Synthesis and antimicrobial studies of new bis[4,5-dihydro-1-phenyl-5- thienyl-3-(phenyl-4-alkoxy)-1H-pyrazole] derivatives

Article abstract of DOI:10.1002/jhet.1805

Syntheses and antimicrobial behavior of the alkyl linked new bispyrazolines 4a-4g have been investigated. These compounds exhibited better antimicrobial activities as compared with their corresponding bischalcones. The structures of the prepared compounds

Full text of DOI:10.1002/jhet.1805

1162
Synthesis and Antimicrobial Studies of New Bis[4,5-dihydro-1-phenyl-5-
Vol 51
thienyl-3-(phenyl-4-alkoxy)-1H-pyrazole] Derivatives
*
Mohamad Yusuf and Payal Jain
Department of Chemistry, Punjabi University, Patiala-147002, Punjab, India
*
E-mail: yusuf_sah04@yahoo.co.in
Received May 9, 2012
DOI 10.1002/jhet.1805
Published online 16 December 2013 in Wiley Online Library (wileyonlinelibrary.com).
3'''
O
CH2
(CH2)n
CH2
O
4'''
5'''
2'''
1'''
H
M
H
M
3''
4''
3
H
H
A
4
6'''
N
5
2
N
5''
2''
H
N
X
S
N1
1'
S
1''
H
2'
6'
5'
3'
4a-4g
n = 1, 2, 3, 4, 6, 8,10
Syntheses and antimicrobial behavior of the alkyl linked new bispyrazolines 4a–4g have been investi-
gated. These compounds exhibited better antimicrobial activities as compared with their corresponding
bischalcones. The structures of the prepared compounds (3a–3g and 4a–4g) were determined from the
1
rigorous analysis of their IR, H NMR, 13C NMR, and mass spectral parameters.
J. Heterocyclic Chem., 51, 1162 (2014).
INTRODUCTION
RESULTS AND DISCUSSION
The chalcones are the important molecules that constitute
the part of various naturally occurring and biologically sig-
nificant products [1]. These compounds are generally
obtained from the aldol condensation and Claisen–Schimdt
reactions of the carbonyl compounds [2]. It is observed that
most of the chalcones have pharmaceutical and medicinal
applications [3]. These substrates are found to be effective
as anticancer [4], antiviral [5], cardiovascular [6], and anti-
inflammatory [7] agents. The reactions of these intermediates
with suitable hydrazine derivative lead to the generation of
five-membered pyrazoline compounds. The synthesis of
pyrazoline derivatives has been studied because of their wide
range of biological activities such as antitumor [8,9], immu-
nosuppressive [10], antimicrobial [11], antifungal [12], and
anti-inflammatory [13]. Bispyrazolines are the bichromopho-
ric molecules that are formed by the linking two pyrazoline
moieties together through the carbon chains, and some
of the results have been reported upon the synthesis of bis-
pyrazolines [14]. It is evident from the literature that very
little attention has been focussed upon the compounds
involving the internal chains of varying lengths. By consider-
ing these aspects in view, we report herein the synthesis
and antimicrobial evaluations of new bispyrazolines 4a–4g
built around the aliphatic chains consisting of 3–12 methy-
lene groups.
The bispyrazolines 4a–4g required for the present
investigations were synthesized starting from the Claisen–
Schmidt reaction of 4-hydroxyacetophenone with 2-
thiophenecarbaxaldehyde 1, which yielded chalcone 2. The
O-alkylation of later with suitable 1,o-dibromoalkanes
in the presence K2CO3, dry acetone, and tetrabutyl ammo-
nium iodide (PTC) provided bischalcones 3a–3g in good
yields. The cyclization of 3a–3g with phenyl hydrazine
under alcoholic conditions led to the formation of bispyra-
zolines 4a–4g, which were crystallized from CH3OH to
give pure compounds in moderate yields (Scheme 1). The
use of PTC in the aforementioned synthesis not only
reduced the reaction times drastically but also improved
the yield of bischalcones. The structures of the prepared
compounds (3a–3g and 4a–4g) were determined from the
1
rigorous analysis of their IR, H NMR, 13C NMR, and
mass spectral parameters. The elemental analysis results also
confirmed the purity of the prepared products.
IR spectra of bischalcones 3a–3g showed C═O and C═C
group absorptions at 1661–1652 and 1602–1594 cmꢀ1
,
respectively. Other significant bands were observed at
2940-2920, 2878-2852 (methylene C–H), 1245-1236 and
1
1034-1020 (C–O) cmꢀ1. In the H NMR spectra of these
compounds, the doublets resonating at d 7.94-7.83 and 7.52-
7.32 could be assigned to H-3 and H-2 protons, respectively,
© 2013 HeteroCorporation

July 2014
Synthesis of New Bis[4,5-dihydro-1-phenyl-5-thienyl-3-(phenyl-4-alkoxy)-
1H-pyrazole]derivatives
1163
Scheme 1
3 '
3''
4''
HO
4 '
HO
2 '
a
2
+
2 ''
5 ''
5 '
1
CHO
CH3
1'
S
S
6 '
3
1''
O
2
O
1
b
3'
O
CH2
( CH2)n
CH2
O
4'
5'
2'
1'
4''
3''
2
1
5''
S
6'
2''
3
S
1''
O
O
3a-3g
c
3'''
6'''
O
CH2
(CH2)n
CH2
O
4'''
5'''
2'''
HM
HA
4HM
1'''
3H'' A
3
4''
N
2
N
5''
5
HX1
2''
N
HX
S
N
1'
S
1''
2'
3'
6'
5'
4'
4a-4g
n = 1, 2, 3, 4, 6, 8,10
and the coupling value of 15.3–14.5 Hz between theses
hydrogens describes the trans geometry around the C-2 and
C-3 double bond. The two doublets in the range of d 8.02–
7.99 (Jo =8.8–8.2 Hz) and 7.03–6.96 (Jo =8.8–8.2 Hz) could
be appearing because of the aromatic protons H-20,60 and
H-30,50, respectively. The signals of internal chain OCH2
group protons were found to be resonating at d 4.29–4.03
(t, Jvic = 6.6–5.8 Hz), and the remaining (CH2)n group hydro-
gens produced suitable signals at d 2.57–1.33 with suitable
multiplicities. In the 13C NMR spectra of 3a–3g, the inter-
nal chain methylene groups were resonating at d 68.13–
67.28 (OCH2) and 29.64–25.00 {(CH2)n}; the downfield
resonances of the former suggest their placement near an
electronegative oxygen atom. Other significant signals were
found to be placed at d 186.86–186.60, 120.33–120.05, and
140.68–139.78, which could be attributed to C-1, C-2, and
C-3 of the enone moiety.
