Synthesis and spectral characterization of some new thiazolyl-pyrazolines bearing 1,2,4-triazole moiety

Article abstract of DOI:10.1080/10426507.2010.497519

Chemical Equation Presented In this study, several new 1-(4-aryl-5- triazolyl-2-thiazolyl)-3,5-diaryl-2-pyrazolines (3a-r) were synthesized by reacting 3,5-diaryl1-thiocarbamoyl-2-pyrazolines (1) with 2-bromo-1-aryl-2-(1H- 1,2,4-triazol-1-yl) ethanones (2) in boiling ethanol. The chemical structures of the compounds were verified by IR, 1H NMR, ESI-MS spectroscopic data, and elemental analyses. Copyright Taylor & Francis Group, LLC.

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Phosphorus, Sulfur, and Silicon and the
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Synthesis and Spectral Characterization
of Some New Thiazolyl-Pyrazolines
Bearing 1,2,4-Triazole Moiety
Sheng-Qin Chen a , Yi-Chao Zhang b & Fang-Ming Liu a
a College of Materials and Chemical Engineering, Hangzhou Normal
University, Hangzhou, P.R. China
b WuXi PharmaTech Co., Ltd, Shanghai, P.R. China
Version of record first published: 19 Feb 2011.
To cite this article: Sheng-Qin Chen , Yi-Chao Zhang & Fang-Ming Liu (2011): Synthesis and Spectral
Characterization of Some New Thiazolyl-Pyrazolines Bearing 1,2,4-Triazole Moiety, Phosphorus, Sulfur,
and Silicon and the Related Elements, 186:2, 319-325
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Phosphorus, Sulfur, and Silicon, 186:319–325, 2011
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2010.497519
SYNTHESIS AND SPECTRAL CHARACTERIZATION
OF SOME NEW THIAZOLYL-PYRAZOLINES BEARING
1,2,4-TRIAZOLE MOIETY
Sheng-Qin Chen,1 Yi-Chao Zhang,2 and Fang-Ming Liu1
1College of Materials and Chemical Engineering, Hangzhou Normal University,
Hangzhou, P.R. China
2WuXi PharmaTech Co., Ltd, Shanghai, P.R. China
GRAPHICAL ABSTRACT
S
S
O
N
H2N
N
NH2
R1
NH2
R2
N
R3
H
N
N
R2
N
KOH/EtOH
R1
S
1
N
EtOH
N
R1
N
N
N
O
N
N
O
NaAc / HAC
Br2
R3
N
R3
R2
N
Br
2
3a-r
Abstract In this study, several new 1-(4-aryl-5-triazolyl-2-thiazolyl)-3,5-diaryl-2-pyrazolines
(3a–r) were synthesized by reacting 3,5-diaryl1-thiocarbamoyl-2-pyrazolines (1) with 2-bromo-
1-aryl-2-(1H-1,2,4-triazol-1-yl) ethanones (2) in boiling ethanol. The chemical structures of the
compounds were verified by IR, 1H NMR, ESI-MS spectroscopic data, and elemental analyses.
Keywords Carbothioamide; pyrazoline; thiazole; 1,2,4-triazole
INTRODUCTION
1,2,4-Triazole derivatives are of great interest in the medicinal and agricultural
fields due to their broad spectrum pharmacological activities, such as insecticidal, antifun-
gal, antibacterial, anti-HIV, COX-2 inhibitor, anticonvulsant, and plant growth regulative
properties,1–6 and quite a few of them have become commercial products (i.e., flucona-
zole, itraconazole).7,8 Similarly, thiazole and pyrazoline derivatives are also well known
nitrogen-containing heterocyclic compounds, which exhibit a large number of biological
activities.9–18 It was therefore of interest to combine these potential biologically active units
to give fused derivatives.
Received 12 April 2010; accepted 27 May 2010.
Address correspondence to Fang-Ming Liu, College of Materials and Chemical Engineering, Hangzhou
Normal University, Hangzhou 310036, P.R. China. E-mail: fmliu859@sohu.com
319

320
S.-Q. CHEN ET AL.
A literature survey showed that thiazole compounds containing both the 1,2,4-triazole
group and the pyrazoline group in a single molecule have not been reported so far. Encour-
aged by these facts, and in continuation of our interest in the synthesis of chemically and
biologically important heterocycles containing the 1,2,4-triazole moiety,19 a series of novel
heterocyclic compounds including 1,2,4-triazole, pyrazoline, and thiazole (3a–r) were syn-
thesized, which might exhibit enhanced activities owing to the incorporation of different
pharmacophores into their structures.
