Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles

Article abstract of DOI:10.1134/S1070428020060172

Abstract: A series of novel 5-(1,2,3-triazolylmethylsulfanyl)tetrazole derivatives were synthesized by the click reaction from 1-phenyl-5-(prop-2-yn-1-ylsulfanyl)-1H-tetrazole and the corresponding azide. The reaction optimization results showed that higher yields are obtained using CuSO₄ and sodium ascorbate in DMF–water (2:1). The product structures were established on the basis of various spectral data, and their evaluation for antimicrobial activity showed moderate to good results compared to standard drugs.

Full text of DOI:10.1134/S1070428020060172

ISSN 1070-4280, Russian Journal of Organic Chemistry, 2020, Vol. 56, No. 6, pp. 1077–1081. © Pleiades Publishing, Ltd., 2020.
Synthesis of 5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-
1-phenyl-1H-tetrazoles
K. Thotlaa, V. G. Noolea, B. Kedikaa, and C. H. Krishna Reddya,*
a Department of Chemistry, Osmania University, Hyderabad, 500007 India
*e-mail: chkrishnarreddy@gmail.com
Received January 7, 2020; revised March 12, 2020; accepted March 15, 2020
Abstract—A series of novel 5-(1,2,3-triazolylmethylsulfanyl)tetrazole derivatives were synthesized by the
click reaction from 1-phenyl-5-(prop-2-yn-1-ylsulfanyl)-1H-tetrazole and the corresponding azide. The reaction
optimization results showed that higher yields are obtained using CuSO4 and sodium ascorbate in DMF–water
(2:1). The product structures were established on the basis of various spectral data, and their evaluation for
antimicrobial activity showed moderate to good results compared to standard drugs.
Keywords: tetrazole, 1,2,3-triazole, antimicrobial activity, click reaction
DOI: 10.1134/S1070428020060172
INTRODUCTION
found in active pharmaceutical ingredients such as
Cefamandole, Latamoxef, and Azosemide [20–22]
(Fig. 1). 1,2,3-Triazoles also demonstrate a wide
variety of pharmacological activities such as antimicro-
bial, antibacterial [23], fungicidal [24], antiallergic
[25], anti-HIV [26], anticancer [27], antioxidant [28],
etc. In view of the biological importance of tetrazole
and 1,2,3-triazole derivatives and in continuation of
our research work [29, 30], we made an attempt to
combine these two important pharmacophores in
a single molecule through a sulfur linkage (Scheme 1).
1,2,3-Triazoles and tetrazoles have provided a sig-
nificant contribution to medicinal chemistry. Tetrazole
derivatives are applicable in pharmaceutics, material
science, photography, and information recording sys-
tems and are attractive as ligands in coordination
chemistry [1–5]. Tetrazole derivatives possess various
biological activities, including antibacterial [6], anti-
fungal [7], antiviral [8], analgesic [9] and anti-inflam-
matory activities [10]. In addition, sulfanyl-substituted
hetaryl compounds are present in many natural prod-
ucts, drugs, [11] enzymes, and structural cell proteins
[12]. Drug molecules having sulfur atom in their core
structure are employed to treat Alzheimer’s and
Parkinson’s diseases, cancer, malaria, inflammations,
and AIDS [13–16]. Organic sulfides display various
biological activities such as antibacterial and analgesic
[17–19]. Furthermore, a tetrazole fragment can be
RESULTS AND DISCUSSION
A series of 5-{[(1-aryl-1H-1,2,3-triazol-4-yl)-
methyl]sulfanyl)-1-phenyl-1H-tetrazoles 5a–5j were
synthesized starting from phenyl isothiocyanate (1)
which was reacted with sodium azide to gave 1-phenyl-
1H-tetrazole-5-thiol (2). The reaction of 2 with pro-
HO
HN
N
N
O
OH
HN
N
N
N
HO
N
N
N
N
O
N
Cl
N
N
S
NH
N
CH3
HN
S
O
O
OMe
S
O
O
H2N
O
Cl
Azosemide
OH
Me
Latamoxef
Cefamandole
Fig. 1. Active pharmaceutical ingredients containing a tetrazole ring.
1077

THOTLA et al.
1078
Scheme 1.