IR spectra of 4a–4g did not reveal any absorption in the
region of 1661–1652 cmꢀ1, which describes the absence of
C═O group in these compounds, and here, major bands
were observed in the region at 1599–1592 cmꢀ1 because
of the C═N group. In the 1H NMR spectra of these
compounds, the signals corresponding to the double bond
hydrogens (H-2 and 3) at d 7.94–7.83 and 7.52–7.32 of
the bischalcones 3a–3g were found missing altogether,
which indicates the involvement of the enone moiety
during the cyclization reaction. The pyrazoline ring
protons H-X, H-M, and H-A resulted in suitable reso-
nances at d 5.67–5.56 (2H, dd), 3.86–3.81 (2H, dd), and
3.24–3.19 (2H, dd), respectively. The remaining hydro-
gens were found to be resonating at the suitable positions
(see Experimental section).
In the 13C NMR spectra of 4a–4g, signals belonging to the
C═O group of bischalcones at d 186.86–186.60 were found
to be absent, which also corroborates the transformation of
this functionality (C═O) in the formation of pyrazoline
moiety. The pyrazoline ring carbons C-3, C-4, and C-5
were resonating at d 156.23–154.26, 43.62–43.25, and
59.74–59.41, respectively. The remaining carbon atoms
were found to be present at the expected positions
(see Experimental section). ESI–MS spectra of 4a–4g also
corroborated the proposed structures, which exhibited
molecular ions at the appropriate m/z values (see Experimen-
tal section).
The stereochemical features of pyrazoline ring in 4a–4g
were determined from the considerations of coupling
constants (J). The vicinal coupling constant (3 J) between
H-X and H-M was found to be 12.2–11.8 Hz, which reflects
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

1164
M. Yusuf and P. Jain
Vol 51
that these hydrogens are cis to each other, whereas coupling
value of JXA = 6.9–6.2 Hz and JMA = 17.4–16.5 Hz describes
the trans relationship between H-X and H-A, whereas H-M
and H-A are geminally placed at C-40. The aryl rings placed
at N-1 and C-5 are evidently trans oriented to avoid any
intramolecular repulsion.
The compounds 3d–3g were found to be active
(MIC–12.5 mg/mL) against the strains P. fluorescens
and S. pyrogens, whereas the compounds 3c–3f were found
to be active for fungal strain F. oxysporum. The similar
activity was exhibited by 3d and 3g against most of the tested
microorganisms (Table 1).
Mechanistically, the cyclization reactions described earlier,
that is, 3a–3g ! 4a–4g can be visualized as having occurred
through an initial nucleophilic attack (path a) of phenyl
hydrazine upon the carbonyl group of enone moiety under
the influence of proton followed by dehydration to produce
hydrazones 3a0–3g0. The later further undergoes cyclization
reaction with the addition of proton to give 4a–4g as the
end products (Scheme 2).
In other way, phenyl hydrazine could also undergo attack
upon the enone part of 3a–3g in a Michael addition fashion
(path b) to give 3a00–3g00 as the intermediate, which
subsequently might suffer cyclization reaction followed by
dehydration to give 5a–5g.
In spite of our repeated and best efforts, we were not able
to isolate any product similar to 5a–5g, and the only products
obtained were 4a–4g. Thus, in bischalcone 3a–3g, direct
condensation of phenyl hydrazine with carbonyl group (path
a) is the preferred pathway over the Michael addition (path b,
Scheme 2).
It is evident from Table 2 that the compounds 4c–4g were
found to be active against the bacteria strain (P. fluorescens)
and fungi stains (P. glabrum and F. oxysporum) and
the bispyrazolines 4f and 4g linked through 10, and 12
methylene group chains showed better activity as compared
with other compounds (Table 2).
CONCLUSION
It may be concluded that this study describes the general
method for the synthesis of new bispyrazolines linked
through the 3-aryl ring under the normal conditions. The
bispyrazolines seem to be better antimicrobial agents than
the corresponding bischalcones.
EXPERIMENTAL
Melting points reported are uncorrected. IR (Buckinghamshire,
England) spectra were scanned in KBr pellets on a Perkin-Elmer
1
RXIFT Infrared spectrophotometer. H NMR (Fallanden, Switzer-
Antimicrobial evaluation. All cultures were obtained
from MTCC (Microbial Type Culture Collection & Gene
Bank, Chandigarh-160036, India). The newly prepared
compounds (3a–3g and 4a–4g) were screened for their
antimicrobial activities in vitro against seven bacterial strains
namely Klubsellia pneumoniae (MTCC 3384), Pseudomonas
aeruginosa (MTCC 424), Escherichia coli (MTCC 443),
Staphylococcus aureus (MTCC 96), Bacillius subtilis
(MTCC 441), Pseudomonas fluorescens (MTCC 103),
Streptococcus pyrogens (MTCC 442), and five fungi strains
Aspergillius janus (MTCC 2751), Aspergillius niger (MTCC
281), Fusarium oxysporum (MTCC 2480), Aspergillus
sclerotiorum (MTCC 1008) and Pencillium glabrum (MTCC
4951). Amoxicillin and fluconazole were used as reference
drugs for comparison. All the bacterial strains were grown at
37ꢁC for 24 h in nutrient broth, and fungi strains were grown
in malt extract at 28ꢁC for 72 h. Each test compound was
dissolved in DMSO. MIC of all the compounds (3a–3g and
4a–4g) were evaluated by using serial tube dilution methods
[15] at various concentration of 100, 50, 25, 12.5, 6.25, and
3.12 mg/mL, and MIC thus obtained were compared with the
control (amoxicillin and fluconazole).
land) spectra were recorded on a 400 MHz Bruker spectrometer using
TMS as the internal standard. The mass spectra (Vernon Hills, USA)
have been scanned on the Waters Micromass Q-T of Micro (ESI)
spectrometer. TLC plates were coated with silica gel suspended in
MeOH–CHCl3, and iodine vapors were used as visualizing agent.
Synthesis of (2E)-1-(4-hydroxyphenyl)-3-(thiophene-2-yl)
prop-2-en-1-one 2a.
