Synthesis of 1,2,4,5-tetrakis(1,2,4-triazolyl) benzene and 1,2,4,5-tetrakis(1,3,4-oxadiazolyl) benzene derivatives

Article abstract of DOI:10.1080/10426507.2011.597801

A series of 1,2,4,5-tetrakis(1,2,4-triazolyl)benzenes and 1,2,4,5-tetrakis(1,3,4-oxadiazolyl)benzenes was synthesized by nucleophilic addition of sodium salts of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 1,3,4-oxadiazole-2(3H)-thiones to 1,2,4,5-tetrakis(bromomethyl)benzene. The structure of the newly synthesized compounds was confirmed by elemental analysis, IR and ¹H and ¹³C NMR spectra. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: 1H and 13C NMR spectra of products (Figures S1-S24).

Full text of DOI:10.1080/10426507.2011.597801

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Synthesis of 1,2,4,5-Tetrakis(1,2,4-
Triazolyl) Benzene and 1,2,4,5-
Tetrakis(1,3,4-Oxadiazolyl) Benzene
Derivatives
Abbas Nikoo a & Karim Akbari Dilmaghani a
a Department of Chemistry, Faculty of Science, Urmia University,
Urmia, Iran
Available online: 05 Jan 2012
To cite this article: Abbas Nikoo & Karim Akbari Dilmaghani (2012): Synthesis of 1,2,4,5-
Tetrakis(1,2,4-Triazolyl) Benzene and 1,2,4,5-Tetrakis(1,3,4-Oxadiazolyl) Benzene Derivatives,
Phosphorus, Sulfur, and Silicon and the Related Elements, 187:2, 268-275
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Phosphorus, Sulfur, and Silicon, 187:268–275, 2012
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2011.597801
SYNTHESIS OF 1,2,4,5-TETRAKIS(1,2,4-TRIAZOLYL)
BENZENE AND 1,2,4,5-TETRAKIS(1,3,4-OXADIAZOLYL)
BENZENE DERIVATIVES
Abbas Nikoo and Karim Akbari Dilmaghani
Department of Chemistry, Faculty of Science, Urmia University, Urmia, Iran
GRAPHICAL ABSTRACT
N
N
R
R
N
S
N
S
X
X
X
Br
Br
Br
Br
H
N
NaOH / DMF
80 oC
N
S
+
X
R
S
N
S
N
X
X = O , NPh
R
R
N
N
Abstract A series of 1,2,4,5-tetrakis(1,2,4-triazolyl)benzenes and 1,2,4,5-tetrakis(1,3,4-
oxadiazolyl)benzenes was synthesized by nucleophilic addition of sodium salts of
4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and 1,3,4-oxadiazole-2(3H)-thiones to
1,2,4,5-tetrakis(bromomethyl)benzene. The structure of the newly synthesized compounds was
confirmed by elemental analysis, IR and 1H and 13C NMR spectra.
Supplemental materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental
resource: 1H and 13C NMR spectra of products (Figures S1-S24).
Keywords 1,3,4-Oxadiazole; 1,2,4,5-tetrakis(bromomethyl)benzene; 1,2,4-triazole
INTRODUCTION
Heterocycles containing sulfur atoms represent an important group of sulfur com-
pounds that are promising for use in practical applications. Moreover, these heterocycles are
of great utility in preparative organic chemistry. Among these, the mercapto-1,2,4-triazoles
and mercapto-1,3,4-oxadiazoles have been well studied and a large number of derivatives
have been used. It was reported that by alkylation of 1,2,4-triazolethiones and 1,3,4-
oxadiazolethiones with alkyl halides in an alkali solution, S-alkylated derivatives could
Received 8 March 2011; accepted 9 June 2011.
The authors gratefully acknowledge the financial support at this work by the Research Council of Urmia
University.
Address correspondence to Karim Akbari Dilmaghani, Department of Chemistry, Faculty of Science, Urmia
University, 57159 Urmia, Iran. E-mail: kadilmaghani@yahoo.com
268

SYNTHESIS OF 1,2,4,5-TETRAKIS(1,2,4-TRIAZOLYL)BENZENE
269
be prepared successfully.1–3 In this context, the biological activity of S-alkylated of 1,2,4-
triazolethiones and 1,3,4-oxadiazolethiones is well known and it was found out that the bac-
teriostatic and diuretic activity of S-alkylated-1,2,4-triazolethiones correlates with the size
of the alkyl groups.4 Several S-alkylated-1,2,4-triazolethiones were synthesized with anti-
inflammatory,5,6 antibacterial, and antifungal activities.7 The S-alkylated-1,3,4-oxadiazoles
showed in vitro activity against Mycobacterium tuberculosis.8 The antihepatitis-B virus
activity,10 bactericidal,11 antifungal,12,13 genotoxic activity,14 antituberculosis,15 antimi-
crobial, and anti-HIV-1 activity9 have been also reported for 2-substituted thio-1,3,4-
oxadiazoles.
Therefore, in the light of these interesting biological activities, we decided
to synthesize some new 1,2,4,5-Tetrakis(1,2,4-triazolyl)benzenes 4a–g and 1,2,4,5-
Tetrakis(1,3,4-oxadiazolyl) benzenes 6c–g by nucleophilic substitution of 1,2,4,5-
tetrakis(bromomethyl)benzene with the corresponding 4-phenyl-2,4-dihydro-3H-1,2,4-
triazole-3-thiones 3a–g and 1,3,4-oxadiazole-2(3H)-thiones 5c–g in an alkali solution of
dimethylformamide (DMF) at 80 ◦C (Schemes 1 and 2).
H
O
N
N
H
N
H
N
S
1) NaOH 2N / reflux
2) HCl
R
N
H
N
R
S
2(a-g)
PhNCS
EtOH
reflux
3(a-g)
Br
Br
Br
NaOH
DMF
80 oC
O
NH2
R
N
H
Br
1(a-g)
N
N
R
R
N
N
Me
N
N
N
N
Me
a
R :
S
S
Me
OH
c
b
d
S
S
N
Cl
N
O
N
R
R
N
N
e
g
f
4(a-g)
Scheme 1

270
A. NIKOO AND K. A. DILMAGHANI
N
N
R
R
N
S
N
O
O
O
O
S
H
O
NaOH / DMF / 80 oC
N
1) CS2 / KOH / EtOH / reflux
2) HCl
N
S
NH2
R
N
H
O
Br
Br
R
S
N
S
N
1(c-g)
5(c-g)
R
R
N
N
Br
O
Br
6(c-g)
Cl
N
R :
OH
c
d
e
f
g
Scheme 2
RESULTS AND DISCUSSION
The synthesis of 1,2,4,5-tetrakis(1,2,4-triazolyl)benzenes 4a–g is outlined in Scheme
1. Reaction of carboxylic acid hydrazides 1a–g with phenylisothiocyanate in ethanol
gave 1-substituted-4-phenylthiosemicarbazides 2a–g. Cyclization of compounds 2a–g was
accomplished in an aqueous alkaline media to give 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-
3-thiones 3a–g according to the literature.16 In addition, it was reported that the crys-
talline form of 1,2,4-triazolethiones existed as the thione tautomer. They showed, however,
thiol-thione tautomerism in solution.17,18 The reaction of 4-phenyl-2,4-dihydro-3H-1,2,4-
triazole-3-thiones 3a–g with 1,2,4,5-tetrakis(bromomethyl)benzene in the presence of
NaOH in DMF gave 1,2,4,5-tetrakis(1,2,4-triazolyl)benzenes 4a–g. The IR spectra of com-
pounds 4a–g clearly showed the stretching vibration band between at 1590 and 1600 cm−1
1
which was attributed to the C N double bond of 1,2,4-triazole. In the H NMR spectra,
the protons signals due to methylene groups (ArCH2S) were recorded between at 4.03 and
4.56 ppm with integrals of eight protons. The 13C signals of these groups (ArCH2S) ap-
peared between at 33.75 and 34.30 ppm. In the 13C NMR spectra of compounds 4a–g, two
signals belong to the N C N group of 1,2,4-triazole which appeared between at 145.55
and 160.82 ppm.
The synthetic pathway leading to 1,2,4,5-tetrakis(1,3,4-oxadiazolyl)benzenes 6c–g is
shown in Scheme 2. 1,3,4-Oxadiazole-2(3H)-thiones 5c–g were synthesized by the reaction
of carboxylic acid hydrazides 1c–g with carbon disulfide in the presence of potassium
hydroxide followed by a condensation reaction according to the literature.19 In 1956,
Ainsworth found that 1,3,4-oxadiazolethiones exist in the thione form.20 Later studies by
spectroscopic methods gave the same result.21 The reaction of 1,3,4-oxadiazole-2(3H)-
thiones 5c–g with 1,2,4,5-tetrakis(bromomethyl)benzene under the same condition as 4a–g
gave 1,2,4,5-tetrakis(1,3,4-oxadiazolyl)benzenes 6c–g. In the IR spectra of compounds
6c–g, the observed absorption band at 1588–1670 cm−1 is duo to C N of 1,3,4-oxadiazole.
1
The H NMR spectra of compounds 6c–g shows a multiplet at 4.63–4.69 ppm with an
integral of eight protons of the methylene groups (ArCH2S). The peak belonging to the
same groups was observed between at 33.41 and 33.54 ppm in the 13C NMR spectra. In
1
the H NMR spectra of compounds 6c–g, the signal observed at 7.63–7.74 ppm with an

SYNTHESIS OF 1,2,4,5-TETRAKIS(1,2,4-TRIAZOLYL)BENZENE
271
integral of two protons was assigned to ArH of benzene ring. The 13C NMR spectra of
1,3,4-oxadiazole shows two signals belonging to O C N between 145.55 and 160.82
ppm.
CONCLUSION
In this study, we describe the synthesis of some new S-alkylated tetrakis-1,2,4-
triazoles and tetrakis-1,3,4-oxadiazoles by a nucleophilic substitution of 1,2,4,5-
tetrakis(bromomethyl)benzene with 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones and
1,3,4-oxadiazole-2(3H)-thiones. Characterization and check for purity of all compounds
were carried out by elemental analysis, IR, 1H, and 13C NMR spectroscopy.
EXPERIMENTAL
Melting points were determined on a Buchi 530 instrument and are uncorrected. IR
spectra were recorded by use of the FT-IR Thermo Nicolet Nexus 670 spectrometer (cm−1
,
KBr pellets). 1H NMR (300 MHz) 13C NMR (75 MHz) spectra were measured on a Bruker
300 MHz Ultra shield spectrometer using CDCl3 and DMSO-d6 as solvents. Elemental
analyses (C, H, N, and S) were performed on a Leco CHNS 932 analyzer.
Preparation of 1-Substituted-4-Phenylthiosemicarbazides
2a–g. General Procedure
A mixture of compounds 1a–g (0.01 mol) and phenylisothiocyanate (2 g, 0.015 mol)
was stirred in refluxing ethanol (100 mL) for 4 h to give a white precipitate. The mixture
was cooled to room temperature. The crude solid was then filtered and crystallized from
ethanol to yield the compounds 2(a–g).
Preparation of 4-Phenyl-2,4-Dihydro-3H-1,2,4-Triazole-3-Thiones 3(a–g).
General Procedure
An aqueous solution of NaOH (2N, 50 mL) and compounds 2a–g (0.01 mol) was
stirred under reflux conditions for 6h. After completion of the reaction, the mixture was
filtered and the filtrate was neutralized with conc. HCl up to pH 7. The mixture was kept
aside for few minutes to precipitate. The precipitated solid was filtered and washed with
water. Crystallization from ethanol afforded the compounds 3a–g.
Preparation of 1,3,4-Oxadiazole-2(3H)-Thiones 5(c–g).
General Procedure
Compounds 1c–g (0.01 mol) was dissolved in a hot solution of KOH (0.56 g, 0.01 mol)
in 96% ethanol (50 mL). CS2 (0.96 mL, 0.015 mol) was then added and the reaction mixture
was heated under reflux conditions for 6 h until the evolution of H2S ceased. The reaction
mixture was cooled to room temperature and diluted with water. Acidifying the mixture
with conc. HCl gave an oxadiazole precipitate. The solid was filtered, dried and crystallized
from ethanol to afford the compounds 5c–g.

272
A. NIKOO AND K. A. DILMAGHANI
Synthesis of 1,2,4,5-Tetrakis(1,2,4-Triazolyl)Benzenes 4a–g and
1,2,4,5-Tetrakis(1,3,4-Oxadiazolyl)Benzenes 6c–g. General Procedure
To a solution of 4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thiones 3a–g or 1,3,4-
oxadiazole-2(3H)-thiones 5c–g (1 mmol) in DMF (20 mL), NaOH (1 mmol, 40 mg) was
added and the mixture was stirred for 30 min at room temperature. After consumption
of NaOH 1,2,4,5-tetrakis(bromomethyl), benzene (0.2 mmol, 0.09 g) was added and the
mixture was heated at 75 ◦C–80 ◦C for 8–12 h. The mixture was then cooled to the room
temperature and distilled water (100 mL) was added to the resulting mixture. The pre-
cipitate was filtered and recrystallized in an appropriate solvent to give 1,2,4,5-tetrakis
(1,2,4-triazolyl)benzenes 4a–g or 1,2,4,5-tetrakis(1,3,4-oxadiazolyl)benzenes 6c–g. Sam-
ple spectra are presented in the Supplemental Materials (Figures S1–S24).
1,2,4,5-Tetrakis(5-Methyl-4-Phenyl-1,2,4-Triazol-3-yl-Thiomethyl)
Benzene (4a)
Yield: 70%, crystallized from EtOH, mp 208.5 ◦C–210.5 ◦C; IR: 3047, 3008, 2971,
1
2933, 1597, 1535, 1500, 1428, 772, 725, 694, 556; H NMR (CDCl3) δ: 2.21 (12H, s,
CH3), 4.22 (8H, s, ArCH2S), 6.98 (2H, s, ArH), 7.08 (8H, bs, ArH), 7.43 (12H, bs, ArH);
13C NMR (CDCl3) δ: 11.28, 34.17, 126.96, 129.88, 133.11, 135.16, 150.14, 152.92; Anal.
Calcd. for C46H42N12S4: 62.00 C, 4.75 H, 18.86 N, 14.39 S. Found: 62.08 C, 4.81 H, 18.82
N, 14.29 S.
1,2,4,5-Tetrakis(5-Isopropyl-4-Phenyl-1,2,4-Triazol-3-yl-Thiomethyl)
Benzene (4b)
Yield: 60%, crystallized from EtOH, mp 216 ◦C–218 ◦C; IR: 3054, 2970, 2930, 2871,
1596, 1518, 1497, 1439, 773, 700, 611; 1H NMR (CDCl3) δ: 1.19 (24H, d, J = 6.9Hz, CH3),
2.75 (4H, sep, J = 6.9Hz, CH), 4.18 (8H, s, ArCH2S), 7.00 (10H, bs, ArH), 7.41–7.44
(12H, m, ArH); 13C NMR (CDCl3) δ: 21.01, 25.42, 34.12, 127.37, 129.81, 129.90, 133.17,
133.27, 135.28, 150.03, 160.82; Anal. Calcd. for C54H58N12S4: 64.64 C, 5.83 H, 16.75 N,
12.78 S, Found: 64.71 C, 5.89 H, 16.68 N, 12.72 S.
1,2,4,5-Tetrakis(5-Phenyl-4-Phenyl-1,2,4-Triazol-3-yl-Thiomethyl)
Benzene (4c)
Yield: 58%, crystallized from EtOH/DMF, mp 262.5 ◦C–264.5 ◦C; IR: 3062, 2936,
1
2912, 1594, 1497, 1473, 1447, 1424, 1380, 771, 694, 601; H NMR (CDCl3) δ: 4.56
(8H, S, ArCH2S), 7.23–7.45 (42H, m, ArH); 13C NMR (CDCl3) δ: 33.94, 125.42, 127.40,
128.44, 128.53, 130.05, 130.18, 133.53, 133.68, 135.20, 152.53, 154.62; Anal. Calcd.
for C66H50N12S4: 69.57 C, 4.42 H, 14.75 N, 11.26 S. Found: 69.67 C, 4.53 H, 14.64 N,
11.16 S.
1,2,4,5-Tetrakis[5-(4-Hydroxyphenyl)-4-Phenyl-1,2,4-Triazol-3-
yl-Thiomethyl]Benzene (4d)
◦
◦
Yield: 55%, crystallized from EtOH, mp 225 C–227 C. IR: 3405, 3238, 3189,
1
3051, 2855, 1600, 1558, 1496, 1454, 1235, 749, 693; H NMR (DMSO-d6) δ: 4.03 (8H,
s, ArCH2S), 6.82 (4H, t, J = 6.9 Hz, ArH), 6.91 (2H, s, ArH), 7.17 (15H, s, ArH), 7.41
(17H, m, ArH), 8.30 (4H, s, ArOH); 13C NMR (DMSO-d6) δ: 34.30, 117.50, 121.00,
128.21, 129.02, 130.11, 132.55, 132.90, 135.35, 141.73, 145.55, 152.63; Anal. Calcd. for

SYNTHESIS OF 1,2,4,5-TETRAKIS(1,2,4-TRIAZOLYL)BENZENE
273
C66H50N12O4S4: 65.87 C, 4.19 H, 13.96 N, 10.66 S. Found: 65.94 C, 4.23 H, 13.91 N,
10.59 S.
1,2,4,5-Tetrakis[5-(2-Chlorophenyl)-4-Phenyl-1,2,4-
Triazol-3-yl-Thiomethyl]Benzene (4e)
Yield: 50%, crystallized from EtOH, mp 160 ◦C–162 ◦C. IR : 3052, 2969, 2872, 1596,
1530, 1496, 1422, 1383, 765, 728, 695, 605; 1H NMR (CDCl3) δ: 4.54 (8H, s, ArCH2S),
5.30 (2H, s, ArH), 7.01 (8H, d, J = 7.5 Hz, ArH), 7.21–7.31 (24H, m, ArH), 7.50 (4H, d,
J = 7.2 Hz, ArH); 13C NMR (CDCl3) δ: 34.09, 126.28, 126.74, 126.79, 129.41, 129.56,
129.65, 131.62, 132.75, 132.98, 133.74, 134.23, 135.26, 151.52, 153.41; Anal. Calcd. for
C66H46Cl4N12S4: 62.07 C, 3.63 H, 13.16, 10.04 N. Found: 62.16 C, 3.58 H, 13.07 N,
10.11 S.
1,2,4,5-Tetrakis[5-(2-Pyridyl)-4-Phenyl-1,2,4-Triazol-3-
yl-Thiomethyl]Benzene (4f)
Yield: 63%, crystallized from EtOH/DMF, mp 156 ◦C–158 ◦C. IR: 3053, 3005, 2968,
2940, 1590, 1568, 1499, 1453, 1447, 1417, 1381, 788, 693, 596; 1H NMR (CDCl3) δ: 4.50
(8H, S, ArCH2S), 7.14–7.19 (13H, m, ArH), 7.32–7.38 (13H, m, ArH), 7.69 (4H, t, J =
7.8 Hz, PyH), 8.04 (4H, d, J = 7.8 Hz, PyH), 8.25 (4H, d, J = 3.9 Hz, PyH); 13C NMR
(CDCl3) δ: 33.75, 123.68, 123.89, 127.29, 129.18, 129.27, 133.56, 134.71, 135.23, 136.58,
146.46, 148.87, 153.34, 153.82; Anal. Calcd. for C62H46N16S4: 65.13 C, 4.05 H, 19.60 N,
11.22 S. Found: 65.21 C, 4.11 H, 19.53 N, 11.15 S.
1,2,4,5-Tetrakis[5-(2-Furyl)-4-Phenyl-1,2,4-Triazol-3-yl-Thiomethyl]
Benzene (4g)
Yield: 66%, crystallized from EtOH/DMF, mp 255 ◦C–257 ◦C. IR: 3148, 3112, 3062,
3013, 2944, 1619, 1595, 1513, 1498, 1445, 1423, 1402, 1371, 1254, 1226, 1017, 1008,
1
902, 752, 696, 619, 594; H NMR (CDCl3) δ: 4.41 (8H, s, ArCH2S), 6.14 (4H, s, furyl),
6.28 (4H, s, furyl), 7.19–7.47 (26H, m, ArH); 13C NMR (CDCl3) δ: 33.99, 111.19, 111.49,
127.50, 129.84, 130.25, 133.43, 135.22, 141.29, 143.94, 147.86, 151.65; Anal. Calcd. for
C58H42N12O4S4: 63.37 C, 3.85 H, 15.29 N, 11.67 S. Found: 63.42 C, 3.94 H, 15.18 N,
11.58 S.
1,2,4,5-Tetrakis(5-Phenyl-1,3,4-Oxadiazol-2-yl-Thiomethyl)Benzene (6c)
◦
◦
Yield: 73%, crystallized from MeOH/CHCl3, mp 162 C–164 C; IR: 3059, 2927,
1
1610, 1555, 1470, 1189, 1066, 773, 698; H NMR (CDCl3) δ: 4.68 (8H, S, ArCH2S),
7.46 (12H, bs, ArH), 7.72 (2H, s, ArH), 7.77–7.92 (8H, bs, ArH); 13C NMR (CDCl3) δ:
33.49, 123.41, 126.68, 129.01, 131.71, 133.82, 135.06, 163.13, 166.02; Anal. Calcd. for
C42H30N8O4S4: 60.13 C, 3.60 H, 13.36 N, 15.29 S. Found: 60.18 C, 3.62 H, 13.31 N,
15.21 S.
1,2,4,5-Tetrakis[5-(4-Hydroxyphenyl)-1,3,4-Oxadiazol-2-yl-
Thiomethyl]Benzene (6d)
Yield: 69%, crystallized from EtOH, mp 237 ◦C–239 ◦C. IR: 3153, 2945, 2814, 1609,
1494, 1475, 1441, 1280, 1237, 1193, 1169, 1071, 839; 1H NMR (DMSO-d6) δ: 4.63 (8H,
s, ArCH2S), 6.87 (8H, d, J = 8.1 Hz, ArH), 7.63 (2H, s, ArH), 7.68 (8H, d, J = 8.1 Hz,
ArH), 10.25 (4H, s, ArOH); 13C NMR (DMSO-d6) δ: 33.54, 114.2, 116.51, 128.82, 133.37,

274
A. NIKOO AND K. A. DILMAGHANI
135.54, 161.21, 162, 165.98; Anal. Calcd. for C42H30N8O8S4: 55.86 C, 3.35 H, 12.41 N,
14.20 S. Found: 55.93 C, 3.37 H, 12.39 N, 14.13 S.
1,2,4,5-Tetrakis[5-(2-Chlorophenyl)-1,3,4-Oxadiazol-2-yl-Thiomethyl]
Benzene (6e)
◦
◦
Yield: 66%, crystallized from MeOH/CHCl3, mp 141 C–143 C. IR: 3068, 2993,
2926, 1670, 1596, 1573, 1469, 1189, 1090, 1034, 764, 727; 1H NMR (CDCl3) δ: 4.68 (8H,
s, ArCH2S), 7.31–7.44 (12H, m, ArH), 7.71 (2H, s, ArH), 7.85 (4H, d, J = 5.7 Hz, ArH); 13
C
NMR (CDCl3) δ: 33.50, 122.64, 127.05, 130.89, 131.19, 132.37, 132.91, 133.76, 135.03,
163.75, 164.26; Anal. Calcd. for C42H26Cl4N8O4S4: 51.64 C, 2.68 H, 11.47 N, 13.13 S.
Found: 54.74 C, 2.74 H, 11.41 N, 13.07 S.
1,2,4,5-Tetrakis[5-(2-Pyridyl)-1,3,4-Oxadiazol-2-yl-Thiomethyl]
Benzene (6f)
◦
◦
Yield: 79%, crystallized from MeOH/CHCl3, mp 216 C–218 C. IR: 3055, 2995,
1
2926, 1588, 1554, 1462, 1197, 1086, 793, 740, 707; H NMR (CDCl3) δ: 4.69 (8H, S,
ArCH2S), 7.40 (4H, t, J = 6.9 Hz, PyH), 7.74 (2H, s, ArH), 7.82 (4H, t, J = 7.5 Hz, PyH),
8.13 (4H, d, J = 7.8 Hz, PyH), 8.71 (4H, d, J = 4.2 Hz, PyH); 13C NMR (CDCl3) δ: 33.41,
122.88, 125.75, 134.09, 134.97, 137.22, 143.10, 150.17, 164.72, 165.01; Anal. Calcd. for
C38H26N12O4S4: 54.14 C, 3.11 H, 19.94 N, 15.22 S. Found: 54.25 C, 3.14 H, 19.87 N,
15.15 S.
1,2,4,5-Tetrakis[5-(2-Furyl)-1,3,4-Oxadiazol-2-yl-Thiomethyl]
Benzene (6g)
◦
◦
Yield: 70%, crystallized from MeOH/CHCl3, mp 111 C–113 C. IR: 3125, 2929,
1630, 1529, 1471, 1156, 1090, 753; 1H NMR (CDCl3) δ: 4.63 (8H, s, ArCH2S), 6.55 (4H,
s, furyl), 7.08 (4H, s, furyl), 7.59 (4H, s, furyl), 7.66 (2H, s, ArH); 13C NMR (CDCl3) δ:
33.50, 112.15, 114.13, 133.86, 134.95, 138.90, 145.75, 158.75, 162.58; Anal. Calcd. for
C34H22N8O8S4: 51.12 C, 2.78 H, 14.03 N, 16.06 S. Found: 51.19 C, 2.83 H, 13.98 N, 16.01
S.
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