RESULTS AND DISCUSSION
The synthetic routes leading to the desired compounds are shown in Scheme 1.
1,3-Diaryl-2-propenones (chalcones) were readily obtained by the reaction of aromatic
aldehydes and 1-arylethanones by a Claisen–Schmidt condensation reaction in good yield.
The chalcones were subsequently reacted with thiosemicarbazide in the presence of sodium
hydroxide in ethanol, to give 1-thiocarbamoyl-3,5-diphenyl-pyrazoline derivatives (1) ac-
cording to the methods described in the literature.15,20–22
S
S
O
N
H2N
N
H
NH2
R1
NH2
R2
N
R3
N
N
R2
N
KOH/EtOH
R1
S
1
N
EtOH
N
R1
N
N
N
O
N
N
O
NaAc / HAC
Br2
R3
N
R3
R2
N
Br
3a-r
2
(3j) R1=Cl,R2=R3=H
(3k) R1=R3=Cl,R2=H
(3a) R1=R2=R3=H
(3b) R1=R2=H,R3=Cl
(3l) R1=Cl,R2=H,R3=OCH3
(3m) R1=R2=Cl,R3=H
(3n) R1=R2=R3=Cl
(3c) R1=R2=H,R3=OCH3
(3d) R1=R3=H,R2=Cl
(3e) R1=H,R2=R3=Cl
(3o) R1=R2=Cl,R3=OCH3
(3p) R1=Cl,R2=OCH3,R3=H
(3f) R1=H,R2=Cl,R3=OCH3
(3g) R1=R3=H,R2=OCH3
(3q) R1=R3=Cl,R2=OCH3
(3r) R1=Cl,R2=R3=OCH3
(3h) R1=H,R2=OCH3,R3=Cl
(3e) R1=H,R2=R3=OCH3
Scheme 1
2-Bromo-1-arylethanones, prepared by the reaction of 1-arylethanones with bromine
in anhydrous ether, reacted with 1H-1,2,4-triazole in the presence of triethylamine in
acetone to give 1-aryl-2-(1H-1,2,4-triazol-1-yl)-ethanone, which was brominated in the
presence of sodium acetate/acetic acid to afford the corresponding 2-bromo-1-aryl-2-(1H-
1,2,4-triazol-1-yl)-ethanones (2).23,24
The condensation of 2-bromo-1-arylethanones (2) with pyrazolines (1) in refluxing
ethanol resulted in the formation of the desired cyclized products 2-(3,5-diaryl-4,5-dihydro-
1H-pyrazol-1-yl)-4-aryl-5-(1H-1,2,4-triazol-1-yl) thiazoles (3a–r, Table 1) in 75–95%

NEW THIAZOLYL-PYRAZOLINES
321
Table 1 Physical data of compounds (3a–r)
(%) Analyses, Calcd./Found
Molecular
formula
Yield
(%)
Mp,
◦C
Compound
no.
N
H
C
18.74/18.78
17.40/17.34
17.56/17.52
17.40/17.51
16.24/16.33
16.38/16.45
17.56/17.63
16.38/16.43
16.52/16.55
17.40/17.44
16.24/16.20
16.38/16.43
16.24/16.27
15.23/15.27
15.35/15.33
16.38/16.44
15.35/15.41
15.48/15.44
4.49/4.48
3.97/4.01
4.63/4.57
3.97/4.00
3.51/3.56
4.13/4.03
4.63/4.67
4.13/4.08
4.76/4.65
3.97/3.88
3.51/3.54
4.13/4.21
3.51/3.62
3.10/3.14
3.68/3.72
4.13/4.12
3.68/3.63
4.27/4.22
69.62/69.57
64.66/64.69
67.76/67.79
64.66/64.71
60.35/60.28
63.21/63.33
67.76/67.68
63.21/63.32
66.12/66.23
64.66/64.72
60.35/60.32
63.21/63.27
60.35/60.42
56.58/56.59
59.24/59.41
63.21/63.28
59.24/59.33
61.93/61.99
C26H20N6S
92
90
94
80
80
89
94
90
94
88
81
92
80
76
84
90
84
93
110–112
182–183
170–171
176–177
213–214
116–117
171–173
176–177
175–177
198–199
213–214
163–164
204–205
256–258
214–215
192–193
208–210
241–242
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
3k
3l
3m
3n
3o
3p
3q
3r
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
C
26H19ClN6S
27H22N6OS
26H19ClN6S
26H18Cl2N6S
27H21ClN6OS
27H22N6OS
27H21ClN6OS
28H24N6O2S
26H19ClN6S
26H18Cl2N6S
27H21ClN6OS
26H18Cl2N6S
26H17Cl3N6S
27H20Cl2N6OS
27H21ClN6OS
27H20Cl2N6OS
28H23ClN6O2S
yield. The progress of each reaction was monitored by thin layer chromatography. Com-
1
pounds (3a–r) were characterized by IR, H NMR spectroscopy, and mass spectrometry
(Scheme 1).