A mixture of 4-hydroxyacetophenone
(4.0 g, 0.02941 mol), 2-thiophenecarboxaldehyde (3.29 g, 0.02941 mol),
and NaOH (1.0 g, 0.024 mol) in ethanol (25.0 mL) was stirred in
an ice bath for 10 h. During the course of reaction, the initially
formed greenish mixture changed to a reddish gummy mass. The
resulting reaction mixture was poured into iced HCl to provide a
yellow solid that was filtered, thoroughly washed with water, and
dried. The crude material thus obtained was recrystallized from
MeOH:CHCl3 (3:1) to obtain a pure solid 2a.
2a: yellow needles, yield 65%; mp: 166–168ꢁC. IR (KBr) cmꢀ1
:
3469 (OH), 1688 (C═O), 1600 (C═C); 1H NMR (400MHz,
CDCl3): d 10.25 (1H, s, OH), 7.96 (1H, d, Jtrans = 15.1 Hz, H-3), 7.82
(2H, d, J = 3.2 Hz, H-2’, 60), 7.60 (1H, d, Jtrans = 15.1Hz, H-2),
7.52 (2H, d, J = 2.6Hz, H-30, 50), 7.43 (1H, d, J = 1.5Hz, H-300),
7.12 (1H, d, J = 3.6Hz, H-500), 6.89 (1H, d, J =2.4 Hz, H-400).
MS (ESI): m/z (M)+ 230. Anal. Calcd for C13H10O2S: C, 67.82%;
H, 4.34%; S, 13.91%; found: C, 67.70%; H, 4.21%; S, 13.80%.
Synthesis of (2E,20E)-1,10-(4,40-(propane-1,3-diylbis(oxy))bis
(4,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one 3a.
A
suspension of chalcone 2a (2.0 g, 0.0086957 mol), anhydrous
K2CO3 (2.0g), 1,3-dibromopropane (0.8782 g, 0.00434783 mol),
tetrabutyl ammonium iodide (1.0 g) in dry acetone (25.0mL) was
refluxed for 6 h with continuous stirring. The progress of reaction
was monitored by TLC. After the completion of reaction, the
reaction mixture turned to a colorless mass that was poured over
iced HCl to obtain a solid. The crude product thus obtained was
recrystallized from MeOH to yield pure compound 3a.
The observed minimum inhibitory concentration (MIC–m
g/ml) values of the studied compounds (3a–3g and 4a–4g)
have been presented in Tables 1 and 2 (Figs 1 and 2). Most
of the compounds showed significant activity against tested
microorganisms, and the compounds 3c–3g and 4c–4g
showed better MIC against the aforementioned microorgan-
isms at concentration of 12.5 mg/mL (Tables 1 and 2).
Journal of Heterocyclic Chemistry
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Synthesis of New Bis[4,5-dihydro-1-phenyl-5-thienyl-3-(phenyl-4-alkoxy)-
1H-pyrazole]derivatives
1165
Scheme 2
O
CH2 ( CH2)n
}
path a
OH
NH
(CH )
}
OCH
2 n
2
H+
S
S
O
b
HN
Ph
a
..
H N
NH
Ar
2
3a-3g
-H2O
+
path b
H
}
OCH
(CH )
2
2 n
S
..
O
CH2
( CH2)n
}
HN
Ph
N
3a'-3g'
S
OH
HN
..
+
cyclization
H
NH
Ph
H
3a''-3g''
OCH
(CH )
}
2
H
2 n
N
N
H
S
ketonization
Ph
}
( CH2)n
O
CH2
4a-4g
S
HN
O
..
HN
Ph
cyclization
H
}
O
CH2
( CH2)n
S
H
OH
N
N
H
Ph
-
H2O
O
CH2
( CH2)n
}
S
H
N
H
N
Ph
5a
-5g
3a: brown solid; yield 60%; mp: 110–112ꢁC. IR (KBr) cmꢀ1
1660 (C═O), 1596 (C═C), 2923 and 2870 (methylene C–H),
(C-20,60), 130.25 (C-500), 129.32 (C-300), 128.20 (C-400), 120.10 (C-2),
114.10 (C-30,50), 67.28 (OCH2CH2), 25.20 (OCH2CH2); MS
(ESI): m/z (M+ 1)+ 501. Anal. Calcd for C29O4H24S2: C, 69.6%;
H, 4.80%; S, 12.8%; found: C, 69.87%; H, 4.81%; S, 12.85%.
Synthesis of (2E,20E)-1,10-(4,40-(butane-1,4-diylbis(oxy))bis
1
1236 and 1034 (C–O); H NMR (400 MHz, CDCl3): d 8.00 (4H,
d, Jo =8.5 Hz, H-20, 60), 7.84 (2H, d, Jtrans = 14.5 H0z0, H-3), 7.51
00
00 00
(2H, d, J5 ,4 = 4.9Hz, H-5 ), 7.43 (4H, m, H-2, 3 ), 7.13 (2H,
t, J4“,5” = 4.9 Hz, H-400), 7.03 (4H, d, Jo = 8.6 Hz, H-30, 50), 4.29
(4H, t, Jvic = 5.8 Hz, OCH2CH2), 2.08 (2H, t, Jvic = 5.8Hz,
OCH2CH2); 13C NMR (100MHz, CDCl3): d 186.60 (C-1),
162.48 (C-40), 139.80 (C-3), 135.73 (C-200), 131.94 (C-10), 130.48
(4,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one 3b.
The
compound 3b was obtained by reacting 2a (2.0 g, 0.0086957 mol)
with 1,4-dibromobutane (0.9391 g, 0.00434783 mol) under similar
conditions as described for 3a.
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M. Yusuf and P. Jain
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July 2014
Synthesis of New Bis[4,5-dihydro-1-phenyl-5-thienyl-3-(phenyl-4-alkoxy)-
1H-pyrazole]derivatives
1167
In vitro MIC of bishalcones 3a-3g
E.coli
120
K.pneumoniae
100
P.aeruginosa
80
P.fluorescens
S.aureus
B.subtilis
S.pyrogens
60
40
20
0
A.janus
3f
3c
3a
3b
3d
3e
3g
P.glabrum
Amoxicillin
Fluconazole
A. niger
F.oxysporum
A.sclerotiorum
Name of Compounds
Figure 1. MIC (mg/mL) of bischalcones 3a–3g.
In vitro MIC of bispyrazolines 4a-4g
E.coli
60
50
40
30
20
10
0
K.pneumoniae
P.aeruginosa
P.fluorescens
S.aureus
B.subtilis
S.pyrogens
A.janus
g
4
e
4f
4c
lin
il
4a
4b
4d
4e
ol
ic
x
naz
o
o
P.glabrum
A.niger
c
Am
lu
F
F.oxysporum
A.sclerotiorum
Name of Compounds
Figure 2. MIC (mg/mL) of bispyrazolines 4a–4g.
Hz, H-20,60), 7.84 (2H, d, Jtrans = 15.3 Hz, H0-03), 7.56 (2H, d, J5 ,4 =5.0
3b: brown solid; yield 70%; mp: 172–174ꢁC. IR (KBr) cmꢀ1
1652 (C═O), 1595 (C═C), 2939 and 2874 (methylene C–H),
1238 and 1021 (C–O); 1H NMR (400MHz, CDCl3): d 8.02
(4H, d, Jo =8.8Hz, H-20, 60), 7.83 (2H, d, Jtrans = 15.2 Hz, H-3), 7.61
00 00
Hz, H-500), 7.48 (2H, d, J3 ,4 =3.6Hz, H-3 ), 7.44 (2H, d, Jtrans = 15.3
00 00
Hz, H-2), 7.13 (2H, dd, J= 3.6, 5.0 Hz, H-400), 7.00 (4H, d, Jo =8.2Hz,
H-30,50), 4.11 (4H, t, Jvic = 6.2 Hz, OCH2CH2CH2), 1.92
(4H, quintet, Jvic = 6.2 Hz, OCH2CH2CH2), 1.64 (2H, quintet,
Jvic = 6.2 Hz, CH2CH2CH2); 13C NMR (100 MHz, CDCl3):
d 186.68 (C-1), 162.47 (C-40), 139.80 (C-3), 135.63 (C-200),
131.95 (C-10), 130.49 (C-20,60), 130.24 (C-500), 129.29 (C-300),
128.22 (C-400), 120.15 (C-2), 114.12 (C-30,50), 67.39
(OCH2CH2CH2), 25.28 (OCH2CH2CH2), 25.19 (CH2CH2CH2);
MS(ESI): m/z (M+ Na)+ 551. Anal. Calcd for C31O4H28S2:
C, 70.45%; H, 5.30%; S, 12.12%; found: C, 70.17%; H, 5.28%;
S, 12.16%.
00
00
00 00
00 00
(2H, d, J5 ,4 =5.0Hz, H-5 ), 7.52 (2H, d, J3 ,4 =3.5Hz, H-3 ), 7.45
(2H, d, Jtrans = 15.2 Hz, H-2), 7.11 (2H, dd, J= 3.7, 5.0 Hz, H-400),
7.01 (4H, d, Jo =8.8Hz, H-30, 50), 4.14 (4H, t, Jvic =5.8Hz,
OCH2CH2), 1.96 (4H, quintet, Jvic =5.8Hz, OCH2CH2); 13C NMR
(100 MHz, CDCl3): d 186.65 (C-1), 162.45 (C-40), 139.84 (C-3),
135.69 (C-200), 131.90 (C-10), 130.46 (C-20, 60), 130.21 (C-500),
129.27 (C-300), 128.28 (C-400), 120.13 (C-2), 114.17 (C-30, 50), 67.37
(OCH2CH2), 25.26 (OCH2CH2); MS (ESI): m/z (M + 1)+ 515. Anal.
Calcd for C30O4H26S2: C, 70.03%; H, 5.05%; S, 12.45%; found:
C, 70.31%; H, 5.03%; S, 12.49%.
Synthesis of (2E,20E)-1,10-(4,40-(hexane-1,6-diylbis(oxy))bis
(4,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one 3d.
Synthesis of (2E,20E)-1,10-(4,40-(pentane-1,5-diylbis(oxy))bis(4,1-
The
compound 3d was prepared by reacting 2a (2.0 g, 0.0086957 mol)
with 1,6-dibromohexane (1.06086 g, 0.00434783 mol) under similar
conditions as described for 3a.
phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one
3c.
The
compound 3c was synthesized by treating 2a (2.0 g, 0.0086957 mol)
with 1,5-dibromopentane (0.9999 g, 0.00434783 mol) under similar
conditions as used for 3a.
3d: brown solid; yield 72%; mp: 197–199ꢁC, IR (KBr) cmꢀ1 1657
3c: brown solid; yield 68%; mp: 155–157ꢁC. IR (KBr) cmꢀ1 1656
(C═O), 1598, (C═C), 2932 and 2869 (methylene C–H), 1239
and 1027 (C–O); 1H NMR (400 MHz, CDCl3): d 8.01 (4H, d, Jo =8.2
(C═O), 1602 (C═C), 2930 and 2852 (methylene C–H), 1237 and 1028
(C–O); 1H NMR (400 MHz, CDCl3): d 8.01 (4H, d, Jo=8.8Hz,
0
H-20,6 ), 7.93 (2H, d, Jtrans = 15.2 Hz, H-3), 7.40 (2H, d, J5”,4” =5.0Hz,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

1168
M. Yusuf and P. Jain
Vol 51
(2H, d, J5”,4” =5.0Hz, H-500), 7.36 (2H, d, Jtrans = 15.3 Hz, H-2),
00
00
00 00
H-5 ), 7.35 (2H, d, J3 ,4 =3.5Hz, H-3 ), 7.32 (2H, d, Jtrans = 15.2 Hz, H-
2), 7.08 (2H, dd, J= 3.5, 5.0 Hz, H-400), 6.97 (4H, d, Jo =8.8Hz, H-30, 50),
4.06 (4H, t, Jvic =6.4Hz, OCH2CH2CH2), 1.87 (4H, quintet, Jvic =6.4Hz,
OCH2CH2CH2), 1.58 (4H, quintet, Jvic =6.4Hz, CH2CH2CH2); 13C
NMR (100 MHz, CDCl3): d 186.69 (C-1), 162.26 (C-40), 140.68 (C-3),
136.47 (C-200), 131.86 (C-10), 130.23 (C-500), 130.39 (C-20,60),
128.51 (C-300), 128.38 (C-400), 120.27 (C-2), 114.37 (C-30,50), 67.83
(OCH2CH2CH2), 29.13 (OCH2CH2CH2), 25.90 (CH2CH2CH2); MS
(ESI): m/z (M + Na)+ 565. Anal. Calcd for C32O4H30S2: C, 70.84%;
00
00 00
7.33 (2H, d, J3 ,4 =3.7Hz, H-3 ), 7.08 (2H, dd, J=3.7, 5.1Hz,
H-400), 6.96 (4H, d, Jo =8.8Hz, H-30,50), 4.03 (4H, t, Jvic =6.5Hz,
OCH2CH2CH2CH2CH2CH2), 1.81 (4H, quintet, Jvic = 6.5 Hz,
OCH2CH2CH2CH2CH2CH2), 1.47 (4H, quintet, Jvic = 5.6 Hz,
CH2CH2CH2CH2CH2CH2), 1.33 (12H, m, OCH2CH2CH2CH2CH2CH2 );
13C NMR (100 MHz,00 CDCl3): d 186.86 (C-1), 162.44 (C-40),
0
0
0
00
139.78 (C-3), 135.57 (C-2 ), 131.61 (C-1 ), 130.22 (C-2 ,6 ), 130.19 (C-5 ),
00
00
0 0
128.79 (C-3 ), 128.29 (C-4 ), 120.33 (C-2), 113.66 (C-3 ,5 ), 67.78
(OCH2CH2CH2CH2CH2CH2), 29.64 (OCH2CH2CH2CH2CH2CH2), 28.82
(OCH2CH2CH2CH2CH2CH2), 25.39 (OCH2CH2CH2CH2CH2CH2), 25.19
(OCH2CH2CH2CH2CH2CH2), 25.00 (OCH2CH2CH2CH2CH2CH2); MS
(ESI): m/z (M + Na)+ 649. Anal. Calcd for C38O4S2H42: C, 72.84%; H,
6.70%; S, 10.22%; found: C, 73.13%; H, 6.72%; S, 10.26%.
H, 5.53%; S, 11.80; found: C, 71.12%; H, 5.51%; S, 11.76%.
Synthesis of (2E,20E)-1,10-(4,40-(octane-1,8-diylbis(oxy))bis
(4,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one 3e.
The
compound 3e was obtained from the reaction of 2a (2.0 g,
0.0086957 mol) with 1,8-dibromooctane (1.18260 g, 0.00434783)
under similar conditions as used for 3a.
Synthesis of 1,3-bis[3-(4-phenyl)-4,5-dihydro-1-phenyl-5-
(thiophen-2-yl)-1H-pyrazole]propane 4a.
A mixture of 3a
3e: yellow solid; yield 78%; mp: 140–142ꢁC, IR (KBr) cmꢀ1
1658 (C═O), 1597 (C═C), 2940 and 2858 (methylene C–H),
1239 and 1020 (C–O); 1H NMR (400 MHz, CDCl3): d 7.99
(4H, d, Jo = 8.6 Hz, H-20, 60), 7.91 (2H, d, Jtrans = 14.9 Hz, H-3),
7.52 (2H, d, J5”,4” = 4.5 Hz, H-500), 7.45 (4H, m, H-2, 300), 7.12
(2H, d, J4”,5” = 4.5 Hz, H-400), 6.98 (4H, d, J = 8.6 Hz, H-30, 50),
4.02 (4H, t, Jvic = 6.6 Hz, OCH2CH2CH2CH2), 1.81 (4H, quintet,
Jvic =6.6Hz, OCH2CH2CH2CH2), 1.42 (8H, m, CH2CH2CH2CH2);
13C NMR (100 MHz, CDCl3): d 186.60 (C-1), 162.56 (C-40), 139.82
(C-3), 135.64 (C-200), 131.49 (C-10), 130.24 (C-20,60), 130.05 (C-500),
128.63 (C-300), 128.05 (C-400), 120.05 (C-2), 113.96 (C-30,50),
67.70 (OCH2CH2CH2CH2), 28.65 (OCH2CH2CH2CH2), 28.49
(OCH2CH2CH2CH2), 25.34 (OCH2CH2CH2CH2); MS (ESI): m/z
(M)+ 570. Anal. Calcd for C34O4H34S2: C, 71.57%; H, 5.96%; S,
11.22%; found: C, 71.85%; H, 5.94%; S, 11.26%.
(1.0 g, 0.001929 mol) and phenyl hydrazine (0.4183 g, 0.0038839 mol)
in dry EtOH (30 mL) was refluxed for 8 h. The progress of reaction
was monitored by TLC. The resulting reaction mixture was
concentrated in vacuo to obtain a solid compound, which was further
crystallized from CH3OH to yield pure compound 4a.
4a: brown solid; yield 62%; mp: 99–101ꢁC, IR (KBr) cmꢀ1 1593
(C═N), 2945 and 2840 (methylene C–H), 1242 and 1025 (C–O);
1H NMR (400MHz, CDCl3): d 7.63 (4H, d, Jo = 8.6Hz, H-2000,6000),
00
00 00
00 00
7.33 (2H, d, J3 ,4 = 3.7 Hz, H-3 ), 7.22 (2H, d, J5 ,4 = 5.0 Hz, H-
500), 7.12 (6H, m, H-30,40, 50), 6.99 (4H, d, Jo = 8.6 Hz, H-3000,5000),
6.89 (2H, dd, J = 3.7, 5.0 Hz, H-400), 6.70 (4H, t, J = 7.2 Hz, H-20,
60), 5.60 (2H, dd, JXA = 6.2 Hz, JXM = 11.8Hz, HX), 4.02 (4H, t,
Jvic = 5.8Hz, OCH2CH2), 3.82 (2H, dd, J = 11.8, 17.2 Hz, HM),
3.19 (2H, dd, JAX = 6.2 Hz, JAM = 17.2 Hz, HA), 2.50 (4H, quin-
tet, Jvic = 5.8 Hz, OCH2CH2); 13C NMR (100 MHz, CDCl3): d
160.15 (C-4000), 154.26 (C-3), 145.15 (C-10), 147.34 (C-200),
144.87 (C-1000), 128.03 (C-500), 127.55 (C-300), 126.26 (C-400),
126.30 (C-2000, 6000), 124.68 (C-30, 50), 118.60 (C-40), 114.90
(C-3000,5000), 113.77 (C-20, 60), 67.10 (OCH2CH2), 59.41 (C-5),
43.39 (C-4), 24.47 (OCH2CH2); MS (ESI): m/z (M + Na)+
671. Anal. Calcd for C41O2N4H36S2: C, 72.35%; H, 5.29%;
N, 8.23%; S, 9.41%; found: C, 72.63%; H, 5.27%; N, 8.23%;
S, 9.41%.
Synthesis of (2E,20E)-1,10-(4,40-(decane-1,10-diylbis(oxy))bis
(4,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-one 3f.
The
bischalcone 3f was synthesized by reacting 2a (2.0 g, 0.0086957 mol)
with 1,10-dibromodecane (1.3046 g, 0.00434783 mol) under similar
conditions as described for 3a.
3f: brown solid; yield 75%; mp: 118–120ꢁC, IR (KBr) cmꢀ1
1661 (C═O), 1594 (C═C), 2938 and 2878 (methylene C–H),
1
1245 and 1028 (C–O); H NMR (400 MHz, CDCl3): d 8.00 (4H,
d, Jo = 8.4Hz, H-20, 60), 7.94 (4H, m, H-3, 500), 7.53 (2H, d, J3 ,4
=
00 00
Synthesis of 1,4-bis[3-(4-phenyl)-4,5-dihydro-1-phenyl-5-
3.8 Hz, H-300), 7.43 (2H, d, Jtrans = 15.0 Hz, H-2), 7.12 (2H, d,
J4”,3” = 3.8Hz, H-400), 6.98 (4H, d, Jo = 8.4 Hz, H-30,50), 4.00 (4H,
t, Jvic =6.1Hz, OCH2CH2CH2CH2CH2), 1.78 (4H, quintet, Jvic =6.1
Hz, OCH2CH2CH2CH2CH2), 1.35 (12H, m, CH2CH2CH2CH2CH2);
13C NMR (100 MHz, CDCl3): d 186.66 (C-1), 162.50 (C-40), 139.80
(C-3), 135.67 (C-200), 131.50 (C-10), 130.26 (C-20,60), 130.15 (C-500),
128.69 (C-300), 128.09 (C-400), 120.23 (C-2), 113.99 (C-30,50), 67.56
(OCH2CH2CH2CH2CH2), 28.60 (OCH2CH2CH2CH2CH2), 28.52
(OCH2CH2CH2CH2CH2), 25.30 (OCH2CH2CH2CH2CH2), 25.12
(OCH2CH2CH2CH2CH2); MS (ESI): m/z (M + H)+ 599. Anal. Calcd
for C36O4H38S2: C, 72.24%; H, 6.35%; S; 10.70%; found: C,
71.96%; H, 6.33%; S, 10.74%.
(thiophen-2-yl)-1H-pyrazole]butane 4b.
The compound 4b
was synthesized from the reaction of bischalcone 3b (1.0 g,
0.00195 mol) with phenyl hydrazine (0.4212 g, 0.0039 mol)
under similar conditions as described earlier for 4a.
4b: yellow solid; yield 68%; mp: 145–147ꢁC, IR (KBr) cmꢀ1
1597 (C═N), 2925 and 2871 (methylene C–H), 1238 and 1019
1
(C–O); H NMR (400 MHz, CDCl3): d 7.67 (4H, d, Jo = 8.6 Hz,
H-2000,6000), 7.30 (2H, d, J3 ,4 = 3.7 Hz, H-3 ), 7.17 (2H, d, J5 ,4
=
00
00 00
00 00
5.0 Hz, H-500), 7.09 (6H, m, H-30,40, 50), 6.95 (4H, d, Jo = 8.6 Hz,
H-3000,5000), 6.92 (2H, dd, J = 3.7, 5.0 Hz, H-400), 6.73 (4H, t,
J = 7.2 Hz, H-20, 60), 5.67 (2H, dd, JXA = 6.2 Hz, JXM = 11.8 Hz,
HX), 4.09 (4H, brs, OCH2CH2), 3.86 (2H, dd, J = 11.8, 17.2 Hz,
HM), 3.21 (2H, dd, JAX = 6.2 Hz, JAM = 17.2 Hz, HA), 2.52
(4H, brs, OCH2CH2); 13C NMR (100 MHz, CDCl3): d 160.12
(C-4000), 155.56 (C-3), 147.50 (C-200), 145.85 (C-10), 144.77 (C-
1000), 128.53 (C-500), 127.15 (C-300), 126.78 (C-2000, 6000), 126.66
(C-400), 124.48 (C-30, 50), 118.70 (C-40), 114.40 (C-3000,5000),
113.27 (C-20, 60), 67.13 (OCH2CH2), 59.47 (C-5), 43.41 (C-4),
25.37 (OCH2CH2); MS (ESI): m/z (M+ Na)+ 685. Anal. Calcd for
C42O2N4H38S2: C, 72.62%; H, 5.47%; N, 8.07%; S, 9.22%; found:
C, 72.91%; H, 5.49%; N, 8.10%; S, 9.25%.
Synthesis of (2E,20E)-1,10-(4,40-(dodecane-1,12-diylbis
(oxy))bis(4,1-phenylene))bis(3-(thiophen-2-yl)prop-2-en-1-
one 3g.
The bischalcone 3g was prepared by treating 2a
(2.0 g, 0.0086957 mol) with 1,12-dibromododecane (1.4260 g,
0.004347 mol) under similar conditions as used for 3a.
3g: brown solid; yield 80%; mp: 130–132ꢁC, IR (KBr) cmꢀ1 1654
(C═O), 1595 (C═C), 2920 and 2855 (methylene C–H), 1238
1
and 1022 (C–O); H NMR (400 MHz, CDCl3): d 8.00 (4H, d,
Jo = 8.8 Hz, H-20, 60), 7.93 (2H, d, Jtrans = 15.3 Hz, H-3), 7.40
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

July 2014
Synthesis of New Bis[4,5-dihydro-1-phenyl-5-thienyl-3-(phenyl-4-alkoxy)-
1H-pyrazole]derivatives
1169
Hz, OCH2CH2CH2CH2), 1.41 (4H, m, OCH2CH2CH2CH2); 13C
NMR (100 MHz, CDCl3): d 160.50 (C-4000), 155.78 (C-3), 147.71
(C-200), 145.90 (C-10), 144.80 (C-1000), 128.56 (C-500), 127.11
(C-300), 126.60 (C-400), 126.48 (C-2000, 6000), 124.59 (C-30,50),
118.99 (C-40), 114.69 (C-3000,5000), 113.50 (C-20, 60), 67.45
(OCH2CH2CH2CH2), 59.74 (C-5), 43.62 (C-4), 28.49
(OCH2CH2CH2CH2), 25.79 (OCH2CH2CH2CH2), 25.19
(OCH2CH2CH2CH2); MS (ESI): m/z (M)+ 718. Anal. Calcd for
C46O2N4H46S2: C, 73.60%; H, 6.13%; N, 7.46%; S, 8.53%; found:
C, 73.89%; H, 6.15%; N, 7.43%; S, 8.49%.
Synthesis of 1,5-bis[3-(4-phenyl)-4,5-dihydro-1-phenyl-5-
(thiophen-2-yl)-1H-pyrazole]pentane 4c. The compound 4c
was prepared from the reaction of bischalcone 3c (1.0 g,
0.00189 mol) with phenyl hydrazine (0.40824 g, 0.00378 mol)
under similar conditions as described earlier for 4a.
4c: brown solid; yield 65%; mp: 125–127ꢁC, IR (KBr) cmꢀ1
1592 (C═N), 2930 and 2869 (methylene C–H), 1234 and 1026
1
(C–O); H NMR (400 MHz, CDCl3): d 7.68 (4H, d, Jp,o =8.6Hz,
00
H-2000,6000), 7.32 (2H, d, J3 ,4 =3.7Hz, H-3 ), 7.19 (2H, d, J5 ,4
=
00 00
00
0
5.0 Hz, H-500), 7.02 (6H, m, H-30,40,50), 6.92 (4H, d,
Jo =8.6Hz, H-3000,5000), 6.90 (2H, dd, J= 3.7, 5.0 Hz, H-400), 6.79
(4H, t, J=7.2Hz, H-20,60), 5.62 (2H, dd, JXA =6.2Hz, JXM =11.8
Hz, HX), 4.03 (4H, t, Jvic =6.0Hz, OCH2CH2CH2), 3.81 (2H, dd,
Synthesis of 1,10-bis[3-(4-phenyl)-4,5-dihydro-1-phenyl-5-
(thiophen-2-yl)-1H-pyrazole]decane 4f.
The compound 4c
was obtained from the reaction of bischalcone 3f (1.0 g,
0.00167 mol) with phenyl hydrazine (0.3607 g, 0.00334 mol)
under similar conditions as used earlier for 4a.
J= 11.8 Hz, JMA = 17.2 Hz, HM), 3.24 (2H, dd, JAX =6.2Hz, JAM
=
17.2 Hz, HA), 2.32 (4H, quintet, Jvic =6.0Hz, OCH2CH2CH2),
1.58 (2H, m, OCH2CH2CH2); 13C NMR (100 MHz, CDCl3): d
160.19 (C-4000), 155.50 (C-3), 147.67 (C-200), 145.80 (C-10), 144.70
(C-1000), 128.59 (C-500), 127.19 (C-300), 126.67 (C-2000, 6000), 126.60
(C-400), 124.03 (C-30,50), 118.79 (C-40), 114.48 (C-3000,5000), 113.45
(C-20, 60), 67.10 (OCH2CH2CH2), 59.49 (C-5), 43.47 (C-4), 28.39
(OCH2CH2CH2), 25.67 (OCH2CH2CH2); MS (ESI): m/z (M + H)+
677. Anal. Calcd for C43O2N4H40S2: C, 72.88%; H, 5.64%; N,
7.90%; S, 9.03%; found: C, 72.59%; H, 5.62%; N, 7.93%; S, 9.06%.
Synthesis of 1,6-bis[3-(4-phenyl)-4,5-dihydro-1-phenyl-5-
4f: yellow solid; yield 60%; mp: 126–128ꢁC, IR (KBr) cmꢀ1
1593 (C═N), 2929 and 2857 (methylene C–H), 1230 and 1021
1
(C–O); H NMR (400 MHz, CDCl3): d 7.64 (40H0 , d, Jo = 8.7 Hz,
H-2000, 6000), 7.34 (2H, d, J3 ,4 = 3.6 Hz, H-3 ), 7.19 (2H, d,
00 00
J5”,4” = 5.2 Hz, H-500), 7.10 (6H, m, H-30, 40, 50), 6.94 (2H, dd,
J = 3.6, 5.2 Hz, H-400), 6.92 (4H, d, Jo = 8.7 Hz, H-3000,5000), 6.75
(4H, t, J = 7.0 Hz, H-20, 60), 5.56 (2H, dd, JXA = 6.9Hz, JXM = 11.5
Hz, HX), 3.98 (4H, t, Jvic = 6.3 Hz, OCH2CH2CH2CH2CH2), 3.82
(2H, dd, JMX = 11.8 Hz, JMA =17.0 Hz, HM), 3.20 (2H, dd, JAX
=
(thiophen-2-yl)-1H-pyrazole]hexane 4d.
The compound 4c
6.9 Hz, JAM = 17.0Hz, HA), 1.79 (4H, quintet, Jvic = 6.3Hz,
OCH2CH2CH2CH2CH2), 1.46 (4H, quintet, Jvic = 6.3Hz,
OCH2CH2CH2CH2CH2), 1.35 (8H, m, OCH2CH2CH2CH2CH2);
13C NMR (100 MHz, CDCl3): d 159.35 (C-4000), 156.23 (C-3),
145.79 (C-10), 145.62 (C-200), 144.88 (C-1000), 128.38 (C-500),
126.90 (C-300), 126.43 (C-400), 125.97 (C-2000, 6000), 124.46 (C-
30,50), 118.74 (C-40), 114.15 (C-20, 60), 113.19 (C-3000,5000), 67.47
(OCH2CH2CH2CH2CH2), 59.73 (C-5), 43.54 (C-4), 28.84
(OCH2CH2CH2CH2CH2), 28.72 (OCH2CH2CH2CH2CH2), 28.61
(OCH2CH2CH2CH2CH2), 25.42 (OCH2CH2CH2CH2CH2); MS (ESI): m/
z (M + 1)+ 747. Anal. Calcd for C48O2N4H50S2: C, 74.03%; H, 6.42%; N,
7.20%; S, 8.22%; found: C, 74.32%; H, 6.39%; N, 7.22%; S, 8.25%.
Synthesis of 1,12-bis[3-(4-phenyl)-4,5-dihydro-1-phenyl-5-
(thiophen-2-yl)-1H-pyrazole]dodecane 4g. The compound 4c
was synthesized from the reaction of bischalcone 3g (1.0 g,
0.0016 mol) with phenyl hydrazine (0.3456 g, 0.0032mol) under
similar conditions as described earlier for 4a.
was obtained by treating bischalcone 3d (1.0 g, 0.00185 mol) with
phenyl hydrazine (0.3996g, 0.00370 mol) under similar conditions
as described earlier for 4a.