R
N
N
S
N
S
N
N
N
N
N
N
N
N
NCS
N
N
CH
N
i
ii
iii
N
SH
1
2
3
5a–5j
Reagents and conditionsi: NaN3/H2O, reflux; ii: propargyl bromide, TBAB, Et3N, CH2Cl2, room temp., 3 h; iii: ArN3 (4a–4j),
CuSO4·5H2O, NaAsc, DMF–water, room temp., 4 h. R = Ph (a), 2-MeC6H4 (b), 3-MeC6H4 (c), 4-HOC6H4 (d), 4-ClC6H4 (e),
4-O2NC6H4CH2 (f), 4-MeC(O)C6H4 (g), 2-MeO-4-O2NC6H4 (h), 4-MeO-2-O2NC6H4 (i), cyclohexyl (j).
pargyl bromide afforded propargylsulfanyl derivative
3. Finally, compound 3 was treated with various azides
1 via the click strategy to produce the corresponding
5-{[(1-aryl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-
phenyl-1H-tetrazoles 5a–5i, as well as 5-{[(1-cyclo-
hexyl-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-
phenyl-1H-tetrazole (5j) with excellent yields. The
structures of the products were established on the basis
of spectral analysis data. As an example, the IR spec-
trum of 5a showed characteristic peaks at 1647, 1622,
and 1585 cm–1, which were assigned to N=N, C=C,
Gram-positive Staphylococcus aureus and Bacillus
subtilis, and Gram-negative Pseudomonas aeruginosa
and Escherichia coli, by the paper disc method using
norfloxacin as the standard drug. Compounds 5a, 5d,
5e, and 5i showed a good antibacterial activity against
all the examined bacterial strains, and the remaining
compounds showed a moderate activity (Table 1). The
antifungal activity of 5a–5j was tested in vitro against
two fungal strains (Sclerotium rolfsii and Aspergillus
niger) at a concentration of 1 mg/mL by the disc dif-
fusion method using ketoconazole as reference drug.
Compounds 5d and 5e proved to be more active than
the other tested compounds, but the activity of all of
them was lower than that of ketoconazole (Table 1).
1
and C=N stretchings, respectively. In the H NMR
spectrum of 5a, the 5-H proton of the newly formed
triazole ring resonated at δ 8.29 ppm as a singlet, the
two SCH2 protons resonated at δ 4.77 ppm as a singlet,
and the aromatic proton signals appeared in the region
δ 7.44–7.72 ppm. In the 13C NMR spectrum of 5a, the
following peaks were observed, δC, ppm: 153.7, 143.4,
136.7, 133.4, 130.2, 129.8, 129.7, 128.9, 123.6, 121.8,
120.5, 27.5. The mass spectrum of 5a displayed
[M + H]+ ion peak at m/z 336.
EXPERIMENTAL
All chemicals were purchased from commercial
sources and were used without further purification. The
solvents were dried and distilled prior to use. The
1H and 13C NMR spectra were recorded on a Bruker
Biospin Avance-III spectrometer at 400 and 101 MHz,
respectively, using CDCl3 as solvent and tetramethyl-
Compounds 5a–5j were evaluated for their in vitro
antibacterial activity against four bacterial strains,
Table 1. Antimicrobial activity of 5-{[(1-R-1H-1,2,3-triazol-4-yl)methyl]sulfanyl}-1-phenyl-1H-tetrazoles 5a-5j (inhibition
zone diameter, mm)
Compound no.
S. aureus
19.1
17.8
17.0
21.3
22.0
14.0
16.7
18.0
20.5
13.9
26.6
–
B. subtilis
14.3
12.0
11.7
16.9
18.0
13.7
14.0
16.1
12.4
12.5
19.8
–
P. aeruginosa
22.0
E. coli
15.0
12.2
13.0
16.6
17.0
13.5
18.1
13.6
11.0
12.6
25.7
–
A. niger
8.1
S. rolfsii
9.6
5a
5b
19.0
8.7
8.3
5c
17.8
7.9
7.4
5d
23.3
9.0
11.0
12.5
8.7
5e
22.7
7.3
5f
18.0
5.9
5g
17.7
8.1
6.0
5h
19.1
8.4
8.8
5i
20.3
7.0
8.0
5j
16.5
6.5
7.8
Norfloxacine
Ketoconazole
28.6
–
–
–
11.5
16.6
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SYNTHESIS OF 5-{[(1-ARYL-1H-1,2,3-TRIAZOL-4-YL)METHYL]SULFANYL}-...
1079
silane as reference. Column chromatography was con-
ducted using silica gel (60–120 mesh, Merck). The
reaction progress was monitored by TLC with silica gel
60 F254 plates, and visualization was made under UV
light. The mass spectra were recorded in the ESI
mode with positive ion detection.
7.44 m (4H, Harom), 7.56 m (5H, Harom), 8.02 s
(1H, 5-H). 13C NMR spectrum, δC, ppm: 17.8, 27.6,
123.7, 125.1, 125.9, 126.8, 129.8, 130.2, 131.5, 133.4,
136.2, 142.4, 153.7. Mass spectrum: m/z 350
(Irel 100%) [M + H]+.
5-({[1-(3-Methylphenyl)-1H-1,2,3-triazol-4-yl]-
methyl}sulfanyl)-1-phenyl-1H-tetrazole (5c). Yield
84%, mp 199–202°С. IR spectrum, ν, cm–1: 3055
1-Phenyl-5-(prop-2-yn-1-ylsulfanyl)-1H-tetra-
zole (3). A solution of 1-phenyl-1H-tetrazole-5-thiol
(2, 1 mmol), propargyl bromide (1.2 mmol), and tetra-
butylammonium bromide in a mixture of triethylamine
(2 mL) and methylene chloride (5 mL) was stirred at
room temperature for 3 h. After completion of the
reaction (TLC), the mixture was poured into ice-cold
water, and the solid product was filtered off, dried,
and purified by column chromatography using ethyl
acetate–hexane (8:2). Yield 87%; IR spectrum, ν,
cm–1: 1463 (C–S), 2120 (C≡N). 1H NMR spectrum, δ,
ppm: 2.33 t (1H, J = 2.7 Hz), 4.18 d (2H, J =
2.7 Hz),7.54–7.61 m (5H). 13C NMR spectrum, δC,
ppm: 21.8, 73.1, 76.7, 123.8, 129.9, 130.3, 133.4,
152.8. Mass spectrum: m/z 217 (Irel 100%) [M + H]+.
1
(C–H), 1592 (C=N), 1493 (C–S). H NMR spectrum,
δ, ppm: 2.44 s (3H, CH3), 4.78 d (2H, SCH2, J =
8.1 Hz), 7.24 d (1H, Harom, J = 7.6 Hz), 7.39 t (1H,
Harom, J = 7.8 Hz), 7.45 s (1H, Harom), 7.47–7.58 m
(6H, Harom), 8.26 s (1H, 5-H). 13C NMR spectrum,
δC, ppm: 21.3, 27.5, 117.6, 121.1, 121.8, 123.6,
128.3, 129.0, 129.5, 129.6, 129.8, 130.2, 133.4, 136.7,
140.0, 143.3, 153.8. Mass spectrum: m/z 350
(Irel 100%) [M + H]+.
4-(4-{[(1-Phenyl-1H-tetrazol-5-yl)sulfanyl]-
methyl}-1H-1,2,3-triazol-1-yl)phenol (5d). Yield
94%, mp 193–196°С. IR spectrum, ν, cm–1: 3052
1
(C–H), 1592 (C=N), 1495 (C–S). H NMR spectrum,
δ, ppm: 4.75 s (2H, SCH2), 5.70 s (1H, OH), 6.97 d
(2H, Harom, J = 8.4 Hz), 7.24 d (2H, Harom), 7.55 m
(5H, Harom), 8.17 s (1H, 5-H). 13C NMR spectrum, δC,
ppm: 29.7, 116.4, 122.4, 123.7, 129.8, 130.2, 130.3,
133.4, 136.7, 140.5, 141.8, 152.4. Mass spectrum:
m/z (Irel 100%) [M + H]+.
5-{[(1-Aryl-1H-1,2,3-triazol-4-yl)methyl]sul-
fanyl}-1-phenyl-1H-tetrazoles 5a–5j. A mixture of
tetrazole 3 (1 mmol), azide 4a–4j (1 mmol), CuSO4·
5H2O, and sodium ascorbate in DMF–H2O (5 mL) was
stirred at room temperature for 4 h. After completion of
the reaction (TLC), the mixture was poured into ice-
cold water (20 mL) and extracted with 30 mL of ethyl
acetate. The extract was washed twice with a saturated
solution of ammonium chloride and twice with brine,
dried over Na2SO4, and concentrated under reduced
pressure, and the residue was purified by column
chromatography on silica gel using n-hexane–ethyl
acetate (7:3) as eluent.
5-{[1-(4-Chlorophenyl)-1H-1,2,3-triazol-4-yl)-
methyl]sulfanyl}-1-phenyl-1H-tetrazole (5e). Yield
85%, mp 162–165°С. IR spectrum, ν, cm–1: 3050
1
(C–H), 1592 (C=N), 1497 (C–S). H NMR spectrum,
δ, ppm: 4.76 s (2H, SCH2), 7.47–7.52 d (2H, Harom),
7.53–7.99 m (5H, Harom) 7.66–7.70 d (2H, Harom), 8.28
s (1H, 5-H). 13C NMR spectrum, δC, ppm: 27.4, 121.7,
123.6, 129.9, 130.3, 133.3, 134.7, 135.2, 143.7, 146.8,
153.7. Mass spectrum: m/z 370 (Irel 100%) [M + H]+.
1-Phenyl-5-{[(1-phenyl-1H-1,2,3-triazol-4-yl)-
methyl]sulfanyl}-1H-tetrazole (5a). Yield 86%,
mp 201–204°С. IR spectrum, ν, cm–1: 3050 (C–H),
5-({[1-(4-Nitrobenzyl)-1H-1,2,3-triazol-4-yl]-
methyl}sulfanyl)-1-phenyl-1H-tetrazole (5f). Yield
90%, mp 159–162°С. IR spectrum, ν, cm–1: 3050
1
1595 (C=N), 1497 (C–S). H NMR spectrum, δ, ppm:
4.77 s (2H, SCH2), 7.43 t (1H, Harom, J = 7.4 Hz), 7.49–
7.59 m (7H, Harom), 7.72 d (2H, Harom, J = 7.8 Hz),
8.29 s (1H, 5-H). 13C NMR spectrum, δC, ppm: 27.5,
55.4, 119.2, 120.5, 121.8, 123.6, 128.9, 128.9, 129.7,
129.8, 130.2, 132.5, 133.4, 136.7, 143.4, 153.7. Mass
spectrum: m/z 336 (Irel 100%) [M + H]+.
1
(C–H), 1592 (C=N), 1496 (C–S). H NMR spectrum,
δ, ppm: 4.67 s (2H, SCH2), 5.61 s (2H, NCH2), 7.40–
7.42 d (2H, Harom), 7.50–7.60 m (5H, Harom), 7.89 s
(1H, 5-H), 8.23–8.25 d (2H, Harom). 13C NMR spec-
trum, δC, ppm: 27.4, 53.1, 121.5, 123.6, 124.3, 128.6,
129.9, 130.3, 133.3, 141.4, 148.0, 153.7. Mass spec-
trum: m/z 395 (Irel %) [M + H]+.
5-({[1-(4-Methylphenyl)-1H-1,2,3-triazol-4-yl]-
methyl}sulfanyl)-1-phenyl-1H-tetrazole (5b). Yield
90%, mp 214-217°С. IR spectrum, ν, cm–1: 3051
1-[4-(4-{[(1-Phenyl-1H-tetrazol-5-yl)sulfanyl]-
methyl}-1H-1.2.3-triazol-1-yl)phenyl]ethanone (5g).
Yield 85%, mp 188–191°С. IR spectrum. ν. cm–1: 3053
1
(C–H), 1595 (C=N), 1498 (C–S). H NMR spectrum,
δC, ppm: 2.19 s (3H, CH3), 4.79 s (2H, SCH2), 7.29–
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 56 No. 6 2020

THOTLA et al.
1080
1
(C–H), 1596 (C=N), 1496 (C–S). H NMR spectrum,
δ, ppm: 2.66 s (3H, CH3), 4.77 s (2H, SCH2), 7.53–
7.61 m (4H, Harom), 7.83–7.90 m (5H, Harom),
7.89 s (1H, 5-H). 13C NMR, δC, ppm: 26.7, 29.7, 120.1,
122.8, 123.6, 125.5, 129.9, 128.9, 130.8, 133.3, 136.9,
139.8, 153.7, 196.6. Mass spectrum: m/z 398
(Irel 100%) [M + H]+.
FUNDING
K. Thotla thanks the Council of Scientific and Industrial
Research (CSIR, New Delhi, India) for financial support in
the form of fellowship.
CONFLICT OF INTEREST
The authors declare no conflict of interest.
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5-({[1-(2-Methoxy-4-nitrophenyl)-1H-1,2,3-tri-
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SYNTHESIS OF 5-{[(1-ARYL-1H-1,2,3-TRIAZOL-4-YL)METHYL]SULFANYL}-...
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