Synthesis of a new class of sulfonamido bis heterocycles - Pyrrolyl/pyrazolyl-1,3,4-oxadiazoles, 1,3,4-thiadiazoles, and 1,2,4-triazoles

Article abstract of DOI:10.1002/jhet.1679

A new class of sulfonamido bis heterocycles - pyrrolyl/pyrazolyl- oxadiazoles, thiadiazoles, and triazoles - were prepared from arylaminosulfonylacetic acid hydrazide and E-aroylethenesulfonylacetic acid adopting simple and versatile synthetic methodologies.

Full text of DOI:10.1002/jhet.1679

Month 2013
Synthesis of a New Class of Sulfonamido Bis Heterocycles—Pyrrolyl/
Pyrazolyl-1,3,4-oxadiazoles, 1,3,4-Thiadiazoles, and 1,2,4-Triazoles
Akkarapalli Muralikrishna, Guda Mallikarjuna Reddy, Gopala Lavanya, Venkatapuram Padmavathi, and
*
Adivireddy Padmaja
Department of Chemistry, Sri Venkateswara University, Tirupati 517 502, Andhra Pradesh, India
*
E-mail: adivireddyp@yahoo.co.in
Received September 6, 2011
DOI 10.1002/jhet.1679
Published online 00 Month 2013 in Wiley Online Library (wileyonlinelibrary.com).
R
O
O
N
N
O
O
O
O
O
O
S
S
S
S
S
N
H
X
H
H
N
N
6 / 7 / 8
S
NH2
OH
R
R
N
H
O
O
O
R
R
R
N
N
1
O
O
+
N
H
X
O
N
15 / 16 / 17
N
H
S
O
O
R
O
N
N
O
O
O
O
R
2
S
N
H
X
6, 15, 18 : X = O
7, 16, 19 : X = S
8, 17, 20 : X = N-NH2
N
N
H
18 / 19 / 20
A new class of sulfonamido bis heterocycles—pyrrolyl/pyrazolyl-oxadiazoles, thiadiazoles, and triazoles—
were prepared from arylaminosulfonylacetic acid hydrazide and E-aroylethenesulfonylacetic acid adopting
simple and versatile synthetic methodologies.
J. Heterocyclic Chem., 00, 00 (2013).
INTRODUCTION
of interest in pharmaceutical and agrochemical fields [7].
Substituted 1,3,4-thiadiazoles have become very useful
compounds in medicine and agriculture as herbicides [8],
fungicides [9], and bacteriocides [10]. Compounds bearing
1,2,4-triazole ring are used as powerful antimicrobial [11],
anticonvulsant [12], antidepressant [13], antihypertensive
[14], antitumorial [15], and analgesic [16] agents. Different
methods have been reported for the synthesis of 1,3,4-
oxadiazoles involving cyclization of diacylhydrazines pre-
pared from acyl chlorides and hydrazine in the presence of
dehydrating agents [17]. Replacement of –O– by –S– or –
NH– in some heterocycles was reported viz. Bordners [18]
preparation of pyrroles from furan and the transformation
of epoxides to episulfides by the action of thiocyanates or
thiourea [19–21]. However, reports about the conversion
of 1,3,4-oxadiazoles to 1,3,4-thiadiazoles and 1,2,4-triazoles
are relatively less [22,23]. Consequently, the development
of effective methods for the rapid and concise synthesis of
differently substituted bis heterocycles and modification of
oxadiazole motif is of considerable importance in organic
synthesis. Motivated by the aforesaid findings and pursuing
our studies on different five-membered heterocycles, we
herein designed to synthesize a new series of sulfonamido
bis heterocycles.
Various aryl-substituted aromatic heterocycles are known
to exhibit interesting biological activities and are also useful
as p-conjugated organic materials. Netrospin and distamycin
are pyrrole polyamides and are naturally occurring antican-
cer antibiotics [1]. 3,4-Disubstituted pyrroles were reported
either by coupling imines and nitroalkanes or by using
Friedel–Craft’s acylation in the presence of an electron-with-
drawing group on the pyrrole nitrogen or on 3,4-silylated
precursors [2]. The former compounds were also synthesized
from Michael acceptors and tosylmethyl isocyanide (TosMIC)
[3]. Following this synthetic methodology, we have reported
recently a new regioselective one-step procedure using phe-
nyl vinyl sulfone, aryl styryl sulfones, benzyl styryl sulfones,
and TosMIC, leading to a series of 3,4-disubstituted pyrroles
in good yields [4]. Another class of importance amongst
azole derivatives is pyrazole because of its chemotherapeutic
properties. Celecoxib, a pyrazole derivative is widely used in
the market as an anti-inflammatory drug [5]. In fact, the
popular methods for the synthesis of pyrazolines include
1,3-dipolar cycloaddition and [2 + 3] cyclocondensation
methodologies [6]. Besides, 1,3,4-oxadiazole is the most
significant heterocycle cores. 1,3,4-Oxadiazole derivatives
act as acid, ester, and amide bioisosteres and hence are
© 2013 HeteroCorporation

A. Muralikrishna, G. Mallikarjuna Reddy, G. Lavanya, V. Padmavathi, and A. Padmaja
Vol 000
RESULTS AND DISCUSSION
and 5 with TosMIC in the presence of NaH in a solvent
mixture of DMSO and ether produced 2-(arylaminosul-
fonylmethyl)-5-(30-aroyl-10H-pyrrol-40-ylsulfonyl-methyl)-
1,3,4-oxadiazole (6), 2-(arylaminosulfonylmethyl)-5-(30-aroyl-1
0H-pyrrol-40-ylsulfonyl-methyl)-1,3,4-thiadiazole (7), and
4-amino-3-(arylaminosulfonylmethyl)-5-(30-aroyl-10H-pyrrol-
40-ylsulfonylmethyl)-1,2,4-triazole (8) (Scheme 2 and Table 1).
The activated olefin, 2-(arylaminosulfonylmethyl)-5-
[E-(2-aroylvinylsulfonylmethyl)]-1,3,4-oxadiazole (3) was
synthesized by the condensation reaction of arylaminosul-
fonylacetic acid hydrazide (1) with E-aroylethenesulfony-
lacetic acid (2) in the presence of POCl3. Treatment of
compound 3 with thiourea in THF furnished 2-(arylamino-
sulfonylmethyl)-5-[E-(2-aroylvinylsulfonylmethyl)]-1,3,4-
thiadiazole (4). Similarly, interconversion of oxadiazole to
triazole was effected with hydrazine hydrate in n-butanol
to obtain 4-amino-3-(arylaminosulfonylmethyl)-5-E-(2-
aroylvinylsulfonylmethyl)-1,2,4-triazole (5) (Scheme 1 and
Table 1). In 1H NMR spectra, compounds 3a and 4a showed
two singlets at d 5.61, 5.02 and 5.42, 5.14 due to methylene
protons attached to C-2 and C-5 whereas 5a at 5.43 and
5.19ppm due to methylene protons attached to C-3 and C-
5. The downfield signal was attributed to the one adjacent
to sulfonamide moiety. Besides, a doublet was observed at
d 7.10 in 3a, at 6.87 in 4a, and at 6.81 ppm in 5a due to olefin
proton HB. However, the other olefin proton HA displayed a
doublet at downfield region and merged with aromatic
protons. The coupling constant value J ꢀ 14.1 Hz indicated
that they possess trans geometry. Apart from these, a broad
singlet was observed at d 10.32 in 3a, at 10.41 in 4a, and
at 10.37 ppm in 5a due to NH. Compound 5a displayed
another broad singlet at 5.75 ppm due to NH2. The signals
corresponding to NH and NH2 disappeared on deuteration
(Table 3).
1
In H NMR spectra, compounds 6a, 7a, and 8a displayed
two singlets at d 5.39, 5.34, 5.35 and 5.21, 5.12, 5.23 ppm
due to two methylene protons attached to C-2 and C-5 of
oxadiazole/thiadiazole and C-3 and C-5 of triazole units.
In addition, a singlet was observed at d 6.71, 6.83, and
0
6.79ppm due to C5 -H of pyrrole ring whereas the other
0
proton C2 -H displayed signal at downfield region and
merged with aromatic protons. Besides, two broad singlets
were appeared at d 8.82, 10.37 in 6a, at 8.46, 10.41 in 7a
and at 8.43, 10.46ppm in 8a due to NH of pyrrole ring
and NH–SO2. Compound 8a exhibited another broad singlet
at 5.58ppm due to NH2. The signals for NH and NH2
disappeared on deuteration. On the other hand, the 1,3-
dipolar cycloaddition of diazomethane to 3, 4, and 5 in
the presence of Et3N in ether at ꢁ20 to ꢁ15ꢂC afforded
2-(arylaminosulfonylmethyl)-5-(30-aroyl-40,50-dihydro-1
0H-pyrazol-40-ylsulfonylmethyl)-1,3,4-oxadiazole (9), 2-
(arylaminosulfonylmethyl)-5-(30-aroyl-40,50-dihydro-10
H-pyrazol-40-ylsulfonylmethyl)-1,3,4-thiadiazole (10), and 4-
amino-3-(arylaminosulfonylmethyl)-5-(30-aroyl-40,50-dihydro-10
H-pyrazol-40-ylsulfonylmethyl)-1,2,4-triazole (11) (Scheme 2
and Table 1). In 1H NMR spectra, compounds 9a, 10a, and
11a displayed an AMX splitting pattern for pyrazoline ring
protons in addition to two singlets due to methylene protons
The olefin moiety present in 3, 4, and 5 was utilized to
develop pyrrole and pyrazole rings. The reaction of 3, 4,
Scheme 1
O
H
H
N
OH
N
S
S
NH2
O
O
+
O
O
O
R
O
R
R
2
1
i
R
HB
N
N
4
3
O
O
O
O
2
5
S
1
O
3
S
N
H
HA
O
iii
ii
R
R
R
R
N
N
N
3
N
1
2
O
O
O
O
O
O
O
O
5
S
S
S
S
4
N
H
N
S
N
H
O
O
NH2
4
5
(i) POCl3
(ii) NH2CSNH2 / THF
(iii) NH2NH2.H2O / n-Butanol
R a) H
b) Me
c) Cl
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Synthesis of a New Class of Sulfonamido Bis Heterocycles
Table 1
Physical and analytical data of compounds 3–20.
Anal. Calcd/Found
Compound
3a
mp (ꢂC)
128–130
109–111
147–149
162–164
174–176
188–190
167–168
187–189
202–203
134–136
149–151
155–157
166–168
171–173
183–185
170–172
180–182
200–202
144–146
156–158
163–165
175–177
183–185
189–191
178–180
195–197
210–212
152–154
166–168
173–175
Yield (%)
69
66
70
72
67
74
68
71
75
73
70
74
69
67
72
75
71
75
73
68
70
66
69
75
77
72
76
66
65
68
Molecular formula (mol. wt)
C
H
N
C
19H17N3O6S2
(447.48)
51.00
51.06
53.04
53.08
44.19
44.25
49.23
49.26
51.31
51.36
42.86
42.82
49.45
49.48
51.52
51.58
43.02
43.05
51.84
51.89
53.68
53.64
45.41
45.43
50.19
50.24
52.06
52.03
44.14
44.20
50.39
50.43
52.26
52.29
44.29
44.26
49.07
49.13
51.05
51.01
43.02
43.07
47.51
47.54
49.52
49.58
41.81
41.76
47.70
47.73
49.70
49.66
41.96
42.00
49.45
49.41
51.52
51.55
43.02
3.83
3.81
4.45
4.48
2.93
2.94
3.70
3.73
4.31
4.34
2.84
2.82
4.15
4.12
4.74
4.76
3.23
3.27
3.73
3.76
4.31
4.30
2.90
2.91
3.61
3.62
4.18
4.21
2.82
2.80
4.03
4.06
4.58
4.56
3.19
3.22
3.91
3.92
4.48
4.52
3.07
3.06
3.79
3.82
4.34
4.38
2.98
2.99
4.20
4.23
4.74
4.72
3.35
3.36
4.15
4.16
4.74
4.77
3.23
9.39
9.47
8.84
8.90
8.14
8.19
9.06
9.11
8.55
3b
C21H21N3O6S2
(475.54)
C19H15Cl2N3O6S2
(516.37)
C19H17N3O5S3
(463.55)
C21H21N3O5S3
(491.60)
C19H15Cl2N3O5S3
(532.44)
C19H19N5O5S2
(461.51)
C21H23N5O5S2
(489.57)
C19H17Cl2N5O5S2
(530.40)
C21H18N4O6S2
(486.52)
C23H22N4O6S2
(514.57)
C21H16Cl2N4O6S2
(555.41)
C21H18N4O5S3
(502.59)
C23H22N4O5S3
(530.64)
C21H16Cl2N4O5S3
(571.48)
C21H20N6O5S2
(500.55)
C23H24N6O5S2
(528.60)
C21H18Cl2N6O5S2
(569.44)
C20H19N5O6S2
(489.52)
C22H23N5O6S2
(517.58)
C20H17Cl2N5O6S2
(558.41)
C20H19N5O5S3
(505.59)
C22H23N5O5S3
(533.64)
C20H17Cl2N5O5S3
(574.48)
C20H21N7O5S2
(503.55)
C22H25N7O5S2
(531.61)
C20H19Cl2N7O5S2
(572.44)
C19H19N5O5S2
(461.51)
C21H23N5O5S2
(489.57)
3c
4a
4b
8.59
7.89
7.85
4c
5a
15.17
15.25
14.31
14.36
13.20
13.27
11.52
11.56
10.89
10.84
10.09
10.16
11.15
11.23
10.56
10.61
9.80
5b
5c
6a
6b
6c
7a
7b
7c
9.86
8a
16.79
16.88
15.90
15.97
14.76
14.71
14.31
14.35
13.53
13.60
12.54
12.59
13.85
13.80
13.12
13.18
12.19
12.16
19.47
19.55
18.44
18.50
17.13
17.07
15.17
15.27
14.31
14.38
13.20
8b
8c
9a
9b
9c
10a
10b
10c
11a
11b
11c
12a
12b
12c
C19H17Cl2N5O5S2
(Continued)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. Muralikrishna, G. Mallikarjuna Reddy, G. Lavanya, V. Padmavathi, and A. Padmaja
Vol 000
Table 1
(Continued)
Anal. Calcd/Found
Compound
mp (ꢂC)
Yield (%)
Molecular formula (mol. wt)
(530.40)
C
H
N
43.07
47.78
47.81
49.88
49.85
41.76
41.80
47.99
48.04
50.08
50.05
41.92
41.96
49.27
49.30
51.25
51.23
43.17
43.22
47.70
47.74
49.70
49.76
41.96
41.92
47.90
47.93
49.89
49.95
42.11
42.15
49.66
49.69
51.73
51.78
43.19
43.15
47.99
47.96
50.08
50.11
41.91
41.96
48.19
48.17
50.29
50.33
42.07
42.10
3.21
4.01
4.04
4.58
4.59
3.14
3.12
4.45
4.48
5.00
4.99
3.52
3.55
3.51
3.49
4.11
4.12
2.72
2.75
3.40
3.39
3.98
4.01
2.64
2.66
3.82
3.80
4.38
4.39
3.00
3.03
3.73
3.74
4.34
4.37
2.86
2.84
3.60
3.63
4.20
4.22
2.78
2.77
4.04
4.07
4.62
4.60
3.16
3.18
13.16
13a
13b
13c
14a
14b
14c
15a
15b
15c
16a
16b
16c
17a
17b
17c
18a
18b
18c
19a
19b
19c
20a
20b
20c
181–183
190–192
202–204
185–187
193–195
206–208
196–198
202–204
213–215
223–225
232–234
240–242
229–231
245–247
250–252
197–199
209–211
216–218
213–215
224–226
239–241
232–234
243–245
254–256
75
73
77
72
69
74
67
69
74
70
72
78
80
71
82
66
64
73
65
67
75
72
75
78
C
19H19N5O4S3
(477.58)
14.66
14.72
13.85
13.89
12.82
12.90
20.62
20.67
19.47
19.58
18.01
18.10
14.37
14.43
13.58
13.53
12.59
12.66
13.91
13.95
13.17
13.23
12.23
12.20
19.55
19.63
18.51
18.57
17.19
17.26
15.24
15.32
14.36
14.31
13.25
13.32
14.73
14.82
13.91
13.88
12.86
12.93
20.71
20.82
19.55
19.63
18.08
18.14
C21H23N5O4S3
(505.63)
C19H17Cl2N5O4S3
(546.47)
C19H21N7O4S2
(475.54)
C21H25N7O4S2
(503.60)
C19H19Cl2N7O4S2
(544.43)
C20H17N5O6S2
(487.51)
C22H21N5O6S2
(515.56)
C20H15Cl2N5O6S2
(556.40)
C20H17N5O5S3
(503.57)
C22H21N5O5S3
(531.63)
C20H15Cl2N5O5S3
(572.46)
C20H19N7O5S2
(501.54)
C22H23N7O5S2
(529.59)
C20H17Cl2N7O5S2
(570.43)
C19H17N5O5S2
(459.50)
C21H21N5O5S2
(487.55)
C19H15Cl2N5O5S2
(528.39)
C19H17N5O4S3
(475.56)
C21H21N5O4S3
(503.62)
C19H15Cl2N5O4S3
(544.45)
C19H19N7O4S2
(473.53)
C21H23N7O4S2
(501.58)
C19H17Cl2N7O4S2
(542.42)
5-(30-aroyl-10H-pyrazol-40-ylsulfonylmethyl)-1,3,4-oxadiazole
(15), 2-(arylaminosulfonylmethyl)-5-(30-aroyl-10H-pyrazol-40
-ylsulfonyl-methyl)-1,3,4-thiadiazole (16), and 4-amino-3-
(arylaminosulfonylmethyl)-5-(30-aroyl-10H-pyrazol-40-ylsulfo-
nylmethyl)-1,2,4-triazole (17). Absence of AMX splitting
pattern due to pyrazoline ring protons in H NMR spectra
of 15, 16, and 17 indicated that aromatization occurred.
Further, the a,b-unsaturated ketone functionality in 3, 4,
attached to C-2/3 and C-5. The three double doublets observed
at d 4.61, 4.25, 3.59 in 9a, at 4.71, 4.24, 3.62 in 10a, and at
4.58, 4.21, 3.68 ppm in 11a were assigned to HA, HM, and
HX, respectively. Coupling constant values JAM ꢀ 12.2, JAX
5.8, and JMX ꢀ 10.4 Hz indicated that HA, HM are cis, HA,
HX are trans whereas HM, HX are geminal (Table 3). Dehydro-
genation of compounds 9, 10, and 11 with chloranil in xylene
gave the aromatized products 2-(arylaminosulfonylmethyl)-
1
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Synthesis of a New Class of Sulfonamido Bis Heterocycles
Scheme 2
R
O
N
N
O
O
O
O
S
S
N
H
X
4' 3'
2'
5'
1'
R
N
6 / 7 / 8
i
H
3 / 4 / 5
iii
ii
R
R
R
R
R
R
O
N
N
N
N
O
O
O
O
O
O
O
HA
O
O
S
S
S
S
S
S
S
4'
N
H
X
3'
N
H
5'
1'
4'
X
3'
MH
2'
2' N
5'
1'
N
N
N
H
HX
H
12 / 13 / 14
9 / 10 / 11
iv
iv
R
O
N
N
N
N
O
O
O
O
O
O
O
S
N
H
X
N
H
X
N
N
N
R
N
H
H
15 / 16 / 17
18 / 19 / 20
(i) TosMIC / NaH / DMSO / Et2O
(ii) CH2N2 / Et3N / Et2O
(iii) NH2NH2.H2O / MeOH
(iv) Chloranil / Xylene
3, 6, 9, 12, 15, 18 : X = O
4, 7, 10, 13, 16, 19 : X = S
5, 8, 11, 14, 17, 20 : X = N-NH2
R a) H
b) Me
c) Cl
and 5 was exploited to achieve a differently substituted
pyrazoline ring by [2 + 3] cyclocondensation between 3, 4,
5, and hydrazine hydrate in methanol. Thus, the compounds
2-(arylaminosulfonylmethyl)-5-(30-aryl-40,50-dihydro-10
H-pyrazol-50-ylsulfonyl-methyl)-1,3,4-oxadiazole (12), 2-(ary-
laminosulfonylmethyl)-5-(30-aryl-40,50-dihydro-10H-pyrazol-50
-ylsulfonylmethyl)-1,3,4-thiadiazole (13), and 4-amino-3-
(arylaminosulfonylmethyl)-5-(30-aryl-40,50-dihydro-10H-pyrazol-50
-ylsulfonylmethyl)-1,2,4-triazole (14) were prepared. The
1H NMR spectra of compounds 12a, 13a, and 14a showed
a doublet at d 3.51, 3.62, 3.59, a multiplet at 4.63–4.67,
4.71–4.74, and 4.67–4.70 ppm for methylene and methine
protons of pyrazoline ring. Aromatization of 12, 13, and
14 with chloranil in xylene resulted in 2-(arylaminosulfonyl-
methyl)-5-(30-aryl-10H-pyrazol-50-ylsulfonylmethyl)-1,3,4-
oxadiazole (18), 2-(arylaminosulfonylmethyl)-5-(30-aryl-10
H-pyrazol-50-ylsulfonylmethyl)-1,3,4-thiadiazole (19), and
4-amino-3-(arylaminosulfonylmethyl)-5-(30-aryl-10H-pyrazol-50
-ylsulfonylmethyl)-1,2,4-triazole (20) (Scheme 2 and Table 1).
The 1H NMR spectra of 18a, 19a, and 20a displayed
in Table 2. The 13C NMR spectra of the compounds exhib-
ited signals for different carbons as shown in Table 3.
CONCLUSIONS
A new class of sulfonamide bis heterocycles-pyrrolyl/pyr-
azolyl-1,3,4-oxadiazoles, 1,3,4-thiadiazoles, and 1,2,4-tria-
zoles was synthesized from unsaturated oxadiazoles. The
latter were prepared by intermolecular cyclocondensation of
arylaminosulfonylacetic acid hydrazide with E-aroylethene-
sulfonylacetic acid. The interconversion of oxadiazole to
thiadiazole and triazole was effected in the presence of appro-
priate nucleophiles. The olefin moiety present in these com-
pounds was used to develop pyrrole and pyrazole rings by
[2+ 3] cycloaddition and cyclocondensation methodologies.
EXPERIMENTAL
General. Melting points were determined in open capillaries
on a Mel-Temp apparatus (India) and are uncorrected. The purity
of the compounds was checked by TLC (silica gel H, BDH,
hexane/ethyl acetate, 3 : 1). The IR spectra were run on a Thermo
Nicolet IR 200 FT-IR spectrometer (USA) as KBr pellets and the
wavenumbers were given in cmꢁ1. The 1H NMR spectra were
recorded in CDCl3/DMSO-d6 on a Jeol JNM l-400MHz. The
13C NMR spectra (England) were recorded in CDCl3/DMSO-d6
0
signal for C4 -H at downfield region and merged with
aromatic protons in addition to singlets due to methylene
protons (Table 3). The IR spectra of the compounds syn-
thesized displayed absorption bands for different functional
groups at the expected regions and the values are depicted
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. Muralikrishna, G. Mallikarjuna Reddy, G. Lavanya, V. Padmavathi, and A. Padmaja
Vol 000
Table 2
IR data of compounds 3–20.
IR (KBr) cmꢁ1
Compound
SO2
C═N
C═C
C═O
NH
NH2
3a
3b
3c
4a
4b
4c
5a
5b
5c
6a
6b
6c
7a
7b
7c
8a
1146
1142
1149
1140
1136
1147
1138
1131
1142
1129
1125
1135
1141
1132
1146
1137
1130
1145
1144
1139
1149
1132
1135
1142
1135
1131
1142
1121
1118
1126
1124
1128
1130
1126
1122
1132
1138
1129
1140
1123
1119
1127
1132
1125
1136
1134
1127
1135
1128
1125
1136
1135
1130
1141
1307
1311
1317
1312
1319
1324
1315
1312
1320
1329
1323
1332
1324
1318
1326
1327
1322
1334
1338
1333
1342
1326
1328
1336
1308
1315
1321
1319
1313
1321
1327
1322
1334
1330
1327
1338
1324
1321
1330
1342
1336
1345
1324
1326
1334
1324
1320
1325
1329
1332
1335
1331
1327
1339
1569
1567
1576
1571
1563
1574
1562
1564
1570
1582
1577
1586
1588
1585
1594
1596
1592
1602
1576
1579
1581
1594
1589
1597
1607
1602
1608
1573
1568
1575
1584
1577
1589
1592
1586
1594
1583
1581
1593
1595
1598
1607
1609
1604
1610
1567
1571
1578
1573
1566
1577
1589
1583
1596
1626
1625
1631
1630
1624
1631
1625
1623
1628
1627
1629
1634
1622
1617
1625
1631
1628
1632
—
—
—
—
—
—
—
—
—
1668
1663
1671
1673
1670
1678
1674
1673
1680
1665
1668
1672
1671
1669
1676
1674
1672
1682
1671
1674
1679
1675
1673
1681
1678
1677
1685
—
—
—
—
—
—
—
—
—
1676
1672
1680
1674
1679
1683
1680
1685
1688
—
3218
3211
3231
3234
3229
3241
3247
3244
3253
3249
3242
3256
3234
3232
3239
3257
3258
3269
3253
3248
3261
3266
3269
3274
3251
3247
3269
3231
3224
3237
3229
3233
3244
3246
3238
3241
3273
3276
3275
3268
3263
3277
3263
3258
3267
3250
3243
3255
3261
3257
3266
3256
3249
3271
—
—
—
—
—
—
3349, 3462
3354, 3457
3356, 3464
—
—
—
—
—
—
3326, 3441
3331, 3433
3335, 3446
8b
8c
9a
9b
—
—
—
—
—
—
9c
10a
10b
10c
11a
11b
11c
12a
12b
12c
13a
13b
13c
14a
14b
14c
15a
15b
15c
16a
16b
16c
17a
17b
17c
18a
18b
18c
19a
19b
19c
20a
20b
20c
3362, 3473
3361, 3469
3371, 3478
—
—
—
—
—
—
—
—
—
—
—
—
—
—
3351, 3476
3347, 3459
3359, 3478
—
1638
1639
1643
1635
1634
1640
1637
1628
1633
1631
1624
1635
1633
1635
1641
1626
1619
1630
—
—
—
—
—
—
3332, 3456
3325, 3451
3339, 3458
—
—
—
—
—
—
—
—
—
—
—
—
—
—
3338, 3470
3341, 3456
3346, 3473
on a Jeol JNM spectrometer operating at 100MHz. All chemical
shifts are reported in d (ppm) using TMS as an internal standard.
The microanalyses were performed on a Perkin-Elmer 240C
elemental analyzer (USA). The mass spectra were recorded on
Jeol JMS-D 300, Finnigan Mat B 1210 at 70eV with an emission
current of 100 mA and Agilent 6310 Ion Trap with positive scan
mode. The starting compound E-aroylethenesulfonylacetic acid
(2) was prepared by the literature procedure [24].
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Synthesis of a New Class of Sulfonamido Bis Heterocycles
Table 3
1H, 13C NMR, and mass data of compounds 3–20.
Compound
1H NMR (CDCl3/DMSO-d6) d, (ppm)
13C NMR (CDCl3/DMSO-d6) d, (ppm)
MS (m/z)
M+. 447
3a
5.02 (s, 2H, CH2-(C-5)), 5.61 (s, 2H,
CH2-(C-2)), 7.10 (d, 1H, HB,
J = 13.8 Hz), 7.21-7.91 (m, 11H, HA
and Ar-H), 10.32 (bs, 1H, NH)
2.24 and 2.32 (s, 6H, Ar-CH3), 4.91
(s, 2H, CH2-(C-5)), 5.38
(s, 2H, CH2-(C-2)), 6.87 (d, 1H, HB,
J = 13.7 Hz), 7.14–7.67 (m, 9H, HA
and Ar-H), 10.29 (bs, 1H, NH)
4.98 (s, 2H, CH2-(C-5)), 5.69
(s, 2H, CH2-(C-2)),
6.99 (d, 1H, HB, J= 14.0 Hz), 7.23–7.91
(m, 9H, HA and Ar-H), 10.39 (bs, 1H, NH) 130.4, 133.6 (aromatic carbons)
5.14 (s, 2H, CH2-(C-5)), 5.42 (s, 2H,
CH2-(C-2)), 6.87 (d, 1H, HB,
J = 13.9 Hz), 7.27–7.86 (m, 11H, HA
and Ar-H), 10.41 (bs, 1H, NH)
2.28 and 2.39 (s, 6H, Ar-CH3), 5.16
(s, 2H, CH2-(C-5)), 5.38 (s, 2H, CH2-
(C-2)), 6.88 (d, 1H, HB, J = 13.7 Hz),
7.21–7.79 (m, 9H, HA and Ar-H),
10.39 (bs, 1H, NH)
44.2 (CH2-(C-5)), 50.1 (CH2-(C-2)), 121.4
(C-HB), 145.6 (C-HA), 158.5 (C-5), 160.2 (C-2),
178.7 (C═O), 126.5, 127.2, 127.8, 128.6, 129.9,
130.5, 131.4, 133.1 (aromatic carbons)
20.9 and 22.0 (Ar-CH3), 43.8 (CH2-(C-5)),
49.7 (CH2-(C-2)), 120.7 (C-HB), 144.4 (C-HA),
157.6 (C-5), 160.4 (C-2), 180.9 (C═O), 124.4,
125.1, 125.7, 128.5, 129.4, 131.2, 131.9, 133.4
(aromatic carbons)
3b
—
—
3c
4a
4b
45.1 (CH2-(C-5)), 50.8 (CH2-(C-2)), 122.3 (C-HB),
146.7 (C-HA), 159.3 (C-5), 161.7 (C-2), 181.9
(C═O), 125.2, 126.3, 127.0, 127.6, 128.3, 129.4,
45.2 (CH2-(C-5)), 52.6 (CH2-(C-2)), 124.7 (C-HB),
M+. 463
145.4 (C-HA), 158.5 (C-5), 159.8 (C-2), 180.3
(C═O), 125.7, 126.4, 127.5, 128.1, 128.7, 129.3,
130.4, 132.9 (aromatic carbons)
21.3 and 22.1 (Ar-CH3), 42.8 (CH2-(C-5)), 52.1
(CH2-(C-2)), 123.6 (C-HB), 144.8 (C-HA), 159.6 (C-5),
160.4 (C-2), 181.2 (C═O), 124.8, 126.0, 126.6, 127.3,
128.3, 129.5, 130.6, 133.1 (aromatic carbons)
—
—
4c
5a
5.27 (s, 2H, CH2-(C-5)), 5.47 (s, 2H,
CH2-(C-2)), 7.04 (d, 1H, HB,
43.7 (CH2-(C-5)), 53.2 (CH2-(C-2)), 125.1 (C-HB),
145.9 (C-HA), 158.7 (C-5), 160.2 (C-2), 183.5 (C═O),
126.1, 126.7, 127.3, 128.5, 129.0, 129.8, 130.7, 132.8
(aromatic carbons)
47.2 (CH2-(C-5)), 52.0 (CH2-(C-3)), 122.6 (C-HB),
143.7 (C-HA), 158.2 (C-5), 159.6 (C-3), 182.6 (C═O),
125.7, 126.3, 126.9, 127.5, 128.6, 129.6, 130.1, 132.5
(aromatic carbons)
J = 14.3 Hz), 7.27-7.91 (m, 9H, HA
and Ar-H), 10.48 (bs, 1H, NH)
5.19 (s, 2H, CH2-(C-5)), 5.43 (s, 2H,
CH2-(C-3)), 5.75 (bs, 2H, NH2), 6.81
(d, 1H, HB, J = 14.1 Hz), 7.19–7.72
(m, 11H, HA and Ar-H), 10.37
(bs, 1H, NH)
M+. 461
5b
2.30 and 2.41 (s, 6H, Ar-CH3), 5.21
(s, 2H, CH2-(C-5)), 5.39 (s, 2H, CH2-
(C-3)), 5.69 (bs, 2H, NH2), 6.76 (d, 1H,
HB, J = 14.3 Hz), 7.29–7.98 (m, 9H, HA
and Ar-H), 10.27 (bs, 1H, NH)
5.12 (s, 2H, CH2-(C-5)), 5.40 (s, 2H,
21.3 and 22.6 (Ar-CH3), 45.2 (CH2-(C-5)), 51.8
(CH2-(C-3)), 123.0 (C-HB), 142.6 (C-HA),
159.1 (C-5), 160.2 (C-3), 181.7 (C═O), 126.0,
126.7, 127.3, 128.4, 129.6, 130.3, 131.4, 133.2
(aromatic carbons)
—
—
5c
6a
46.6 (CH2-(C-5)), 51.9 (CH2-(C-3)), 123.7 (C-HB),
CH2-(C-3)), 5.81 (bs, 2H, NH2), 6.85 (d, 143.5 (C-HA), 158.6 (C-5), 159.5 (C-3), 183.1
1H, HB, J = 14.5 Hz), 7.29–7.89 (m, 9H,
HA and Ar-H), 10.43 (bs, 1H, NH)
5.21 (s, 2H, CH2-(C-5)), 5.39 (s, 2H,
(C═O), 126.5, 127.8, 128.8, 129.2, 129.9, 130.6,
131.3, 133.6 (aromatic carbons)
46.2 (CH2-(C-5)), 49.7 (CH2-(C-2)), 108.5 (C-30),
112.3 (C-40), 119.8 (C-50), 123.4 (C-20), 156.8 (C-5),
159.4 (C-2), 173.6 (C═O), 125.3, 126.4, 127.6,
128.1, 129.3, 130.8, 132.5, 134.3 (aromatic carbons)
M+. 486
0
CH2-(C-2)), 6.71 (s, 1H, C5 -H),
0
7.24–7.92 (m, 11H, C2 -H and
Ar-H), 8.82 (bs, 1H, NH), 10.37
(bs, 1H, NH-SO2)
6b
2.21 and 2.29 (s, 6H, Ar-CH3), 5.18
(s, 2H, CH2-(C-5)), 5.31 (s, 2H, CH2-
22.0 and 23.2 (Ar-CH3), 45.4 (CH2-(C-5)), 51.5
(CH2-(C-2)), 107.9 (C-30), 111.5 (C-40), 118.2 (C-50),
122.6 (C-20), 156.4 (C-5), 158.6 (C-2), 173.1 (C═O),
125.1, 127.3, 128.6, 129.7, 130.4, 132.7, 133.4, 135.7
(aromatic carbons)
M+. (+ve scan) 515.2
0
(C-2)), 6.64 (s, 1H, C5 -H), 7.21–7.82
0
(m, 9H, C2 -H and Ar-H), 8.75 (bs, 1H,
NH), 10.41 (bs, 1H, NH-SO2)
6c
7a
5.30 (s, 2H, CH2-(C-5)), 5.41 (s, 2H,
46.5 (CH2-(C-5)), 52.1 (CH2-(C-2)), 109.2 (C-30),
113.4 (C-40), 120.1 (C-50), 124.5 (C-20), 157.2 (C-5),
159.8 (C-2), 174.5 (C═O), 126.8, 127.5, 129.4,
130.0, 130.7, 131.5, 133.6, 135.4 (aromatic carbons)
46.3 (CH2-(C-5)), 52.4 (CH2-(C-2)), 105.9 (C-30),
113.5 (C-40), 116.8 (C-50), 122.5 (C-20), 156.5 (C-5),
159.4 (C-2), 177.8 (C═O), 127.4, 128.1, 128.8,
129.4, 130.9, 131.4, 132.8, 136.1 (aromatic carbons)
M++2 (+ve scan)
557.8
0
CH2-(C-2)), 6.75 (s, 1H, C5 -H), 7.42–
0
7.88 (m, 9H, C2 -H and Ar-H), 8.91
(bs, 1H, NH), 10.28 (bs, 1H, NH-SO2)
5.12 (s, 2H, CH2-(C-5)), 5.34 (s, 2H,
M+. 502
0
CH2-(C-2)), 6.83 (s, 1H, C5 -H),
0
7.16–7.85 (m, 11H, C2 -H and Ar-H),
8.46 (bs, 1H, NH), 10.41 (bs, 1H,
NH-SO2)
2.18 and 2.28 (s, 6H, Ar-CH3), 5.15
(s, 2H, CH2-(C-5)), 5.23 (s, 2H, CH2-
7b
20.8 and 21.9 (Ar-CH3), 45.4 (CH2-(C-5)), 51.8
M+.(+ve scan) 531.4
(CH2-(C-2)), 105.7 (C-30), 112.6 (C-40), 115.4 (C-50),
(Continued)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. Muralikrishna, G. Mallikarjuna Reddy, G. Lavanya, V. Padmavathi, and A. Padmaja
Vol 000
Table 3
(Continued)
Compound
1H NMR (CDCl3/DMSO-d6) d, (ppm)
13C NMR (CDCl3/DMSO-d6) d, (ppm)
MS (m/z)
0
(C-2)), 6.81 (s, 1H, C5 -H), 7.11–7.90
121.8 (C-20), 155.8 (C-5), 158.3 (C-2), 176.1 (C═O),
125.8, 126.3, 127.2, 127.9, 129.4, 130.6, 132.5,
135.9 (aromatic carbons)
0
(m, 9H, C2 -H and Ar-H), 8.25 (bs, 1H,
NH), 10.36
(bs, 1H, NH-SO2)
5.19 (s, 2H, CH2-(C-5)), 5.35 (s, 2H,
CH2-(C-2)), 6.91 (s, 1H, C5 -H),
7.17–7.83 (m, 9H, C2 -H and Ar-H),
7c
8a
8b
47.3 (CH2-(C-5)), 52.9 (CH2-(C-2)), 106.1 (C-30),
113.9 (C-40), 116.2 (C-50), 122.7 (C-20), 157.1 (C-5),
161.0
M++2 (+ve scan)
573.9
0
0
8.37 (bs, 1H, NH), 10.48 (bs, 1H,
NH-SO2)
5.23 (s, 2H, CH2-(C-5)), 5.35 (s, 2H,
(C-2), 178.3 (C═O), 127.2, 128.5, 129.1, 129.7, 130.3,
131.7, 133.0, 136.4 (aromatic carbons)
47.5 (CH2-(C-5)), 53.1 (CH2-(C-3)), 106.1 (C-30), 109.4
(C-40), 115.6 (C-50), 124.5 (C-20), 156.1 (C-5), 159.5 (C-3),
180.4 (C═O), 126.6, 127.5, 129.3, 130.5, 131.3, 132.7,
135.4, 136.8 (aromatic carbons)
M+. 500
CH2-(C-3)), 5.58 (bs, 2H, NH2), 6.79
0
0
(s, 1H, C5 -H), 7.21–7.86 (m, 11H, C2 -
H and Ar-H), 8.43 (bs, 1H, NH), 10.46
(bs, 1H, NH-SO2)
2.26 and 2.34 (s, 6H, Ar-CH3), 5.16
(s, 2H, CH2-(C-5)), 5.29 (s, 2H, CH2-
(C-3)), 5.57 (bs, 2H, NH2), 6.76 (s, 1H,
21.1 and 22.3 (Ar-CH3), 46.9 (CH2-(C-5)), 52.6 (CH2-
(C-3)), 105.4 (C-30), 108.6 (C-40), 114.7 (C-50), 123.6
(C-20), 155.4 (C-5), 158.6 (C-3), 180.0 (C═O), 125.4,
126.2, 126.8, 127.3, 128.6, 129.4, 132.7, 135.4
(aromatic carbons)
M+. (+ve scan) 529.5
0
0
C5 -H), 7.18–7.81 (m, 9H, C2 -H and
Ar-H), 8.36 (bs, 1H, NH), 10.30
(bs, 1H, NH-SO2)
8c
9a
5.25 (s, 2H, CH2-(C-5)), 5.42 (s, 2H,
CH2-(C-3)), 5.69 (bs, 2H, NH2), 6.85
48.4 (CH2-(C-5)), 53.6 (CH2-(C-3)), 106.8 (C-30), 110.5
(C-40), 116.1 (C-50), 124.9 (C-20), 156.7 (C-5), 159.8
(C-3), 181.6 (C═O), 126.2, 127.5, 128.1, 129.5, 130.4,
132.1, 132.8, 135.7 (aromatic carbons)
M++2 (+ve scan)
571.7
0
0
(s, 1H, C5 -H), 7.24–7.92 (m, 9H, C2 -H
and Ar-H), 8.45 (bs, 1H, NH), 10.51
(bs, 1H, NH-SO2)
3.59 (dd, 1H, HX, JAX = 5.8 Hz,
48.2 (CH2-(C-5)), 52.1 (CH2-(C-2)), 53.8 (C-50), 68.0
C-40), 154.5 (C-30), 157.9 (C-5), 159.8 (C-2), 181.3
(C═O), 126.9, 128.3, 129.0, 129.6, 130.4, 132.3,
133.5, 136.7 (aromatic carbons)
M+. 489
JMX = 10.4 Hz), 4.25 (dd, 1H, HM,
JAM = 12.2 Hz), 4.61 (dd, 1H, HA), 5.08
(s, 2H, CH2-(C-5)), 5.28 (s, 2H, CH2-
(C-2)), 7.19–7.86 (m, 10H, Ar-H), 9.95
(bs, 1H, NH), 10.62 (bs, 1H, NH-SO2)
2.22 and 2.31 (s, 6H, Ar-CH3), 3.57
(dd, 1H, HX, JAX = 5.7 Hz,
JMX = 10.1 Hz), 4.18 (dd, 1H, HM,
JAM = 12.0 Hz), 4.59 (dd, 1H, HA), 4.89
(s, 2H, CH2-(C-5)), 5.31 (s, 2H, CH2-(C-
2)), 7.16–7.83 (m, 8H, Ar-H), 9.93 (bs,
1H, NH), 10.57 (bs, 1H, NH-SO2)
3.62 (dd, 1H, HX, JAX = 6.1 Hz,
JMX = 10.8 Hz), 4.29 (dd, 1H, HM,
JAM = 12.4 Hz), 4.68 (dd, 1H, HA), 5.02
(s, 2H, CH2-(C-5)), 5.35 (s, 2H, CH2-
(C-2)), 7.21–7.91 (m, 8H, Ar-H), 10.01
(bs, 1H, NH), 10.65 (bs, 1H, NH-SO2)
3.62 (dd, 1H, HX, JAX = 6.0 Hz,
JMX = 9.8 Hz), 4.24 (dd, 1H, HM,
JAM = 11.8 Hz), 4.71 (dd, 1H, HA), 4.97
(s, 2H, CH2-(C-5)), 5.36 (s, 2H, CH2-
(C-2)), 7.23–7.82 (m, 10H, Ar-H), 9.95
(bs, 1H, NH), 10.54 (bs, 1H, NH-SO2)
9b
21.0 and 21.8 (Ar-CH3), 46.0 (CH2-(C-5)), 51.8 (CH2-
(C-2)), 53.1 (C-50), 69.1 (C-40), 153.5 (C-30), 157.2
(C-5), 159.5 (C-2), 180.6 (C═O), 124.1, 125.5, 126.3,
127.8, 130.5, 131.7, 133.9, 135.4 (aromatic carbons)
—
9c
47.5 (CH2-(C-5)), 52.4 (CH2-(C-2)), 54.2 (C-50), 68.5
(C-40), 154.2 (C-30), 159.0 (C-5), 160.2 (C-2), 183.0
(C═O), 127.2, 128.1, 128.7, 129.3, 130.6, 132.4,
133.5, 134.9 (aromatic carbons)
—
M+. 505
—
10a
10b
49.4 (CH2-(C-5)), 52.1 (CH2-(C-2)), 53.2 (C-50), 66.4
(C-40), 153.4 (C-30), 157.1 (C-5), 159.2 (C-2), 182.4
(C═O), 126.8, 127.4, 129.0, 129.8, 131.5, 132.6,
134.6, 136.2 (aromatic carbons)
2.24 and 2.30 (s, 6H, Ar-CH3), 3.57 (dd, 20.6 and 21.8 (Ar-CH3), 48.7 (CH2-(C-5)), 51.5 (CH2
1H, HX, JAX = 5.9 Hz, JMX = 10.2 Hz),
4.18 (dd, 1H, HM, JAM = 11.6 Hz), 4.68
(dd, 1H, HA), 4.89 (s, 2H, CH2-(C-5)),
5.30 (s, 2H, CH2-(C-2)), 7.21–7.74 (m,
8H, Ar-H), 9.98 (bs, 1H, NH), 10.48 (bs,
1H, NH-SO2)
-(C-2)), 53.6 (C-50), 65.8 (C-40), 152.7 (C-30), 157.5
(C-5), 159.0 (C-2), 182.2 (C═O), 127.1, 127.8, 129.4,
130.5, 131.8, 132.4, 133.6, 136.5 (aromatic carbons)
10c
3.65 (dd, 1H, HX, JAX = 6.2 Hz,
49.6 (CH2-(C-5)), 52.8 (CH2-(C-2)), 53.9 (C-50), 66.7
(C-40), 154.1 (C-30), 157.9 (C-5), 160.5 (C-2), 185.1
(C═O), 126.7, 127.4, 128.8, 129.5, 130.1, 130.7,
132.6, 135.8 (aromatic carbons)
—
JMX = 10.3 Hz), 4.25 (dd, 1H, HM,
JAM = 12.0 Hz), 4.74 (dd, 1H, HA), 5.01
(s, 2H, CH2-(C-5)), 5.42 (s, 2H, CH2-
(Continued)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Synthesis of a New Class of Sulfonamido Bis Heterocycles
Table 3
(Continued)
Compound
1H NMR (CDCl3/DMSO-d6) d, (ppm)
13C NMR (CDCl3/DMSO-d6) d, (ppm)
MS (m/z)
(C-2)), 7.26–7.78 (m, 8H, Ar-H), 10.02
(bs, 1H, NH), 10.61 (bs, 1H, NH-SO2)
3.68 (dd, 1H, HX, JAX = 6.1 Hz,
JMX = 10.1 Hz), 4.21 (dd, 1H, HM,
JAM = 12.2 Hz), 4.58 (dd, 1H, HA), 5.12
(s, 2H, CH2-(C-5)), 5.32 (s, 2H, CH2-
(C-3)), 5.79 (bs, 2H, NH2), 7.21-7.82
(m, 10H, Ar-H), 9.32 (bs, 1H, NH),
10.35 (bs, 1H, NH-SO2)
11a
46.9 (CH2-(C-5)), 51.7 (CH2-(C-3)), 53.1 (C-50), 66.8
(C-40), 153.3 (C-30), 158.6 (C-5), 159.5 (C-3), 181.9
(C═O), 125.4, 126.7, 127.5, 128.1, 128.6, 129.5,
131.3, 134.5 (aromatic carbons)
M+. 503
11b
11c
2.18 and 2.25 (s, 6H, Ar-CH3), 3.59
(dd, 1H, HX, JAX = 6.3 Hz,
21.1 and 22.5 (Ar-CH3), 46.1 (CH2-(C-5)), 51.5 (CH2-
(C-3)), 52.8 (C-50), 66.4 (C-40), 152.9 (C-30), 158.1 (C-5),
159.7 (C-3), 182.6 (C═O), 127.7, 128.3, 129.5, 130.4,
131.2, 131.9, 133.4, 136.8 (aromatic carbons)
—
JMX = 10.4 Hz), 4.18 (dd, 1H, HM,
JAM = 12.3 Hz), 4.49 (dd, 1H, HA), 5.09
(s, 2H, CH2-(C-5)), 5.26 (s, 2H, CH2-
(C-3)), 5.68 (bs, 2H, NH2), 7.19–7.80
(m, 8H, Ar-H), 9.41 (bs, 1H, NH), 10.41
(bs, 1H, NH-SO2)
3.73 (dd, 1H, HX, JAX = 6.2 Hz,
JMX = 10.5 Hz), 4.25 (dd, 1H, HM,
JAM = 12.1 Hz), 4.61 (dd, 1H, HA), 5.23
(s, 2H, CH2-(C-5)), 5.35 (s, 2H, CH2-
(C-3)), 5.88 (bs, 2H, NH2), 7.23–7.76
(m, 8H, Ar-H), 9.48 (bs, 1H, NH), 10.56
(bs, 1H, NH-SO2)
47.0 (CH2-(C-5)), 51.9 (CH2-(C-3)), 53.6 (C-50), 67.2
(C-40), 154.1 (C-30), 158.5 (C-5), 159.3 (C-3), 183.6
(C═O), 128.2, 129.4, 130.0, 130.7, 131.5, 132.5, 134.7,
136.3 (aromatic carbons)
—
12a
12b
3.51 (d, 2H, C4 -H), 4.63–4.67 (m, 1H,
41.4 (C-40), 48.7 (CH2-(C-5)), 52.0 (CH2-(C-2)), 64.3
(C-50), 154.8 (C-30), 156.8 (C-5), 159.1 (C-2), 126.5, 127.3,
128.1, 128.8, 129.6, 130.4, 132.6, 134.5 (aromatic carbons)
M+. 461
M+. 477
M+. 475
0
0
C5 -H), 5.13 (s, 2H, CH2-(C-5)), 5.41
(s, 2H, CH2-(C-2)), 7.14–7.69 (m, 10H,
Ar-H), 9.41 (bs, 1H, NH), 10.16 (bs, 1H,
NH-SO2)
2.23 and 2.28 (s, 6H, Ar-CH3), 3.46
21.0 and 21.4 (Ar-CH3), 40.6 (C-40), 48.3 (CH2-(C-5)),
51.5 (CH2-(C-2)), 62.9 (C-50), 154.2 (C-30), 156.6 (C-5),
—
—
0
0
(d, 2H, C4 -H), 4.60–4.63 (m, 1H, C5 -
H), 5.11 (s, 2H, CH2-(C-5)), 5.35 (s, 2H, 158.6 (C-2), 126.3, 127.0, 128.2, 128.9, 131.2, 132.4,
CH2-(C-2)), 7.09–7.62 (m, 8H, Ar-H),
9.37 (bs, 1H, NH), 10.02 (bs, 1H, NH-
SO2)
133.5, 134.8 (aromatic carbons)
0
12c
13a
13b
3.54 (d, 2H, C4 -H), 4.65–4.68 (m, 1H,
43.7 (C-40), 49.5 (CH2-(C-5)), 52.3 (CH2-(C-2)), 64.7
(C-50), 155.3 (C-30), 157.3 (C-5), 159.4 (C-2), 127.1, 128.6,
129.3, 130.6, 131.7, 132.5, 133.4, 134.8 (aromatic carbons)
0
C5 -H), 5.18 (s, 2H, CH2-(C-5)), 5.31
(s, 2H, CH2-(C-2)), 7.21–7.75 (m, 8H,
Ar-H), -9.47 (bs, 1H, NH), 10.21 (bs,
1H, NH-SO2)
0
3.62 (d, 2H, C4 -H), 4.71–4.74 (m, 1H,
42.1 (C-40), 49.7 (CH2-(C-5)), 52.4 (CH2-(C-2)), 64.5
(C-50), 155.6 (C-30), 157.7 (C-5), 159.9 (C-2), 127.4, 128.1,
128.7, 129.5, 130.2, 131.6, 133.4, 135.4 (aromatic carbons)
0
C5 -H), 5.15 (s, 2H, CH2-(C-5)), 5.39
(s, 2H, CH2-(C-2)), 7.18–7.73 (m, 10H,
Ar-H), 9.63 (bs, 1H, NH), 10.23 (bs, 1H,
NH-SO2)
2.25 and 2.32 (s, 6H, Ar-CH3), 3.55
20.6 and 21.5 (Ar-CH3), 41.8 (C-40), 48.4 (CH2-(C-5)), 51.9
(CH2-(C-2)), 63.8 (C-50), 155.0 (C-30), 157.3 (C-5), 159.6
(C-2), 127.1, 128.2, 129.3, 130.7, 131.8, 133.4, 134.8,
137.2 (aromatic carbons)
—
—
0
0
(d, 2H, C4 -H), 4.69–4.72 (m, 1H, C5 -
H), 5.18 (s, 2H, CH2-(C-5)), 5.44
(s, 2H, CH2-(C-2)), 7.21–7.86 (m, 8H,
Ar-H), 9.65 (bs, 1H, NH), 10.18 (bs, 1H,
NH-SO2)
0
13c
14a
3.64 (d, 2H, C4 -H), 4.74–4.78 (m, 1H,
43.9 (C-40), 50.3 (CH2-(C-5)), 52.8 (CH2-(C-2)), 64.9
(C-50), 155.8 (C-30), 158.2 (C-5), 160.1 (C-2), 126.8, 127.5,
128.2, 129.6, 130.3, 130.9, 132.4, 136.5 (aromatic carbons)
0
C5 -H), 5.23 (s, 2H, CH2-(C-5)), 5.46
(s, 2H, CH2-(C-2)), 7.24–7.78 (m, 8H,
Ar-H), 9.71 (bs, 1H, NH), 10.34 (bs, 1H,
NH-SO2)
0
3.59 (d, 2H, C4 -H), 4.67–4.70 (m, 1H,
42.4 (C-40), 49.4 (CH2-(C-5)), 52.6 (CH2-(C-3)), 65.1
(C-50), 153.8 (C-30), 158.0 (C-5), 161.1 (C-3), 127.3, 128.1,
128.6, 129.3, 130.4, 131.5, 132.7, 135.2(aromatic carbons)
0
C5 -H), 5.20 (s, 2H, CH2-(C-5)), 5.43
(s, 2H, CH2-(C-3)), 5.63 (bs, 2H, NH2),
7.18–7.81 (m, 10H, Ar-H), 9.74 (bs, 1H,
NH), 10.31 (bs, 1H, NH-SO2)
(Continued)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. Muralikrishna, G. Mallikarjuna Reddy, G. Lavanya, V. Padmavathi, and A. Padmaja
Vol 000
Table 3
(Continued)
Compound
1H NMR (CDCl3/DMSO-d6) d, (ppm)
13C NMR (CDCl3/DMSO-d6) d, (ppm)
MS (m/z)
14b
2.24 and 2.33 (s, 6H, Ar-CH3), 3.63
(d, 2H, C4 -H), 4.76–4.79 (m, 1H, C5 -
21.1 and 21.8 (Ar-CH3), 42.7 (C-40), 49.2 (CH2-(C-5)),
52.1 (CH2-(C-3)), 64.6 (C-50), 152.9 (C-30), 157.6 (C-5),
—
0
0
H), 5.21 (s, 2H, CH2-(C-5)), 5.42 (s, 2H, 160.2 (C-3), 125.4, 126.3, 128.6, 129.2, 129.8, 130.5,
CH2-(C-3)), 5.61 (bs, 2H, NH2), 7.15–
7.74 (m, 8H, Ar-H), 9.76 (bs, 1H, NH),
10.27 (bs, 1H, NH-SO2)
132.4, 135.6 (aromatic carbons)
0
14c
3.67 (d, 2H, C4 -H), 4.78–4.82 (m, 1H,
44.3 (C-40), 51.1 (CH2-(C-5)), 53.0 (CH2-(C-3)), 65.8
(C-50), 154.5 (C-30), 158.2 (C-5), 161.3 (C-3), 126.7, 127.5,
128.4, 130.1, 130.7, 132.2, 133.6, 135.1 (aromatic carbons)
—
0
C5 -H), 5.27 (s, 2H, CH2-(C-5)), 5.48
(s, 2H, CH2-(C-3)), 5.72 (bs, 2H, NH2),
7.26–7.88 (m, 8H, Ar-H), 9.80 (bs, 1H,
NH), 10.36 (bs, 1H, NH-SO2)
15a
15b
5.17 (s, 2H, CH2-(C-5)), 5.35 (s, 2H,
CH2-(C-2)), 6.64 (bs, 1H, NH),
50.2 (CH2-(C-5)), 54.5 (CH2-(C-2)), 134.6 (C-50), 140.2
(C-40), 149.4 (C-30), 159.3 (C-5), 162.3 (C-2), 183.1
(C═O), 125.6, 126.3, 127.8, 128.4, 129.5, 131.7, 132.8,
135.5 (aromatic carbons)
M+. 487
0
6.98–7.61 (m, 11H, C5 -H and Ar-H),
10.35 (bs, 1H, NH-SO2)
2.16 and 2.23 (s, 6H, Ar-CH3), 5.14
(s, 2H, CH2-(C-5)), 5.36 (s, 2H, CH2-
(C-2)), 6.490 (bs, 1H, NH), 6.90–7.63
(m, 9H, C5 -H and Ar-H), 10.41
(bs, 1H, NH-SO2)
21.6 and 22.4 (Ar-CH3), 49.8 (CH2-(C-5)), 53.9 (CH2-
(C-2)), 133.8 (C-50), 139.6 (C-40), 148.6 (C-30), 158.7 (C-5),
161.4 (C-2), 183.5 (C═O), 126.7, 128.2, 128.9, 130.4,
132.6, 133.5, 134.5, 136.9 (aromatic carbons)
M+.(+ve scan) 516.4
15c
16a
16b
5.21 (s, 2H, CH2-(C-5)), 5.41
(s, 2H, CH2-(C-2)), 6.63 (bs, 1H, NH),
50.7 (CH2-(C-5)), 54.8 (CH2-(C-2)), 135.1 (C-50), 141.2
(C-40), 150.4 (C-30), 160.3 (C-5), 162.9 (C-2), 185.7
(C═O), 128.3, 129.5, 130.2, 130.7, 131.6, 132.4, 134.1,
136.3 (aromatic carbons)
M++2 (+ve scan)
558.9
0
7.03–7.61 (m, 9H, C5 -H and Ar-H),
10.47 (bs, 1H, NH-SO2)
5.32 (s, 2H, CH2-(C-5)), 5.50 (s, 2H,
CH2-(C-2)), 6.62 (bs, 1H, NH),
49.6 (CH2-(C-5)), 53.5 (CH2-(C-2)), 133.5 (C-50), 138.7
(C-40), 149.4 (C-30), 158.5 (C-5), 161.3 (C-2), 184.0
(C═O), 125.8, 126.3, 127.5, 128.6, 129.7, 130.4, 132.8,
135.4 (aromatic carbons)
M+. 503
0
7.05–7.68 (m, 11H, C5 -H and Ar-H),
10.38 (bs, 1H, NH-SO2)
2.19 and 2.30 (s, 6H, Ar-CH3), 5.27
(s, 2H, CH2-(C-5)), 5.42 (s, 2H, CH2-
21.0 and 21.9 (Ar-CH3), 48.5 (CH2-(C-5)), 52.8 (CH2-
(C-2)), 132.8 (C-50), 137.9 (C-40), 148.6 (C-30), 157.6
(C-5), 159.8 (C-2), 182.3 (C═O), 124.7, 125.4, 127.1,
M+.(+ve scan) 532.2
(C-2)), 6.58 (bs, 1H, NH), 7.01–7.67
0
(m, 9H, C5 -H and Ar-H), 10.29 (bs, 1H, 127.8, 129.3, 130.4, 132.5, 134.8 (aromatic carbons)
NH-SO2)
5.34 (s, 2H, CH2-(C-5)), 5.53
(s, 2H, CH2-(C-2)), 6.63 (bs, 1H, NH),
7.08–7.71 (m, 9H, C5 -H and Ar-H),
10.42 (bs, 1H, NH-SO2)
4.98 (s, 2H, CH2-(C-5)), 5.12 (s, 2H,
CH2-(C-3)), 5.64 (bs, 2H, NH2), 6.58
(bs, 1H, NH), 7.12–7.78 (m, 11H, C5 -H (C═O), 127.1, 128.4, 129.3, 130.0, 130.7, 131.6, 133.5,
16c
17a
17b
49.7 (CH2-(C-5)), 54.1 (CH2-(C-2)), 133.9 (C-50), 139.2
(C-40), 149.2 (C-30), 158.8 (C-5), 161.7 (C-2), 183.7
(C═O), 127.3, 128.4, 129.5, 130.1, 130.9, 132.3, 134.7,
136.1 (aromatic carbons)
M++2 (+ve scan)
575.1
0
48.8 (CH2-(C-5)), 51.6 (CH2-(C-3)), 133.6 (C-50), 139.5
(C-40), 148.5 (C-30), 158.7 (C-5), 160.1 (C-3), 185.4
M+.501
0
and Ar-H), 10.27 (bs, 1H, NH-SO2)
2.20 and 2.32 (s, 6H, Ar-CH3), 4.93 (s,
2H, CH2-(C-5)), 5.07 (s, 2H, CH2-(C-
3)), 5.54 (bs, 2H, NH2), 6.32 (bs, 1H,
135.0 (aromatic carbons)
20.4 and 21.6 (Ar-CH3), 47.9 (CH2-(C-5)), 51.8 (CH2-
(C-3)), 133.0 (C-50), 139.4 (C-40), 147.6 (C-30), 157.9
(C-5), 159.7 (C-3), 182.8 (C═O), 127.8, 128.7, 129.5,
131.3, 132.6, 133.4, 134.8, 136.5 (aromatic carbons)
M+.(+ve scan) 530.2
0
NH), 7.12–7.76 (m, 9H, C5 -H and Ar-
H), 10.19 (bs, 1H, NH-SO2)
17c
18a
18b
5.07 (s, 2H, CH2-(C-5)), 5.32 (s, 2H,
CH2-(C-3)), 5.87 (bs, 2H, NH2), 6.506
(bs, 1H, NH), 7.18–7.81 (m, 9H, C5 -H
and Ar-H), 10.39 (bs, 1H, NH-SO2)
4.98 (s, 2H, CH2-(C-5)), 5.24 (s, 2H,
CH2-(C-2)), 6.57 0(bs, 1H, NH), 7.17–
7.83 (m, 11H, C4 -H and Ar-H), 10.11
(bs, 1H, NH-SO2)
48.7 (CH2-(C-5)), 52.5 (CH2-(C-3)), 134.3 (C-50), 140.8
(C-40), 149.1 (C-30), 159.2 (C-5), 160.5 (C-3), 183.7
(C═O), 128.4, 129.5, 130.6, 131.8, 132.3, 132.4, 135.1,
136.2 (aromatic carbons)
M++2 (+ve scan)
572.8
50.4 (CH2-(C-5)), 52.6 (CH2-(C-2)), 135.1 (C-40), 139.3
(C-50), 146.5 (C-30), 159.3 (C-5), 161.8 (C-2), 125.2, 126.4,
127.0, 127.7, 128.4, 129.5, 130.3, 133.6 (aromatic carbons)
M+. 459
2.20 and 2.28 (s, 6H, Ar-CH3), 5.03 (s,
2H, CH2-(C-5)), 5.21 (s, 2H, CH2-(C-
2)), 6.53 (bs, 1H, NH), 7.11–7.90 (m,
20.3 and 20.9 (Ar-CH3), 49.7 (CH2-(C-5)), 52.2 (CH2-
(C-2)), 134.6 (C-40), 138.7 (C-50), 145.4 (C-30), 158.7
(C-5), 161.1 (C-2), 126.5, 127.2, 128.5, 129.2, 129.8,
130.3, 131.7, 133.0 (aromatic carbons)
M+.(+ve scan) 488.3
0
9H, C4 -H and Ar-H), 10.07 (bs, 1H,
NH-SO2)
18c
5.05 (s, 2H, CH2-(C-5)), 5.27 (s, 2H,
CH2-(C-2)), 6.64 (bs, 1H, NH), 7.21–
50.7 (CH2-(C-5)), 52.9 (CH2-(C-2)), 135.3 (C-40), 139.7
M++2 (+ve scan)
(C-50), 146.7 (C-30), 159.6 (C-5), 161.7 (C-2), 125.4, 126.8, 531.1
127.5, 128.2, 128.7, 129.6, 131.4, 134.2 (aromatic carbons)
(Continued)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2013
Synthesis of a New Class of Sulfonamido Bis Heterocycles
Table 3
(Continued)
Compound
19a
1H NMR (CDCl3/DMSO-d6) d, (ppm)
13C NMR (CDCl3/DMSO-d6) d, (ppm)
MS (m/z)
0
7.82 (m, 9H, C4 -H and Ar-H), 10.17 (bs,
1H, NH-SO2)
5.01 (s, 2H, CH2-(C-5)), 5.19 (s, 2H,
CH2-(C-2)), 6.60 (bs, 1H, NH),
51.3 (CH2-(C-5)), 53.1 (CH2-(C-2)), 135.7 (C-40), 139.4
(C-50), 146.3 (C-30), 158.4 (C-5), 160.6 (C-2), 127.2, 128.3,
128.9, 129.7, 130.6, 132.4, 133.4, 134.8 (aromatic carbons)
M+. 475
0
7.24–7.91 (m, 11H, C4 -H and Ar-H),
10.16 (bs, 1H, NH-SO2)
19b
2.26 and 2.35 (s, 6H, Ar-CH3), 5.08 (s,
2H, CH2-(C-5)), 5.23 (s, 2H, CH2-(C-
2)), 6.63 (bs, 1H, NH), 7.16–7.83 (m,
21.4 and 22.0 (Ar-CH3), 50.9 (CH2-(C-5)), 52.7 (CH2-(C-
2)), 135.5 (C-40), 139.0 (C-50), 145.9 (C-30), 158.2 (C-5),
160.3 (C-2), 126.7, 127.3, 128.1, 128.8, 129.4, 130.5,
131.6, 133.7 (aromatic carbons)
M+.(+ve scan) 504.5
0
9H, C4 -H and Ar-H), 10.19 (bs, 1H,
NH-SO2)
19c
20a
20b
5.10 (s, 2H, CH2-(C-5)), 5.36 (s, 2H,
CH2-(C-2)), 6.76 (bs, 1H, NH), 7.19–
7.86 (m, 9H, C4 -H and Ar-H), 10.26
51.5 (CH2-(C-5)), 53.5 (CH2-(C-2)), 136.0 (C-40), 140.1
M++2 (+ve scan)
(C-50), 147.3 (C-30), 159.2 (C-5), 161.1 (C-2), 125.5, 126.2, 547.1
127.1, 127.7, 129.3, 130.6, 132.4, 134.6 (aromatic carbons)
0
(bs, 1H, NH-SO2)
5.12 (s, 2H, CH2-(C-5)), 5.28 (s, 2H,
CH2-(C-3)), 5.76 (bs, 2H, NH2), 6.72
(bs, 1H, NH), 7.11–7.76 (m, 11H, C4 -H 127.5, 128.1, 128.8, 129.5, 131.3, 133.9 (aromatic carbons)
and Ar-H), 10.21 (bs, 1H, NH-SO2)
2.25 and 2.33 (s, 6H, Ar-CH3), 5.07
(s, 2H, CH2-(C-5)), 5.21 (s, 2H, CH2-
50.4 (CH2-(C-5)), 53.1 (CH2-(C-3)), 135.8 (C-40), 139.7
(C-50), 146.8 (C-30), 159.0 (C-5), 160.7 (C-3), 125.6, 126.7,
M+. 473
0
21.5 and 22.3 (Ar-CH3), 49.8 (CH2-(C-5)), 53.0 (CH2-
(C-3)), 135.3 (C-40), 140.4 (C-50), 147.1 (C-30), 158.8 (C-5),
M+.(+ve scan) 502.2
(C-3)), 5.69 (bs, 2H, NH2), 06.68 (bs, 1H, 160.6 (C-3), 126.7, 127.5, 128.4, 129.5, 130.2, 130.8,
NH), 7.18–7.80 (m, 9H, C4 -H and
Ar-H), 10.17 (bs, 1H, NH-SO2)
5.17 (s, 2H, CH2-(C-5)), 5.41 (s, 2H,
CH2-(C-3)), 5.78 (bs, 2H, NH2), 6.709
(bs, 1H, NH), 7.29–7.87 (m, 9H, C4 -H
and Ar-H), 10.35 (bs, 1H, NH-SO2)
132.4, 133.7 (aromatic carbons)
20c
51.1 (CH2-(C-5)), 53.7 (CH2-(C-3)), 136.6 (C-40), 141.2
M++2 (+ve scan)
(C-50), 148.0 (C-30), 159.7 (C-5), 161.8 (C-3), 125.8, 126.4, 545.2
127.4, 127.9, 129.5, 130.7, 131.3, 135.6 (aromatic carbons)
Arylaminosulfonylacetic acid hydrazide (1): general procedure.
The compound methyl arylaminosulfonylacetate [25] (10 mmol),
hydrazine hydrate (11 mmol), methanol (6 mL), and three drops
of pyridine were refluxed for 7–9 h. The reaction mixture was
cooled and the solid separated was collected by filtration, dried,
and recrystallized from methanol.
with concentrated HCl to pH ꢀ 3 and washed with water, dried,
and recrystallized from ethanol.
2-(Arylaminosulfonylmethyl)-5-(30-aroyl-10H-pyrrol-40-ylsulfonyl
methyl)-1,3,4-oxadiazole (6), 2-(arylaminosulfonylmethyl)-5-(30-
aroyl-10H-pyrrol-40-ylsulfonylmethyl)-1,3,4-thiadiazole (7), and
4-amino-3-(arylaminosulfonylmethyl)-5-(30-aroyl-10H-pyrrol-40-
2-(Arylaminosulfonylmethyl)-5-[E-(2-aroylvinylsulfonylmethyl)]-
1,3,4-oxadiazole (3): general procedure. To an equimolar mixture
(10 mmol) of arylaminosulfonylacetic acid hydrazide (1) and
aroylethenesulfonylacetic acid (2), POCl3 (7 mL) was added and
heated under reflux for 6–8 h. The excess POCl3 was removed
under reduced pressure, and the residue was poured onto crushed
ice. The solid separated was filtered on Buchner funnel. It was
washed with saturated sodium bicarbonate solution, followed by
water, dried, and recrystallized from ethanol.
2-(Arylaminosulfonylmethyl)-5-[E-(2-aroylvinylsulfonylmethyl)]-
1,3,4-thiadiazole (4): general procedure. The compound 3 (5 mmol),
thiourea (20 mmol), and tetrahydrofuran (5 mL) were taken in
a sealed test tube and heated at 120–150ꢂC in an oil bath for
20–23 h. After the reaction was completed, it was extracted
with dichloromethane. The organic layer was washed with
water, brine solution, and dried over anhydrous Na2SO4. The
solvent was removed under vacuum, and the resultant solid
was recrystallized from methanol.
ylsulfonylmethyl)-1,2,4-triazole (8): general procedure.
To a
suspension of NaH (50 mg) in Et2O (10mL) at room temperature,
the compounds 3, 4, and 5 (1 mmol) and TosMIC (2 mmol) in
Et2O-DMSO (2 : 1) was added dropwise while stirring and stirring
was continued for 4–6 h. Then, water was added and the reaction
mass was extracted with ether. The ethereal layer was dried over
anhydrous Na2SO4 and filtered. The solvent was removed under
reduced pressure, and the resultant residue was purified by column
chromatography using silica gel (hexane–ethyl acetate; 4 : 1).
2-(Arylaminosulfonylmethyl)-5-(30-aroyl-40,50-dihydro-10H-pyrazol-
40-ylsulfonyl-methyl)-1,3,4-oxadiazole (9), 2-(arylaminosulfonylmethyl)-
0
0
0
0
0
5-(3 -aroyl-4 ,5 -dihydro-1 H-pyrazol-4 -ylsulfonylmethyl)-1,3,4-thiadiazole
(10), and 4-amino-3-(arylaminosulfonyl-methyl)-5-(30-aroyl-40,50-
dihydro-10H-pyrazol-40-ylsulfonylmethyl)-1,2,4-triazole (11): general
procedure. To a well-cooled solution of compounds 3, 4, and 5
(5mmol) in dichloromethane (20 mL), an ethereal solution of
diazomethane (40 mL, 0.4M) and triethylamine (0.12 g) was
added. The reaction mixture was kept at ꢁ20 to ꢁ15ꢂC for 48h.
Evaporation of the solvent in vacuo furnished a crude product,
which was purified by passing through a column of silica gel
using hexane and ethyl acetate (3 : 1) as eluent.
4-Amino-3-(arylaminosulfonylmethyl)-5-E-(2-aroylvinylsulfonyl
\methyl)-1,2,4-triazole (5): general procedure.
A mixture of 3
(5 mmol), hydrazine hydrate (15 mmol), and n-butanol (25 mL) was
refluxed for 5–7 h. To this, KOH (10 mmol) was added, and the
precipitate formed was filtered. The solid obtained was acidified
2-(Arylaminosulfonylmethyl)-5-(30-aryl-40,50-dihydro-10H-pyrazol-
50-ylsulfonyl-methyl)-1,3,4-oxadiazole (12), 2-(arylaminosulfonylmethyl)-
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

A. Muralikrishna, G. Mallikarjuna Reddy, G. Lavanya, V. Padmavathi, and A. Padmaja
Vol 000
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[4] Padmavathi, V.; Jagan Mohan Reddy, B.; Rajagopala Sharma,
M.; Thriveni, P. J Chem Res (S) 2004, 1, 79.
[5] Dannahardt, G.; Kiefer, W.; Kramer, G.; Maehrlein, S.; Nowe,
U.; Fiebich, B. Eur J Med Chem 2000, 35, 499.
[6] Lee, A. G. Synthesis 1982, 6, 508.
[7] Zarudnitskii, E. V.; Pervak, I. I.; Merkulov, A. S.; Yurchenko,
A. A.; Tolmachev, A. A. Tetrahedron 2008, 64, 10431 and references
cited therein.
5-(3 -aryl-4 ,5 -dihydro-1 H-pyrazol-5 -ylsulfonylmethyl)-1,3,4-thiadiazole
(13), and 4-amino-3-(arylaminosulfonylmethyl)-5-(30-aryl-40,50-dihydro-
10H-pyrazol-50-ylsulfonylmethyl)-1,2,4-triazole (14): general procedure.
To a solution of 3, 4, and 5 (2.5 mmol) in methanol (15 mL), hydrazine
hydrate (5 mmol) was added and refluxed for 6–8 h and cooled. The
solid obtained was filtered and dried. It was purified by column
chromatography (silica gel, hexane–ethyl acetate, 3 : 1).
2-(Arylaminosulfonylmethyl)-5-(30-aroyl-10H-pyrazol-40-ylsulfonyl
methyl)-1,3,4-oxadiazole (15), 2-(arylaminosulfonylmethyl)-5-(30-
aroyl-10H-pyrazol-40-ylsulfonylmethyl)-1,3,4-thiadiazole (16),
4-amino-3-(arylaminosulfonylmethyl)-5-(30-aroyl-10H-pyrazol-40-
ylsulfonylmethyl)-1,2,4-triazole (17), 2-(arylaminosulfonylmethyl)-
5-(30-aryl-10H-pyrazol-50-ylsulfonylmethyl)-1,3,4-oxadiazole (18),
[8] Jin, G. Y.; Hou, Z.; Zhao, G. F.; Cao, C. Y.; Li, Y. C. Chem J
Chin Univ 1997, 18, 409.
[9] Lu, S. M.; Chen, R. Y. Org Prep Proced Int 2000, 32, 302.
[10] Hui, X. P.; Zhang, L. M.; Zhang, Z. Y.; Wang, Q.; Wang, F.
Indian J Chem 1999, 38B, 1066.
[11] Griffin, D. A.; Mannion, S. K. Eur Pat Appl Ep 1986, 474,
199; Chem Abstr 1987, 106, 98120u.
[12] Hussain, M. I.; Amir, M. J Indian Chem Soc 1986, 63, 317.
[13] Chiu, S. H. L.; Huskey, S. E. W. Drug Metabol Dispos 1998,
26, 838.
[14] Emilsson, H.; Salender, H.; Gaarder, J. Eur J Med Chem Chim
Ther 1985, 21, 333.
[15] Demirbas, N.; Ugurluoglu, R.; Demirbas, A. Bioorg Med
Chem 2002, 10, 3717.
[16] Turan-Zitouni, G.; Kaplancikli, Z. A.; Erol, K.; Kiliç, F. S.
Farmaco 1999, 54, 218.
[17] Padmavathi, V.; Sudhakar Reddy, G.; Dinneswara Reddy, G.;
Payani T. Synth Commun 2010, 40, 482.
2-(arylaminosulfonylmethyl)-5-(3 -aryl-1 H-pyrazol-50-ylsulfonylmethyl)-
1,3,4-thiadiazole (19), and 4-amino-3-(arylaminosulfonylmethyl)-
5-(30-aryl-10H-pyrazol-50-ylsulfonylmethyl)-1,2,4-triazole (20): general
procedure. The compounds 9, 10, 11, 12, 13, and 14 (1 mmol),
chloranil (1.1 mmol), and xylene (10 mL) were refluxed for 22–26 h.
The reaction mixture was treated with a 5% NaOH solution. The
organic layer was separated and repeatedly washed with water. It
was dried over anhydrous Na2SO4 and the solvent was removed
under reduced pressure. The resultant solid was recrystallized
from methanol.
0
0
[18] Bordner, C. A. US Patent 2600, 1952, 689; Chem Abstr 1953,
47, 4373.
Acknowledgments. The authors thank the Council of Scientific
and Industrial Research (CSIR), New Delhi for financial assistance
under major research project.
[19] Van Tamelen, E. E. J Am Chem Soc 1951, 73, 3444.
[20] Price, C. C.; Kirk, P. F. J Am Chem Soc 1953, 75, 2396.
[21] Culvenor, C. C.; Davies, W.; Savige, W. E. J Chem. Soc.,
1952, 4480–4486.
[22] Linganna, N.; Lokanatha Rai, K. M. Synth Commun 1998, 28,
4611.
[23] Kiyoshi, F.; Senji, T. Chem Pharm Bull 1960, 8, 908.
[24] Padmavathi, V.; Mahesh, K.; Subbaiah, D. R. C. V.; Deepti,
D.; Sudhakar Reddy, G. Arkivoc 2009, X, 195.
[25] Padmavathi, V.; Nagi Reddy, S.; Dinneswara Reddy, G.;
Padmaja, A. Eur J Med Chem 2010, 45, 4246.
REFERENCES AND NOTES
[1] Wemmer, D. E. Biopolymers 2001, 52, 197.
[2] Liu, J. H.; Chan, H. W.; Wong, H. N. C. J Org Chem 2000, 65, 3274.
[3] Pavri, N. P.; Trudell, M. L. J Org Chem 1997, 62, 2649
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet