0.239
ꢀρmax
ꢀρmin
0.37 eÅ−3
−0.35 eÅ−3
intermediate undergoes in situ Smiles rearrangement20 as soon as they are formed to
yield the thiohydrazides 20. Then the consequent cyclization of intermediate 20 combined
with the elimination of thiol 22, which reacts with another molecule of 10, leads to the
formation of 14 and 15 as final products. The second possible pathway B involves 1,3-
dipolar cycloaddition reaction of 10 into C S tautomer 1B to give the spirointermediate
18 that undergoes in situ Smiles rearrangement to form thiohydrazides 19 and then the
cyclized intermediate 20. On the other side, the formation of carbodiimide 21 as nonisolable
Table 3 Characteristic bond lengths [Å] and angles [◦] of 15b
Bond lengths [Å]
Bond angles [◦]
S1–C3
1.781 (4)
1.789 (3)
1.222 (5)
1.227 (5)
1.323 (4)
1.295 (5)
1.414 (5)
1.313 (4)
1.301 (4)
1.412 (5)
C3–S1–C10
N2–N1–C3
N1–N2–C4
N4–N3–C10
N3–N4–C13
O1–C2–C1
O1–C2–C3
S1–C3–C2
N1–C3–C2
S1–C3–N1
102.03 (16)
120.5 (3)
118.4 (3)
120.0 (3)
119.9 (3)
121.2 (3)
120.2 (3)
118.7 (3)
116.2 (3)
125.1 (3)
S1–C10
O1–C2
O2–C11
N1–N2
N1–C3
N2–C4
N3–N4
N3–C10
N4–C13

CYCLODESULFURIZATION OF SUBSTITUTED THIOSEMICARBAZIDES
1333
2
B
B.HCl
[1A
1B + 10 ]
Pathway B
Pathway A
O
O
H
N
N
H
N
H
Ar
O
Ar
N
H
Ar1
N
SH
N
Ar1
H
N
H
N
N
S
Ar
N
H
Ar1
+
N
N
S
R
R
N
22
Ar2
H
N
Ar2
R
N
21
Ar2
18
16
10
Ar2
Ar
HN
R
N
N
N
N
O
Ar1
Ar
HN
O
Ar
N
H
S
N
O
R
Ar1
NH
N
N
H
H
14
S
HN
15
N
H
Ar2
Ar1
N
SH
R
Ar2
N
N
17
R
N
Ar2
19
Ar
N
HN
SH
O
Ar1
14
+
22
N
H
N
10
15
R
N
Ar2
20
Figure 4 Mechanism for the reaction of thiosemicarbazides 1a–h with hydrazonoyl chlorides 2a–g.
intermediate and its subsequent cyclization resulting in 1,3,4-oxadiazoles 14 is possible
third pathway.17
CONCLUSION
In conclusion, isolation of unexpected cyclodesulfurization products, 1,3,4-
oxadiazoles 14a–h, with moderate yields, from the reaction of 1a–h with 2a–g, showed the
significant behavior of hydrazonoyl chlorides 2a–g toward 1a–h rather than their ordinary
behaviors with possible products.
EXPERIMENTAL
General
Infrared (IR) spectra were recorded as KBr disks using a Perkin Elmer FT-IR Spec-
trum BX apparatus. Melting points were determined on a Gallenkamp melting point ap-
paratus and are uncorrected. NMR spectra were scanned in DMSO-d6 on a Bruker NMR
spectrometer operating at 500 MHz for 1H and 125.76 MHz for 13C at the Research Center,
College of Pharmacy, King Saud University, Saudi Arabia. Chemical shifts are expressed

1334
H. A. ABDEL-AZIZ ET AL.
in δ values (ppm) relative to tetramethylsilane (TMS) as an internal standard. Coupling
constants (J) are expressed in Hz and D2O was added to confirm the exchangeable protons.
Mass spectra were measured on an Agilent Triple Quadrupole 6410 QQQ LC/MS equipped
with an ESI (electrospray ionization) source. The elemental analyses were performed at
the Microanalytical Center of Cairo University. The homogeneity of the compounds was
checked by TLC performed on Silica gel G coated plates (Merck). An iodine chamber was
used for the visualization of TLC spots.
N-(4-Aryl)-2-aryl1-carbonyl)hydrazinecarbothioamides 1a–h5,17,21 and hydrazonoyl
chlorides 2a–g22–24 were prepared according to the reported method.
The Reaction of Thiosemicarbazides 1 with Hydrazonoyl Chlorides 2
To a solution of compounds 1a–h (10 mmol) in absolute ethanol (50 mL), the
appropriate hydrazonoyl chloride 2a–g (20 mmol) and triethylamine (40 mmol) were
added. The reaction mixture was stirred overnight. The solvent was evaporated, and then
the remained residue was treated with water (20 mL). The solid formed was collected
by filtration and washed with water. The fractional recrystallization of the solid formed
from n-hexane afforded the insoluble compounds 14a–h and the soluble hydrazonothioates
15a–g.
The physical properties and spectroscopic data of 1,3,4-oxadiazoles 14a–f,5,17 hy-
drazonothioates 15f,25 and 15g8 were found to be identical with those described in the
literature.
N-(4-Chlorophenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine (14g)
◦
Colorless powder; mp: 310–312 C (ethanol (EtOH)/dimethylformamide (DMF))
(Lit. mp = 238–240 ◦C).26
N-(4-Fluorophenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine (14h)
Colorless crystals; mp: 250–252 ◦C (EtOH/DMF); IR (KBr) v 3279 (NH) cm−1, 1H
NMR (500 MHz, DMSO-d6) δ: 7.61–8.80 (m, 8H, Ar-H), 10.85 (s, D2O exch., 1H, NH);
13C NMR (125 MHz, DMSO-d6) δ: 117.2, 118.4, 119.8, 120.8, 134.0, 144.3, 150.7, 153.3,
156.0 (C N), 164.2 (C N), 166.3 (C N); MS (ESI) m/z: 257.1 [M+1]+. Anal. Calcd. for
C13H9FN4O (256.24): C, 60.94; H, 3.54; N, 21.87%. Found: C, 59.82; H, 3.65; N, 22.02%.
(1Z)-2-Oxo-1-(2-phenylhydrazinylidene)propyl-(1Z)-2-oxo-N-phenylpropaneh-
ydrazonothioate (15a)
◦
Pale yellow fibers; mp: 215–217 C (EtOH/DMF); IR (KBr) v 3178 (NH), 1648
(C O), 1531 (C N) cm−1; H NMR (500 MHz, DMSO-d6) δ: 2.29 (s, 6H, 2CH3),
1
7.10–7.42 (m, 6 H, Ar-H), 7.47–7.91 (m, 4 H, Ar-H), 11.01 (s, D2O exch., 2H, 2NH);
13C NMR (125 MHz, DMSO-d6) δ: 24.9 (CH3), 116.1, 120.1, 126.0, 127.4, 128.4, 129.0,
133.8, 141.3, 146.9 (C N), 194.1 (C O); MS (ESI) m/z: 355.2 [M+1]+; Anal. Calcd. for
C18H18N4O2S (354.43): C, 61.00; H, 5.12; N, 15.81; S, 9.05%. Found: C, 61.23; H, 5.04;
N, 15.96; S, 9.07%.

CYCLODESULFURIZATION OF SUBSTITUTED THIOSEMICARBAZIDES
1335
(1Z)-1-[2-(2-Methylphenyl)hydrazinylidene]-2-oxopropyl-(1Z)-N-(2-methylph-
enyl)-2-oxopropanehydrazonothioate (15b)
Yellow crystals; mp: 220–222 ◦C (EtOH/DMF); IR (KBr) v 3165 (NH), 1658 (C O),
1540 (C N) cm−1; 1H NMR (500 MHz, DMSO-d6) δ: 2.22 (s, 6H, 2CH3), 2.30 (s, 6H,
2CH3), 6.61–6.96 (m, 5H, Ar-H), 7.05–7.33 (m, 3H, Ar-H), 11.23 (s, D2O exch., 2H, 2NH);
13C NMR (125 MHz, DMSO-d6) δ: 16.7 (CH3), 25.0 (CH3), 115.7, 124.1, 127.9, 128.4,
129.2, 140.3, 146.7 (C N), 194.5 (C O); MS (ESI) m/z: 382.7 [M]+; Anal. Calcd. for
C20H22N4O2S (382.48): C, 62.80; H, 5.80; N, 14.65; S, 8.38%. Found: C, 62.55; H, 5.78;
N, 14.77; S, 8.46%.
(1Z)-1-[2-(4-Bromophenyl)hydrazinylidene]-2-oxopropyl-(1Z)-N-(4-bromoph-
enyl)-2-oxopropanehydrazonothioate (15c)
Yellow fibers; mp: 210–212 ◦C (EtOH/DMF); IR (KBr) v 3190 (NH), 1644 (C O),
1527 (C N) cm−1; 1H NMR (500 MHz, DMSO-d6) δ: 2.35 (s, 6H, 2CH3), 7.11–7.25 (m,
4H, Ar-H), 7.31–7.65 (m, 4H, Ar-H), 11.10 (s, D2O exch., 2H, 2NH); 13C NMR (125 MHz,
DMSO-d6) δ: 25.1 (CH3), 114.8, 123.4, 128.8, 129.5, 144.8 (C N), 194.0 (C O); MS
(ESI) m/z: 515.2 [M+3]+; Anal. Calcd. for C18H16N4O2SBr (512.22): C, 42.21; H, 3.15;
N, 10.94; S, 6.26%. Found: C, 42.37; H, 3.14; N, 11.08; S, 6.14%.
(1Z)-1-[2-(4-Chlorophenyl)hydrazinylidene]-2-oxopropyl-(1Z)-N-(4-chloroph-
enyl)-2-oxopropanehydrazonothioate (15d)
Yellow needles; mp: 290–292 ◦C; IR (KBr) v 3208 (NH), 1653 (C O), 1536 (C N)
1
cm−1; H NMR (500 MHz, DMSO-d6) δ: 2.31 (s, 6H, 2CH3), 7.05–7.37 (m, 4H, Ar-H),
7.48–8.02 (m, 4H, Ar-H), 11.10 (s, D2O exch., 2H, 2NH); 13C NMR (125 MHz, DMSO-d6)
δ: 25.3 (CH3), 114.5, 125.4, 126.4, 127.3, 131.2, 137.8, 145.1 (C N), 192.8 (C O); MS
(ESI) m/z: 424.3 [M+1]+; Anal. Calcd. for C18H16N4O2SCl (423.32): C, 51.07; H, 3.81;
N, 13.24; S, 7.57%. Found: C, 50.94; H, 3.89; N, 13.20; S, 7.65%.
(1Z)-1-[2-(4-Sulphonamidophenyl)hydrazinylidene]-2-oxopropyl-(1Z)-N-
(4-sulphoamidophenyl)-2-oxopropanehydrazonothioate (15e)
Yellow crystals; mp: 258–260 ◦C; IR (KBr) v 3400–3000 (NH+NH2), 1651 (C O),
1533 (C N) cm−1; 1H NMR (500 MHz, DMSO-d6) δ: 2.30 (s, 6H, 2CH3), 7.5 (d, 4H, J
= 8.5 Hz, Ar-H), 7.35 (s, D2O exch., 2H, SO2NH2), 7.70 (d, 4H, J = 8.5 Hz, Ar-H), 11.09
(s, D2O exch., 2H, 2NH); 13C NMR (125 MHz, DMSO-d6) δ: 25.0 (CH3), 115.9, 128.7,
128.9, 130.8, 131.1, 144.9 (C N), 194.3 (C O); MS (ESI) m/z: 512.6 [M]+; Anal. Calcd.
for C18H20N4O6S3 (512.58): C, 42.18; H, 3.93; N, 16.40; S, 18.77%. Found: C, 42.02; H,
3.99; N, 16.56; S, 18.92%.
FUNDING
The authors extend their appreciation to the Deanship of Scientific Research at King
Saud University for funding this work through research group no. RGP-VPP-321.

1336
H. A. ABDEL-AZIZ ET AL.
SUPPLEMENTAL MATERIAL
Supplemental data for this article can be accessed on the publisher’s website,
www.tandfonline.com/gpss
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