1
The IR spectral, mass spectra, and H NMR spectral data gave strong evidence for
the structures of 3a–r (Table 2). The IR spectra of 3a–r exhibit bands at 1631–1632
cm−1(C N). In addition, their 1H NMR spectra revealed a multiplet between δ 7.79–6.73
ppm due to the protons of aromatic rings, the signal for 1,2,4-triazole, and methoxyl
appeared at δ 8.19–8.06 ppm and δ 3.82–3.74 ppm, respectively. Three distinct double
of doublets of the ABX system (a CH proton and two anisochronous protons of a CH2)
appeared at δ 5.71–3.29 ppm, as has been observed in the pyrazoline ring.15 The EI mass
spectra of compounds 3a–r revealed the existence of the molecular ion peaks and anticipated
fragmentation peaks, which were in good agreement with the given structures of products.
For example, the mass spectrum of 3a had molecular ion peaks at m/z 448 (100%), 380 (M-
C2H2N3 2%), 221 (M-C6H5C2H2N3C3NS 78%), 117 (C6H5CN2 23%), 104 (C6H5C2H3
77%), 77 (C6H5 49%), consistent with the molecular formula.
The chapped mechanism of the mass spectrum is showed in Figure 1. The IR spectrum
of compound 3i showed the stretching band of C N at 1632 cm−1, and its 1H NMR spectrum
showed the signals of Ha, Hb, Hx of pyrazoline ring as doublet of doublets in the regions
3.40–3.35 ppm (Ha) and 3.96–3.88 ppm (Hb). The CH (Hx) proton appeared as a doublet of
doublets at 5.70–5.65 ppm due to vicinal coupling with the two magnetically nonequivalent
protons of the methylene group at position 4 of pyrazoline ring (Jab = 17.60, Jax = 12.01,
1
and Jbx = 5.99 Hz). Two sharp singlets showed at δ 3.81ppm and δ 3.76 ppm in the H
NMR spectrum due to its methoxyl protons. The remaining 13 aromatic protons resonated
as multiplets in the range δ 7.78–6.73.15

322
S.-Q. CHEN ET AL.
Table 2 IR (cm−1), 1H NMR (δppm), and mass spectral data of compounds (3a–r)
Compound IR (cm−1
)
MS(EI):
m/z(M+)
no.
C
N
1H NMR(CDCl3)
3a
1631
δ 8.06,8.19(2H,2s,Triazole-H),6.96–7.73(15H,m,phenyl-H), 5.71
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.0Hz), 3.95 (dd,1H,C4-Ha,Jax
448
482
478
=
12.0Hz,Jab = 17.60Hz),3.39(dd,1H,C4-Hb,Jbx = 6.0Hz,Jab = 17.6Hz).
3b
3c
1631
1632
δ 8.06,8.19(2H,2s,Triazole-H),7.00–7.77(14H,m,phenyl-H), 5.69
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.3Hz), 3.93 (dd,1H,C4-Ha,Jax
=
12.0Hz,Jab = 17.6Hz),3.31(dd,1H,C4-Hb,Jbx = 6.3Hz,Jab = 17.6Hz).
δ 8.06,8.19(2H,2s,Triazole-H),7.03–7.79(14H,m,phenyl-H), 5.68
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.33Hz), 3.92 (dd,1H,C4-Ha,Jax
=
12.0Hz,Jab = 17.6Hz), 3.75(3H,s,CH3O), 3.30(dd,1H,C4-Hb,Jbx
6.3Hz,Jab = 17.6Hz).
=
3d
3e
3f
1631
1632
1632
δ 8.06,8.18(2H,2s,Triazole-H),7.01–7.70(14H,m,phenyl-H), 5.71
482
516
512
(dd,1H,C5-Hx,Jax = 11.9Hz,Jbx = 6.4Hz), 3.89 (dd,1H,C4-Ha,Jax
=
11.9Hz,Jab = 17.6Hz),3.38(dd,1H,C4-Hb,Jbx = 6.42Hz,Jab = 17.6Hz).
δ 8.06,8.18(2H,2s,Triazole-H),6.98–7.76(13H,m,phenyl-H), 5.70
(dd,1H,C5-Hx,Jax = 12.00Hz,Jbx = 6.4Hz), 3.90 (dd,1H,C4-Ha,Jax
=
12.00Hz,Jab = 17.6Hz),3.40(dd,1H,C4-Hb,Jbx = 6.4Hz,Jab = 17.60Hz).
δ 8.06,8.18(2H,2s,Triazole-H),7.00–7.77(13H,m,phenyl-H), 5.68
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.0Hz), 3.91 (dd,1H,C4-Ha,Jax
=
=
=
=
=
12.0Hz,Jab = 17.6Hz), 3.76(3H,s,CH3O), 3.37(dd,1H,C4-Hb,Jbx
6.0Hz,Jab = 17.6Hz).
=
3g
3h
3i
1631
1631
1632
δ 8.06,8.16(2H,2s,Triazole-H),6.74–7.79(14H,m,phenyl-H), 5.71
(dd,1H,C5-Hx,Jax = 11.9Hz,Jbx = 6.2Hz), 3.93 (dd,1H,C4-Ha,Jax
478
512
508
11.9Hz,Jab = 17.6Hz), 3.82(3H,s,CH3O), 3.35(dd,1H,C4-Hb,Jbx
6.2Hz,Jab = 17.6Hz).
=
δ 8.06,8.16(2H,2s,Triazole-H),7.00–7.79(13H,m,phenyl-H), 5.67
(dd,1H,C5-Hx,Jax = 11.9Hz,Jbx = 6.3Hz), 3.94 (dd,1H,C4-Ha,Jax
11.9Hz,Jab = 17.6Hz), 3.80(3H,s,CH3O), 3.32(dd,1H,C4-Hb,Jbx
6.3Hz,Jab = 17.6Hz).
=
δ 8.06,8.16(2H,2s,Triazole-H),6.73–7.78(13H,m,phenyl-H), 5.67
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.0Hz), 3.92 (dd,1H,C4-Ha,Jax
12.0Hz,Jab = 17.6Hz),3.81(3H,s,CH3O), 3.76(3H,s,CH3O),3.38
(dd,1H,C4-Hb,Jbx = 6.0Hz, Jab = 17.6Hz).
3j
3k
3l
1632
1631
1632
δ 8.06,8.19(2H,2s,Triazole-H),6.89–7.70(14H,m,phenyl-H), 5.68
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.0Hz), 3.95 (dd,1H,C4-Ha,Jax
482
516
512
12.0Hz,Jab = 17.6Hz),3.39(dd,1H,C4-Hb,Jbx = 6.0Hz, Jab = 17.6Hz).
δ 8.06,8.19(2H,2s,Triazole-H),7.00–7.70(13H,m,phenyl-H), 5.71
(dd,1H,C5-Hx,Jax = 11.9Hz,Jbx = 6.1Hz), 3.94 (dd,1H,C4-Ha,Jax
=
11.9Hz,Jab = 17.6Hz),3.37(dd,1H,C4-Hb,Jbx = 6.1Hz,Jab = 17.6Hz).
δ 8.06,8.19(2H,2s,Triazole-H),7.00–7.71(13H,m,phenyl-H), 5.66
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.2Hz), 3.91 (dd,1H,C4-Ha,Jax
=
=
12.0Hz,Jab = 17.6Hz), 3.74(3H,s,CH3O), 3.38(dd,1H,C4-Hb,Jbx
6.2Hz,Jab = 17.6Hz).
=
3m
3n
3o
1631
1632
1631
δ 8.06,8.16(2H,2s,Triazole-H),6.82–7.70(13H,m,phenyl-H) ,5.69
(dd,1H,C5-Hx,Jax = 11.9Hz,Jbx = 6.0Hz), 3.94 (dd,1H,C4-Ha,Jax
516
552
546
11.9Hz,Jab = 17.6Hz),3.32(dd,1H,C4-Hb,Jbx = 6.0Hz,Jab = 17.6Hz).
δ 8.06,8.16(2H,2s,Triazole-H),6.75–7.70(12H,m,phenyl-H) ,5.71
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.0Hz), 3.90 (dd,1H,C4-Ha,Jax
=
12.0Hz,Jab = 17.6Hz),3.29(dd,1H,C4-Hb,Jbx = 6.0Hz,Jab = 17.6Hz).
δ 8.06,8.16(2H,2s,Triazole-H),6.73–7.69(12H,m,phenyl-H), 5.70
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.4Hz), 3.92 (dd,1H,C4-Ha,Jax
=
12.0Hz,Jab = 17.6Hz), 3.76(3H,s,CH3O), 3.30(dd,1H,C4-Hb,Jbx
6.4Hz,Jab = 17.6Hz).
=

NEW THIAZOLYL-PYRAZOLINES
323
Table 2 IR (cm−1), 1H NMR (δppm), and mass spectral data of compounds (3a–r) (Continued)
Compound IR(cm−1
)
MS(EI):
m/z(M+)
no.
C
N
1H NMR(CDCl3)
3p
1631
δ 8.06,8.17(2H,2s,Triazole-H),6.83–7.69(13H,m,phenyl-H), 5.71
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.4Hz), 3.89 (dd,1H,C4-Ha,Jax
512
546
542
=
=
=
12.0Hz,Jab = 17.6Hz), 3.80(3H,s,CH3O), 3.29(dd,1H,C4-Hb,Jbx
6.4Hz,Jab = 17.6Hz).
=
3q
3r
1632
1631
δ 8.06,8.17(2H,2s,Triazole-H),6.89–7.70(12H,m,phenyl-H), 5.67
(dd,1H,C5-Hx,Jax = 12.0Hz,Jbx = 6.0Hz), 3.90 (dd,1H,C4-Ha,Jax
12.0Hz,Jab = 17.6Hz), 3.81(3H,s,CH3O), 3.35(dd,1H,C4-Hb,Jbx
6.0Hz,Jab = 17.6Hz).
=
δ 8.06,8.17(2H,2s,Triazole-H),6.81–7.69(12H,m,phenyl-H), 5.68
(dd,1H,C5-Hx,Jax = 11.9Hz,Jbx = 6.0Hz), 3.91 (dd,1H,C4-Ha,Jax
11.9Hz,Jab = 17.6Hz),3.82(3H,s,CH3O),
3.74(3H,s,CH3O),3.34(dd,1H,C4-Hb,Jbx = 6.0Hz,Jab = 17.6Hz).
EXPERIMENTAL
Melting points were recorded on a Mettler FP-5 capillary melting point apparatus
and are uncorrected. Elemental analyses were recorded on a Perkin-Elmer 2400 elemental
analyzer. The IR spectra were determined as potassium bromide pellets on a Bruker Equinox
1
55 FT-IR spectrophotometer. The H NMR spectra were recorded on a Varian Inova-400
N
N
N
N
N
S
S
N
N
N
N
N
N
N
m/z:380
m/z:448
N
N
N
S
m/z:117
N
C2H4
m/z:77
N
N
N
m/z:221
m/z:104
Figure 1 Synthesis of compound 3a.

324
S.-Q. CHEN ET AL.
spectrophotometer using TMS as an internal standard. EI-MS spectra were obtained with
an Agilent 5975 apparatus.
1-Thiocarbamoyl-3,5-diphenyl-pyrazoline derivatives (1) were prepared according to
the reported methods.15,20–22 Triazolylethanones and bromine substituted triazolylethanones
(2) were prepared according to the reported methods.23,24
General Procedure (3a–3r): Synthesis of 2-(3,5-Diphenyl-4,5-dihydro-1H-
pyrazol-1-yl)-4-phenyl-5-(1H-1,2,4-triazol-1-yl)-thiazole (3a)
A mixture of 3,5-diphenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide (0.5 mmol)
and 2-bromo-1-phenyl-2-(1H-1,2,4-triazol-1-yl) ethanone (0.5 mmol) in ethanol (30 mL)
was heated under reflux for 0.5 h. Upon standing the reaction mixture at 25◦C, the crude
product (3a) separated, which was filtered, washed with cold ethanol, dried, and recrystal-
lized From ethanol.
Compounds (3b–r) were obtained using the same procedure (Scheme 1). The physical
data of the compounds prepared (3a–r) are shown in Table 1.
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