4d: yellow solid; yield 61%; mp: 166–168ꢁC, IR (KBr) cmꢀ1 1599
(C═N), 2937 and 2876 (methylene C–H), 1240 and 1018 (C–O);
1H NMR (400 MHz, CDCl3): d 7.66 (4H, d, Jo =8.8Hz, H-2000,600000),
00
00 00
00 00
7.40 (2H, d, J3 ,4 =3.8Hz, H-3 ), 7.24 (2H, d, J5 ,4 =5.2Hz, H-5 ),
7.10 (6H, m, H-30, 40, 50), 6.93 (2H, dd, J=3.8, 5.2Hz, H-400), 6.88
(2H, d, Jo =8.8Hz, H-3000, 5000), 6.73 (4H, t, J=8.7Hz, H-20, 60), 5.59
(2H, dd, JXA =6.7Hz, JXM = 12.2 Hz, HX), 4.00 (4H, t,
Jvic =6.0Hz, OCH2CH2CH2), 3.85 (2H, dd, JMX = 12.2 Hz, JMA
=
17.4 Hz, HM), 3.23 (2H, dd, JAX =6.6Hz, JAM = 17.4 Hz, HA), 1.56
(4H, quintet, Jvic =6.0Hz, OCH2CH2CH2), 1.51 (4H, quintet, Jvic =6.0
Hz, OCH2CH2CH2); 13C NMR (100 MHz, CDCl3): d 160.39 (C-4000),
155.58 (C-3), 147.73 (C-200), 145.95 (C-10), 144.86 (C-1000), 128.78
(C-500), 127.14 (C-300), 126.69 (C-400), 126.43 (C-2000, 6000), 124.60
(C-30, 50), 118.91 (C-40), 114.62 (C-3000,5000), 113.48 (C-20, 60), 67.23
(OCH2CH2CH2), 59.59 (C-5), 43.50 (C-4), 28.43 (OCH2CH2CH2),
25.70 (OCH2CH2CH2); MS (ESI): m/z (M + Na)+ 713. Anal. Calcd
for C44O2N4H42S2: C, 73.13%; H, 5.82%; N, 7.76%; S, 8.86%; found:
C, 72.83%; H, 5.84%; N, 7.73%; S, 8.89%.
4g: orange solid; yield 63%; mp: 110–112ꢁC, IR (KBr) cmꢀ1 1596
(C═N), 2923 and 2875 (methylene C–H), 1238 and 1029 (C–O); 1H
NMR (400 MHz, CDCl3): d 7.66 (4H, d, Jo =8.8Hz, H-2000,6000), 7.0204
(2H, dd, J= 3.7, 0.8 Hz, H-300), 7.16 (2H, d, J5 ,4 =5.2Hz, H-5 ),
00 00
7.04 (6H, m, H-30,40, 50), 6.98 (4H, d, Jo =8.8Hz, H-3000, 5000), 6.90
(2H, dd, J= 3.7, 5.5 Hz, H-400), 6.74 (4H, t, J=7.2Hz, H-20, 60),
5.60 (2H, dd, JXA =6.6Hz, JXM = 11.8 Hz, HX), 3.98 (4H, t, Jvic =6.4
Hz, OCH2CH2CH2CH2CH2CH2), 3.84 (2H, dd, JMX = 11.8 Hz,
JMA = 17.2 Hz, HM), 3.21 (2H, dd, JAX =6.6Hz, JAM = 17.2 Hz, HA),
1.78 (4H, quintet, Jvic =6.4Hz, OCH2CH2CH2CH2CH2CH2), 1.45
(4H, quintet, Jvic = 6.4 Hz, OCH2CH2CH2CH2CH2CH2), 1.30
(12H, m, OCH2CH2CH2CH2CH2CH2); 13C NMR (100 MHz,
CDCl3): d 160.45 (C-4000), 155.42 (C-3), 145.53 (C-200), 145.78
Synthesis of 1,8-bis[3-(4-phenyl)-4,5-dihydro-1-phenyl-5-
(thiophen-2-yl)-1H-pyrazole]octane 4e.
The compound 4c
was prepared from the reaction of bischalcone 3e (1.0 g,
0.00175mol) with phenyl hydrazine (0.378g, 0.0035 mol) under
similar conditions as used earlier for 4a.
4e: yellow solid; yield 70%; mp: 152–154ꢁC, IR (KBr) cmꢀ1 1595
(C═N), 2920 and 2858 (methylene C–H), 1241 and 1034 (C–O); 1H
NMR (400 MHz, CDCl3): d 7.60 (4H, d, Jo =8.2Hz, H-2000,600000),
00
000
(C-10), 144.79 (C-1 ), 128.43 (C-500), 126.98 (C-300), 126.58 (C-
00 00
00 00
7.38 (2H, d, J3 ,4 =3.8Hz, H-3 ), 7.23 (2H, d, J5 ,4 =4.9Hz, H-5 ),
7.10 (6H, m, H-30,40, 50), 6.92 (2H, dd, J= 3.8, 4.9 Hz, H-400), 6.86
(4H, d, Jo =8.2Hz, H-3000,5000), 6.74 (4H, t, J=7.0Hz, H-20, 60), 5.58
(2H, dd, JXA =6.8Hz, JXM = 12.2 Hz, HX), 3.99 (4H, t, Jvic =6.1Hz,
OCH2CH2CH2CH2), 3.83 (2H, dd, JMX = 12.2 Hz, JMA =16.5Hz,
HM), 3.22 (2H, dd, JAX =6.8Hz, JAM =16.5Hz, HA), 1.78 (4H,
quintet, Jvic =6.1Hz, OCH2CH2CH2CH2), 1.48 (4H, quintet, Jvic =6.1
000
000
0
0
0
0
400), 124.61 (C-2 , 0600 ), 124.16 (C-3 , 5 ), 118.70 (C-4 ), 114.22 (C-2 ,
0
000
6 ), 113.21 (C-3 ,5 ), 67.38 (OCH2CH2CH2CH2CH2CH2), 59.62 (C-
5), 43.25 (C-4), 28.94 (OCH2CH2CH2 CH2CH2CH2), 28.77
(OCH2CH2CH2CH2CH2CH2), 28.42 (OCH2CH2CH2CH2CH2CH2),
28.02 (OCH2CH2CH2CH2CH2CH2), 25.45 (OCH2CH2CH2CH2CH2CH2);
MS (ESI): m/z (M + Na)+ 797. Anal. Calcd for C50O2N4H54S2:
Journal of Heterocyclic Chemistry
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M. Yusuf and P. Jain
Vol 51
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C, 74.44%; H, 6.70%; N, 6.95%; S, 7.94%; found: C, 74.65%; H,
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Acknowledgment. Authors are highly thankful to Department of
Science and Technology (SERC, fast track scheme no. SR/FT/
CS-041/2010), New Delhi for providing the financial support
for this research work.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet