Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides

Article abstract of DOI:10.1002/jhet.3634

A new class of benzazolyl azolyl sulfamoyl acetamides was prepared from azolyl sulfamoyl acetates and benzazolyl amines in the presence of KO^tBu in tetrahydrofuran. Compounds with benzothiazole-thiazole, benzimidazole-thiazole, benzothiazole-imidazole, and benzimidazole-imidazole moieties exhibited excellent antibacterial activity against Bacillus subtilis.

Full text of DOI:10.1002/jhet.3634

Month 2019
Synthesis and Antibacterial Activity of Benzazolyl Azolyl
Sulfamoyl Acetamides
Tankam Rajeswari,a Tamatam Rekha,a Guda Dinneswara Reddy,b Adivireddy Padmaja,a
and
a
*
Venkatapuram Padmavathi
aDepartment of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh, India
bDepartment of Korea Center for Artificial Photosynthesis and Center for Nano-Materials, Sogang University, Mapo-gu,
Seoul 121-742, South Korea
*E-mail: vkpuram2001@yahoo.com
Received March 31, 2019
DOI 10.1002/jhet.3634
Published online 00 Month 2019 in Wiley Online Library (wileyonlinelibrary.com).
A new class of benzazolyl azolyl sulfamoyl acetamides was prepared from azolyl sulfamoyl acetates and
benzazolyl amines in the presence of KOtBu in tetrahydrofuran. Compounds with benzothiazole-thiazole,
benzimidazole-thiazole, benzothiazole-imidazole, and benzimidazole-imidazole moieties exhibited excellent
antibacterial activity against Bacillus subtilis.
J. Heterocyclic Chem., 00, 00 (2019).
INTRODUCTION
dine [28], O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethy
luronium hexaflourophosphate/diisopropylethylamine
The amide/sulfonamide bond is a vital component of
biomolecules and is one of the most important functional
groups because many natural products, medicinal and
functional materials contain this moiety. The
comprehensive medicinal chemistry database revealed that
carboxamide group appears in more than 25% of known
drugs [1] because they are neutral and stable and have
both hydrogen bond accepting and donating properties [2].
Sulfonamides as artificial antifolic agents have been
widely used for the prevention and cure of bacterial
infections and have evoked high favor in medicinal
chemistry because of their diverse activities including
antibacterial [3], antifungal [4], antiviral [5], antitumour
[6], and anti-inflammatory [7]. Further, azoles and
benzazoles are prevalent scaffolds in pharmaceutical
industry with wide range of applications in drug discovery
as anticancer [8–10], anti-HIV [11,12], antioxidant [13],
antitumour [14–17], and antimicrobial [18–21] agents. It is
well known that the combination of two or more
heterocycles in one molecule could yield a novel entity
with enhanced biopotency. Moreover, combination of
sulfonamide and amide moieties with potential
heterocycles is being used to develop novel formulations.
Functionalization of acid and their derivatives with amines
is one of the most widely used methods for amide
synthesis either by direct reaction of an amine with an acid
or by reaction of acid derivatives with an amine in the
presence of zinc acetate [22], brine [23], copper oxide
(DIPEA) [29], 1-ethyl-3-(3-dimethylaminopropyl)carbo
diimide /DIPEA [29], O-(benzotriazol-1-yl)-N,N,N′,N′-
tetramethyluronium tetrafluoroborate/DIPEA,[30] and 1-
ethyl-3-(3-dimethylaminopropyl)carbodiimide/dimethy
laminopyridine [31] for the development of amide group. In
continuation of our efforts to synthesize, a variety of
molecules benzazolyl azolyl sulfamoyl acetamides as
effective antibacterial agents have been taken up.
RESULTS AND DISCUSSION
Chemistry. The azolyl amines—4-thiophenyloxazolyl-
2-amine (1) and 4-thiophenylthiazolyl-2-amine (2)—were
prepared by the condensation of 2-bromo-1-(thiophen-2-
yl)ethan-1-one with urea and thiourea in methanol [32].
4-Thiophenylimidazolyl-2-amine (3) was prepared by the
hydrolysis of N-4-thiophenyl-1H-imidazol-2-ylacetamide
in the presence of H2SO4. The latter compound was
obtained by the treatment of 2-bromo-1-(thiophen-2-yl)
ethan-1-one with acetylguanidine [33]. The sufonylation
of heteroarylamines was reported by several methods
[28,34]. Recently, we have reported N-sulfonylation
reaction in the presence of dispersed sodium where in the
reaction proceeded at a faster rate with high yields [35].
In fact, the reaction of 1 with methyl 2-(chlorosulfonyl)
acetate (4) in the presence of dispersed sodium under
ultrasonication gave methyl 2-(N-(4-(4-thiophen-2-yl)
oxazol-2-yl)sulfamoyl)acetate (5) in excellent yield.
Adopting similar methodology, methyl 2-(N-(4-(4-
[24],
N,N,N′,N′-tetramethylethylenediamine
[25],
aluminium [26], triethylamine [27], etc. In fact, we have
adopted dicyclohexylcarbodiimide/4-dimethylaminopyri
thiophen-2-yl)thiazol-2-yl)sulfamoyl)acetate
(6)
and
© 2019 Wiley Periodicals, Inc.

T. Rajeswari, T. Rekha, G. Dinneswara Reddy, A. Padmaja, and V. Padmavathi
Vol 000
methyl
2-(N-(4-(4-thiophen-2-yl)-1H-imidazol-2-yl)
thiophen-2-yl)oxazol-2-yl)sulfamoyl)acetamide (12) and
N-(1H-benzimidazol-2-yl)-2-(N-(4-(4-thiophen-2-yl)
sulfamoyl)acetate (7) were prepared from 2 and 3 on
reaction with 4 (Scheme 1). The dispersed sodium may
react with 4 by a single electron transfer to give methyl
2-sulfonylacetate free radical and sodium chloride. The
sulfonylacetate free radical reacts with amines 4-
thiophenyloxazolyl-2-amine to obtain sulfonamide by the
oxazol-2-yl)sulfamoyl)acetamide (13). The 1H NMR
spectra of 11a, 12a, and 13a displayed a singlet at δ 4.20,
4.24, and 4.23 because of methylene protons and two
broad singles at 10.42, 10.39, 10.22 and 10.49, 12.41,
10.42 ppm because of NH of sulfonamide and amide
groups. The reaction of 6 was also carried out with 8/9/
10 in the presence of potassium tert-butoxide to obtain
N-(benzoxazol-2-yl)-2-(N-(4-(4-thiophen-2-yl)thiazol-2-
yl)sulfamoyl)acetamide (14), N-(benzothiazol-2-yl)-2-(N-
(4-(4-thiophen-2-yl)thiazol-2-yl)sulfamoyl)acetamide
(15), and N-(1H-benzimidazol-2-yl)-2-(N-(4-(4-thiophen-
2-yl)thiazol-2-yl)sulfamoyl)acetamide (16). The 1H
NMR spectra of 14a, 15a, and 16a showed a singlet at
δ 4.25, 4.22, and 4.24 because of methylene protons
and two broad singles at 10.52, 10.46, 10.26 and
10.54, 12.43, 10.52 ppm because of NH of sulfonamide
and amide groups. N-(Benzoxazol-2-yl)-2-(N-(4-(4-
thiophen-2-yl)-1H-imidazol-2-yl)sulfamoyl)acetamide
(17), N-(benzothiazol-2-yl)-2-(N-(4-(4-thiophen-2-yl)-1H-
imidazol-2-yl)sulfamoyl)acetamide (18), and N-(1H-
benzimidazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-yl)-1H-
imidazol-2-yl)sulfamoyl)-acetamide (19) were prepared
1
expulsion of H• (mechanism). The H NMR spectra of
5a, 6a, and 7a showed two singlets at δ 3.68, 3.70, 3.69
and 4.36, 4.32, 4.31 because of OMe and CH2 protons.
In addition, a broad singlet was observed at 10.46 in 5a,
at 10.44 in 6a, and at 10.38 in 7a because of sulfonamide
NH. Compound 7a showed another broad singlet at
12.88 ppm because of NH of imidazole. The signals of
NH disappeared when D2O was added. Benzoxazol-2-
amine (8), benzothiazol-2-amine (9), and 1H-
benzimidazol-2-amine (10) were prepared by the
cyclocondensation of 2-aminophenol, 2-aminothiophenol,
and 1,2-phenylenediamine with cyanogen bromide in
methanol [36,37]. The reaction of 5 with 8 in the
presence of potassium tert-butoxide in tetrahydrofuran
resulted in N-(benzoxazol-2-yl)-2-(N-(4-(4-thiophen-2-yl)
oxazol-2-yl)sulfamoyl)acetamide (11). Similar reaction of
5 with 9 and 10 gave N-(benzothiazol-2-yl)-2-(N-(4-(4-
Scheme 1
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Month 2019
Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides
by the treatment of
7
with 8/9/10, respectively
10.49, 10.23 and 10.54, 12.42, 10.47 ppm because of
NH of sulfonamide and amide groups. The signals of
highly acidic protons in these compounds disappeared
on deuteration.
(Scheme 2). The 1H NMR spectra of 17a, 18a, and
19a showed a singlet at δ 4.21, 4.23, and 4.23 because
of methylene protons and two broad singles at 10.50,
Scheme 2
S. no.
1
Ester
Amine
Product
8
9
5
11a
12a
13a
14a
2
3
4
5
5
10
8
6
5
6
9
15a
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T. Rajeswari, T. Rekha, G. Dinneswara Reddy, A. Padmaja, and V. Padmavathi
Vol 000
S. no.
6
Ester
Amine
Product
6
10
16a
17a
18a
19a
7
8
9
8
7
7
9
7
10
11a–19a R =Cl.
11b–19b R =NO2.
Antibacterial activity.
The results of antibacterial
exhibited moderate activity. The results also revealed that
the activity increased with increasing electronegativity of
the substituents. In fact, nitro-substituted compounds
showed higher activity than chloro-substituted ones in the
respective series.
activity shown in Table 1 and Figure 1 indicated that
Gram-positive bacteria were more susceptible towards the
tested compounds than Gram-negative bacteria.
Compounds having either thiazole or benzothiazole
moieties displayed excellent activity particularly against
Bacillus subtilis. In fact, compounds having
benzothiazole-thiazole (15), benzimidazole-thiazole (16),
and benzothiazole-imidazole (18) showed excellent
antibacterial activity against B. subtilis higher than the
standard drug Chloramphenicol at the tested
concentrations. However, nitro-substituted benzimidazole-
imidazole (19) showed equal activity to the standard
drug. Further, it was observed that 15 displayed greater
activity than 16 and 18. Among the latter compounds, 16
showed slightly higher activity than 18. However,
compounds having benzoxazole in combination with
oxazole (11) and imidazole (17) showed least activity
whereas benzothiazole with oxazole (12), benzimidazole
with oxazole (13), and benzoxazole with thiazole (14)
Minimum inhibitory concentration/minimum bactericidal
concentration of compounds 15a, 15b, 16a, 16b, 18a, 18b,
and 19b.
The compounds that showed higher
antibacterial activity were further assayed for minimum
inhibitory concentration (MIC) and minimum bactericidal
concentration (MBC), and the results are presented in
Table 2. MIC is the lowest concentration of an
antimicrobial that will inhibit the visible growth of a
microorganism. (But it is not sure that the
microorganisms are completely killed.) The MBC is the
lowest concentration of antibiotic required to kill a
particular bacterium. The MBC involves an additional set
of steps performed when once MIC is determined. The
antimicrobials are usually regarded as bactericidal if the
MBC is not greater than four times the MIC [38]. MIC
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2019
Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides
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DOI 10.1002/jhet

T. Rajeswari, T. Rekha, G. Dinneswara Reddy, A. Padmaja, and V. Padmavathi
Vol 000
Figure 1. The in vitro antibacterial activity of compounds 11–19. [Color figure can be viewed at wileyonlinelibrary.com]
Table 2
MIC/MBC of compounds 15a, 15b, 16a, 16b, 18a, 18b, and 19b.
MIC
MIC/MBC (μg/well)
Compound
S. aureus
B. subtilis
P. aeruginosa
K. pneumoniae
15a
15b
16a
16b
18a
18b
19b
25 (100)
25 (100)
50 (200)
25 (100)
50 (200)
50 (200)
50 (200)
12.5
6.25 (12.5)
6.25 (12.5)
6.25 (12.5)
6.25 (12.5)
6.25 (12.5)
6.25 (12.5)
6.25 (12.5)
6.25
50 (200)
50 (200)
100 (>200)
50 (200)
100 (>200)
100 (>200)
100 (>200)
6.25
50 (200)
50 (200)
100 (>200)
100 (>200)
200 (—)
200 (—)
200 (—)
6.25
Chloramphenicol
Ketoconazole
—
—
—
—
MBC, minimum bactericidal concentration; MIC, minimum inhibitory concentration.
À, no activity; , standard deviation.
values of compounds 15a, 15b, 16a, 16b, 18a, 18b, and
19b against B. subtilis are equal to standard drug
Chloramphenicol, and MBC value is 2 × MIC. This
indicated that 15a, 15b, 16a, 16b, 18a, 18b, and 19b are
potential antibacterial agents against B. subtilis. The
structure–activity relationship of the compounds revealed
that nitro-substituted benzothiazole-thiazole (15b),
benzimidazole-thiazole (16b), and benzothiazole-
imidazole (18b) displayed prominent antibacterial activity
than the corresponding chloro-substituted compounds
(15a, 16a, and 18a). The activity increased with
increasing electronegativity.
benzazolyl amines in the presence of KOtBu in
tetrahydrofuran. Compounds having thiazole and
benzothiazole moieties displayed excellent activity
particularly against B. subtilis. In fact, benzothiazole-
thiazole, benzimidazole-thiazole, and benzothiazole-
imidazole containing compounds exhibited excellent
antibacterial activity against B. subtilis greater than the
standard drug Chloramphenicol. Further, nitro-substituted
compounds in each series exhibited greater activity than
chloro-substituted ones.
EXPERIMENTAL
General.
Melting points were determined in open
CONCLUSION
capillaries on a Mel-Temp apparatus (FTIR spectrometer,
Thermo Electron Scientific Instruments LLC, Madison,
WI) and are uncorrected. The purity of the compounds
A new class of benzazolyl azolyl sulfamoyl acetamides
was prepared from azolyl sulfamoyl acetates and
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2019
Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides
was checked by thin-layer chromatography (silica gel H,
BDH, hexane/ethyl acetate, 3:1). The IR spectra were
recorded on a Thermo Nicolet IR 200 FTIR spectrometer
(Darmstadt, Germany) as KBr pellets, and the wave num-
concentration that inhibited visible growth of the tested
organisms.
To determine the MBC [41] for each set of test tubes in
the MIC determination, a loopful of broth was collected
from those tubes that did not show any growth and
inoculated on sterile NB by streaking. These inoculated
plates were incubated at 37°C for 24 h. After incubation,
the lowest concentration was noted as MBC at which no
visible growth was observed.
bers were given in cmÀ1
.
1
The H NMR and 13C NMR spectra were recorded in
hexadeuterated dimethyl sulfoxide (DMSO-d6) on a
Bruker spectrometer (Germany) operating at 400 and
100 MHz. All chemical shifts are reported in δ (ppm) using
tetramethylsilane as an internal standard. High-resolution
mass spectra were recorded on Micromass Q-TOF spec-
trometer (Woburn, MA) using electrospray ionization.
The progress of the reaction is monitored by thin-layer
chromatography using silica gel plates (silica gel 60
F254-0.25 mm), and components are visualized by obser-
vation under UV light (254 and 365 nm). The synthetic in-
General procedure for the synthesis of methyl
4-thiophenylazolylsulfamoylacetate (5/6/7). A mixture of
methyl 2-chlorosulfonylacetate (4) (0.001 mol), dispersed
sodium (0.0414 g, 1.8 mg atom), and tetrahydrofuran
(3 mL) was sonicated for 8 min in a sonic bath at a
frequency of 46 KHz at 25°C. To this, azolyl-2-amine (1/
2/3) was added and continued sonication for 12–16 min.
After completion of the reaction (monitored by thin-layer
chromatography), the organic matter was filtered, washed
with water, extracted with ether, and dried. Removal of
the solvent under reduced pressure gave a solid that was
recrystallized from ethanol.
termediates
4-thiophenyloxazolyl-2-amine
(1),
thiophenylthiazolyl-2-amine (2), 4-thiophenylimidazolyl-
2-amine (3), benzoxazol-2-amine (8), benzothiazol-2-
amine (9), and 1H-benzimidazole-2-amine (10) were pre-
pared as per the literature procedures [32–34].
Biological activity assays.
The in vitro antibacterial
Methyl
2-(N-(4-(4-chlorothiophen-2-yl)oxazol-2-yl)sulfa
activity was studied by agar well diffusion method against
test organisms [39]. Nutrient broth (NB) plates were
swabbed with 24 h old broth culture (100 μL) of test
bacteria. Wells (6 mm) were made into each petri plate
using the sterile cork borer. The compounds were
dissolved in DMSO of 5 mg/mL, and from this, 25, 50,
and 100 μg/well were added into the wells by using sterile
pipettes. Simultaneously, standard antibiotic (positive
control) for antibacterial activity, Chloramphenicol, was
tested against the pathogens. The samples were dissolved
in DMSO (negative control) that showed no zone of
inhibition. The plates were incubated at the temperature of
37°C for 24 h. After incubation, diameter of zone of
inhibition of each well was measured. Duplicates were
carried out, and the average values were calculated for
antibacterial activity.
Broth dilution test was used to determine MIC of the
aforementioned samples [40]. Freshly prepared NB was
used as diluents. The 24 h old culture of the test bacteria
Staphylococcus aureus, B. subtilis, Pseudomonas
aeruginosa, and Klebsiella pneumoniae was diluted 100-
folds in NB (100 μL bacterial cultures in 10 mL NB).
The stock solution of the compounds was prepared in
DMSO by dissolving 5 mg of the compound in 1 mL of
DMSO. Increasing concentrations of the test samples (5,
10, and 20 μL of stock solution contains 25, 50, and
100 μg of the compounds) were added to the test tubes
containing the bacterial cultures. All the tubes were
incubated at 37°C for 24 h. The tubes were examined for
visible turbidity using NB as control. Simultaneously,
control without test samples and with solvent was
assayed. The MIC was recorded as the lowest
moyl)acetate (5a).
Yield 75%; mp: 122–124°C; IR
(KBr): 1129, 1327 (SO2), 1579 (C═N), 1632 (C═C),
1680 (C═O), 3356 (NH) cmÀ1 1H NMR (400 MHz,
;
DMSO-d6): δ 3.68 (s, 3H, O–CH3), 4.36 (s, 2H, CH2),
7.07 (s, 1H, C5′–H), 7.35 (s, 1H, C3′–H), 7.58 (s, 1H,
C5–H), 10.46 (bs, 1H, SO2NH) ppm; 13C NMR
(100 MHz, DMSO-d6): δ 49.1 (O–CH3), 70.4 (CH2),
118.9 (C-5′), 123.7 (C-3′), 125.4 (C-4), 127.2 (C-4′),
141.5 (C-5), 145.1 (C-2′), 146.6 (C-2), 163.0 (C═O)
ppm; HRMS (m/z): 359.7513 [M+Na]; Anal. Calcd. for
C10H9ClN2O5S2: C, 35.67; H, 2.69; N, 8.32; Found: C,
35.74; H, 2.63; N, 8.41%.
Methyl 2-(N-(4-(4-nitrothiophen-2-yl)oxazol-2-yl)sulfamoyl)
acetate (5b).
Yield 72%; mp: 145–147°C; IR (KBr):
1135, 1321 (SO2), 1587 (C═N), 1650 (C═C), 1676
(C═O), 3367 (NH) cmÀ1 1H NMR (400 MHz,
;
DMSO-d6): δ 3.64 (s, 3H, O–CH3), 4.34 (s, 2H, CH2),
7.61 (s, 1H, C5–H), 8.39 (s, 1H, C5′–H), 8.66 (s, 1H,
C3′–H), 10.48 (bs, 1H, SO2NH) ppm; 13C NMR
(100 MHz, DMSO-d6): δ 51.9 (O–CH3), 65.6 (CH2),
117.3 (C-3′), 127.1 (C-4), 132.6 (C-5′), 138.0 (C-5),
146.5 (C-2′), 149.4 (C-4′), 153.2 (C-2), 162.8 (C═O)
ppm; HRMS (m/z): 370.3051 [M+Na]; Anal. Calcd. for
C10H9N3O7S2: C, 34.58; H, 2.61; N, 12.10; Found: C,
34.50; H, 2.66; N, 12.26%.
Methyl
2-(N-(4-(4-chlorothiophen-2-yl)thiazol-2-yl)sulfa
moyl)acetate (6a).
Yield 76%; mp: 138–140°C; IR
(KBr): 1143, 1335 (SO2), 1583 (C═N), 1643 (C═C),
1688 (C═O), 3365 (NH) cmÀ1 1H NMR (400 MHz,
;
DMSO-d6): δ 3.70 (s, 3H, O–CH3), 4.32 (s, 2H, CH2),
7.02 (s, 1H, C5–H), 7.10 (s, 1H, C5′–H), 7.41 (s, 1H,
C3′–H), 10.44 (bs, 1H, SO2NH) ppm; 13C NMR
(100 MHz, DMSO-d6): δ 49.7 (O–CH3), 63.2 (CH2),
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T. Rajeswari, T. Rekha, G. Dinneswara Reddy, A. Padmaja, and V. Padmavathi
Vol 000
106.2 (C-5), 124.3 (C-5′), 127.0 (C-3′), 131.5 (C-4′),
140.3 (C-4), 145.1 (C-2′), 162.6 (C═O), 165.4 (C-2)
ppm; HRMS (m/z): 375.8122 [M+Na]; Anal. Calcd. for
C10H9ClN2O4S3: C, 34.04; H, 2.57; N, 7.94; Found: C,
33.98; H, 2.62; N, 7.99%.
Methyl 2-(N-(4-(4-nitrothiophen-2-yl)thiazol-2-yl)sulfamoyl)
cloth. The stopper was then held firmly and shaken
vigorously for 2–3 min until the molten sodium was
converted into a fine dispersion. Immediately, the stopper
was removed, and the flask was placed on the cork ring.
The sodium was obtained in the form of small spheres
depending upon the time and rapidity of shaking. Then
the contents were cooled to room temperature, the xylene
was decanted, and the sodium was washed with sodium-
dried ether. The dispersed sodium as small spheres was
preserved in absolute ether.
acetate (6b).
Yield 74%; mp: 163–165°C; IR (KBr):
1124, 1341 (SO2), 1578 (C═N), 1652 (C═C), 1674
(C═O), 3371 (NH) cmÀ1 1H NMR (400 MHz,
;
DMSO-d6): δ 3.74 (s, 3H, O–CH3), 4.36 (s, 2H, CH2),
7.05 (s, 1H, C5–H), 8.35 (s, 1H, C5′–H), 8.69 (s, 1H,
C3′–H), 10.42 (bs, 1H, SO2NH) ppm; 13C NMR
(100 MHz, DMSO-d6): δ 50.2 (O–CH3), 64.5 (CH2),
109.7 (C-5), 121.2 (C-3′), 128.7 (C-5′), 144.5 (C-4),
146.4 (C-2′), 152.3 (C-4′), 162.1 (C═O), 169.6 (C-2)
ppm; HRMS (m/z): 386.3673 [M+Na]; Anal. Calcd. for
C10H9N3O6S3: C, 33.05; H, 2.50; N, 11.56; Found: C,
33.12; H, 2.54; N, 11.65%.
General procedure for the synthesis of N-benzazolyl-4-
thiophenylazolylsulfamoylacetamide (11–19).
A mixture
of potassium tert-butoxide (0.0011 mol) and tetrahy
drofuran (5 mL) was sonicated at room temperature for
5 min. To this, methyl (azolyl-2-ylsulfomoyl)acetate (5/6/
7) (0.001 mol) and benzazolyl-2-amine (8/9/10) were
added and continued sonication at room temperature for
15–25 min. The solvent was evaporated under reduced
pressure. The gummy substance was recrystallized from
ethanol.
Methyl
2-(N-(4-(4-chlorothiophen-2-yl)-1H-imidazol-2-yl)
sulfamoyl)acetate (7a). Yield 77%; mp: 149–151°C; IR
N-(Benzo[d]oxazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-yl)
(KBr): 1148, 1330 (SO2), 1585 (C═N), 1645 (C═C),
oxazol-2-yl)sulfamoyl)acetamide (11a).
Yield 70%; mp:
1687 (C═O), 3377 (NH) cmÀ1 1H NMR (400 MHz,
;
156–158°C; IR (KBr): 1130, 1342 (SO2), 1580 (C═N),
DMSO-d6): δ 3.69 (s, 3H, O–CH3), 4.31 (s, 2H, CH2),
7.06 (s, 1H, C5′–H), 7.37 (s, 1H, C3′–H), 7.40 (s, 1H,
C5–H), 10.38 (bs, 1H, SO2NH), 12.88 (bs, 1H,
imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ
51.8 (O–CH3), 61.0 (CH2), 121.3 (C-5), 123.1 (C-5′),
125.1 (C-3′), 128.6 (C-4′), 139.4 (C-4), 143.2 (C-2′),
154.5 (C-2), 163.7 (C═O) ppm; HRMS (m/z): 358.7672
[M+Na]; Anal. Calcd. for C10H10ClN3O4S2: C, 35.77; H,
3.00; N, 12.51; Found: C, 35.84; H, 3.04; N, 12.44%.
1
1628 (C═C), 1673 (C═O), 3358 (NH) cmÀ1; H NMR
(400 MHz, DMSO-d6): δ 4.20 (s, 2H, CH2), 7.12 (s, 1H,
C5′–H), 7.30–7.54 (m, 5H, C3′–H & Ar–H), 7.69 (s, 1H,
C5–H), 10.42 (bs, 1H, SO2NH), 10.49 (bs, 1H, CONH)
ppm; 13C NMR (100 MHz, DMSO-d6): δ 60.7 (CH2),
149.0 (C-2), 156.9 (C-2″), 169.8 (C═O), 108.1, 113.2,
118.6, 121.8, 122.9, 124.4, 127.1, 128.5, 141.1, 141.9,
144.6, 145.3 (C-4, C-5, C-2′, C-3′, C-4′, C-5′ & aromatic
carbons) ppm; HRMS (m/z): 461.8462 [M+Na]; Anal.
Calcd. for C16H11ClN4O5S2: C, 43.79; H, 2.53; N, 12.77;
Found: C, 43.83; H, 2.48; N, 12.70%.
Methyl
2-(N-(4-(4-nitrothiophen-2-yl)-1H-imidazol-2-yl)
sulfamoyl)acetate (7b). Yield 75%; mp: 178–180°C; IR
(KBr): 1136, 1322 (SO2), 1588 (C═N), 1633 (C═C),
1675 (C═O), 3380 (NH) cmÀ1 1H NMR (400 MHz,
;
N-(Benzo[d]oxazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)
oxazol-2-yl)sulfamoyl)acetamide (11b).
Yield 68%; mp:
DMSO-d6): δ 3.73 (s, 3H, O–CH3), 4.38 (s, 2H, CH2),
7.42 (s, 1H, C5–H), 8.38 (s, 1H, C5′–H), 8.65 (s,
1H, C3′–H), 10.40 (bs, 1H, SO2NH), 12.90 (bs, 1H,
imidazole NH) ppm; 13C NMR (100 MHz, DMSO-d6): δ
52.3 (O–CH3), 62.1 (CH2), 122.9 (C-5), 124.8 (C-3′),
133.4 (C-5′), 139.0 (C-4), 146.8 (C-2′), 152.9 (C-4′),
154.1 (C-2), 165.4 (C═O) ppm; HRMS (m/z): 369.3224
[M+Na]; Anal. Calcd. for C10H10N4O6S2: C, 34.68; H,
2.91; N, 16.18; Found: C, 34.62; H, 2.62; N, 16.15%.
173–175°C; IR (KBr): 1146, 1334 (SO2), 1582 (C═N),
1
1644 (C═C), 1679 (C═O), 3363 (NH) cmÀ1; H NMR
(400 MHz, DMSO-d6): δ 4.17 (s, 2H, CH2), 7.32–7.66
(m, 5H, C5–H & Ar–H), 8.41 (s, 1H, C5′–H), 8.68 (s, 1H,
C3′–H), 10.43 (bs, 1H, SO2NH), 10.51 (bs, 1H, CONH)
ppm; 13C NMR (100 MHz, DMSO-d6): δ 61.6 (CH2),
149.2 (C-4′), 151.7 (C-2), 154.2 (C-2″), 168.1 (C═O),
109.1, 114.5, 117.4, 120.6, 122.3, 126.5, 127.9, 142.1,
142.4, 146.2, 146.8 (C-4, C-5, C-2′, C-3′, C-5′
&
Preparation of dispersed sodium. Clean sodium metal
(10 g) was weighed under dry ether and introduced into a
500 cm3 round-bottomed flask containing sodium-dried
xylene (100 cm3) fitted with an air condenser carrying
calcium chloride guard tube and placed on a sand bath.
The flask was enveloped with a dry cloth, and the sand
bath was heated cautiously. The ring of condensed vapor
of xylene was carefully observed. When the ring of
condensed vapor had risen to the neck of the flask, the
flame was extinguished. The condenser was replaced by
the stopper, and the flask was wrapped with a pre-dried
aromatic carbons) ppm; HRMS (m/z): 472.4023 [M+Na];
Anal. Calcd. for C16H11N5O7S2: C, 42.76; H, 2.47; N,
15.58; Found: C, 42.70; H, 2.43; N, 15.66%.
N-(Benzo[d]thiazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-yl)
oxazol-2-yl)sulfamoyl)acetamide (12a).
Yield 69%; mp:
164–166°C; IR (KBr): 1142, 1345 (SO2), 1586 (C═N),
1
1634 (C═C), 1674 (C═O), 3369 (NH) cmÀ1; H NMR
(400 MHz, DMSO-d6): δ 4.24 (s, 2H, CH2), 7.08 (s, 1H,
C5′–H), 7.45 (s, 1H, C3′–H), 7.59–8.06 (m, 5H, C5–H &
Ar–H), 10.39 (bs, 1H, SO2NH), 12.41 (bs, 1H, CONH)
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2019
Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides
ppm; 13C NMR (100 MHz, DMSO-d6): δ 62.2 (CH2), 166.5
(C═O), 172.4 (C-2″), 115.7, 118.7, 119.3, 121.5, 122.6,
123.0, 124.0, 124.9, 127.4, 139.5, 140.5, 148.1, 152.3 (C-
2, C-4, C-5, C-2′, C-3′, C-4′, C-5′ & aromatic carbons)
ppm; HRMS (m/z): 477.9083 [M+Na]; Anal. Calcd. for
C16H11ClN4O4S3: C, 42.24; H, 2.44; N, 12.32; Found: C,
(400 MHz, DMSO-d6): δ 4.25 (s, 2H, CH2), 7.08 (s, 1H,
C5–H), 7.14 (s, 1H, C5′–H), 7.34–7.62 (m, 5H, C3′ –H,
Ar–H), 10.52 (bs, 1H, CONH), 10.54 (bs, 1H, SO2NH)
ppm; 13C NMR (100 MHz, DMSO-d6): δ 63.5 (CH2),
106.7 (C-5), 164.2 (C-2), 167.4 (C═O), 111.1, 113.4,
118.6, 121.6, 122.8, 123.8, 124.9, 140.2, 141.3, 142.0,
146.5, 150.1 (C-2″) (C-4, C-2′, C-3′, C-4′, C-5′ &
aromatic carbons) ppm; HRMS (m/z): 477.9084 [M+Na];
Anal. Calcd. for C16H11ClN4O4S3: C, 42.24; H, 2.44; N,
42.19; H, 2.49; N, 12.41%.
N-(Benzo[d]thiazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)
oxazol-2-yl)sulfamoyl)acetamide (12b).
Yield 74%; mp:
185–187°C; IR (KBr): 1125, 1323 (SO2), 1581 (C═N),
12.32; Found: C, 42.29; H, 2.48; N, 12.25%.
N-(Benzo[d]oxazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)
1
1647 (C═C), 1677 (C═O), 3376 (NH) cmÀ1; H NMR
(400 MHz, DMSO-d6): δ 4.28 (s, 2H, CH2), 7.62–8.09
(m, 5H, C5–H & Ar–H), 8.36 (s, 1H, C5′–H), 8.70 (s, 1H,
C3′–H), 10.40 (bs, 1H, SO2NH), 12.44 (bs, 1H, CONH)
ppm; 13C NMR (100 MHz, DMSO-d6): δ 63.9 (CH2),
167.3 (C═O), 173.7 (C-2″), 116.4, 117.2, 119.2, 123.6,
124.3, 125.6, 129.1, 130.4, 140.5, 142.1, 147.3, 149.2,
153.8 (C-2, C-4, C-5, C-2′, C-3′, C-4′, C-5′ & aromatic
carbons) ppm; HRMS (m/z): 488.4631 [M+Na]; Anal.
Calcd. for C16H11N5O6S3: C, 41.29; H, 2.38; N, 15.05;
thiazol-2-yl)sulfamoyl)acetamide (14b).
Yield 71%; mp:
176–178°C; IR (KBr): 1126, 1332 (SO2), 1585 (C═N),
1639 (C═C), 1678 (C═O), 3374 (NH) cmÀ1; H NMR
1
(400 MHz, DMSO-d6): δ 4.28 (s, 2H, CH2), 7.10 (s, 1H,
C5–H), 7.37–7.68 (m, 4H, Ar–H), 8.42 (s, 1H, C5′–H),
8.76 (s, 1H, C3′–H), 10.55 (bs, 1H, CONH), 10.56
(bs, 1H, SO2NH)ppm; 13C NMR (100 MHz, DMSO-d6):
δ 64.2 (CH2), 105.1 (C-5), 153.5 (C-2″), 165.7 (C-2),
168.0 (C═O), 109.7, 114.3, 118.6, 122.2, 123.5, 129.9,
141.6, 142.4, 142.6, 147.8, 148.8 (C-4, C-2′, C-3′, C-4′,
C-5′ & aromatic carbons) ppm; HRMS (m/z): 488.4624
[M+Na]; Anal. Calcd. for C16H11N5O6S3: C, 41.29; H,
Found: C, 41.23; H, 2.42; N, 15.15%.
N-(1H-Benz[d]imidazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-
yl)oxazol-2-yl)sulfamoyl)acetamide (13a). Yield 73%; mp:
170–172°C; IR (KBr): 1137, 1331 (SO2), 1594 (C═N),
2.38; N, 15.05; Found: C, 41.26; H, 2.35; N, 15.17%.
N-(Benzo[d]thiazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-yl)
1
1638 (C═C), 1689 (C═O), 3357 (NH) cmÀ1; H NMR
(400 MHz, DMSO-d6): δ 4.23 (s, 2H, CH2), 6.85–7.03
(m, 4H, Ar–H), 7.13 (s, 1H, C5′–H), 7.36 (s, 1H, C3′–H),
7.62 (s, 1H, C5–H), 10.22 (bs, 1H, CONH), 10.42 (bs,
1H, SO2NH), 12.34 (bs, 1H, benzimidazole NH) ppm;
13C NMR (100 MHz, DMSO-d6): δ 61.4 (CH2), 138.6
(C-5), 140.2 (C-2′), 143.7 (C-2″), 146.3 (C-2), 165.6
(C═O), 113.0, 118.2, 120.1, 121.6, 122.2, 123.2, 133.9
(C-4, C-3′, C-4′, C-5′ & aromatic carbons) ppm; HRMS
thiazol-2-yl)sulfamoyl)acetamide (15a).
Yield 66%; mp:
156–158°C; IR (KBr): 1131, 1336 (SO2), 1595 (C═N),
1640 (C═C), 1674 (C═O), 3360 (NH) cmÀ1; H NMR
1
(400 MHz, DMSO-d6): δ 4.22 (s, 2H, CH2), 7.04 (s, 1H,
C5–H), 7.11 (s, 1H, C5′–H), 7.39 (s, 1H, C3′–H), 7.58–
8.03 (m, 4H, Ar–H), 10.46 (bs, 1H, SO2NH), 12.43
(bs, 1H, CONH) ppm; 13C NMR (100 MHz, DMSO-d6):
δ 64.3 (CH2), 103.6 (C-5), 162.1 (C-2), 165.8 (C═O),
172.6 (C-2″), 116.1, 116.8, 119.4, 121.3, 122.4, 122.5,
123.0, 128.2, 138.3, 140.4, 151.7 (C-4, C-2′, C-3′, C-4′,
C-5′ & aromatic carbons) ppm; HRMS (m/z): 493.9682
[M+Na]; Anal. Calcd. for C16H11ClN4O3S4: C, 40.80; H,
2.35; N, 11.90; Found: C, 40.73; H, 2.42; N, 11.96%.
N-(Benzo[d]thiazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)
(m/z):
460.8621
[M+Na];
Anal.
Calcd.
for
C16H12ClN5O4S2: C, 43.89; H, 2.76; N, 15.99; Found:
C, 43.96; H, 2.71; N, 16.05%.
N-(1H-Benz[d]imidazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)
oxazol-2-yl)sulfamoyl)acetamide (13b).
Yield 70%; mp:
194–196°C; IR (KBr): 1128, 1343 (SO2), 1589 (C═N),
1
1629 (C═C), 1681 (C═O), 3381 (NH) cmÀ1; H NMR
thiazol-2-yl)sulfamoyl)acetamide (15b).
Yield 69%; mp:
183–185°C; IR (KBr): 1144, 1324 (SO2), 1582 (C═N),
(400 MHz, DMSO-d6): δ 4.20 (s, 2H, CH2), 6.88–7.06
(m, 4H, Ar–H), 7.64 (s, 1H, C5–H), 8.34 (s, 1H, C5′–H),
8.67 (s, 1H, C3′–H), 10.24 (bs, 1H, CONH), 10.44 (bs,
1H, SO2NH), 12.36 (bs, 1H, benzimidazole NH) ppm;
13C NMR (100 MHz, DMSO-d6): δ 62.5 (CH2),
139.7 (C-5), 141.7 (C-2′), 144.2 (C-2″), 146.1 (C-4′),
148.4 (C-2), 166.8 (C═O), 114.4, 116.9, 122.5, 123.8,
129.3, 135.3 (C-4, C-3′, C-5′ & aromatic carbons) ppm;
HRMS (m/z): 471.4172 [M+Na]; Anal. Calcd. for
C16H12N6O6S2: C, 42.86; H, 2.70; N, 18.74; Found: C,
1635 (C═C), 1685 (C═O), 3379 (NH) cmÀ1; H NMR
1
(400 MHz, DMSO-d6): δ 4.26 (s, 2H, CH2), 7.06 (s, 1H,
C5–H), 7.60–8.07 (m, 4H, Ar–H), 8.37 (s, 1H, C5′–H),
8.71 (s, 1H, C3′–H), 10.47 (bs, 1H, SO2NH), 12.46
(bs, 1H, CONH) ppm; 13C NMR (100 MHz, DMSO-d6):
δ 65.9 (CH2), 104.5 (C-5), 163.7 (C-2), 164.7 (C═O),
173.3 (C-2″), 116.2, 117.2, 120.5, 123.1, 124.6, 127.2,
129.3, 140.4, 141.9, 146.5,152.4 (C-4, C-2′, C-3′, C-4′,
C-5′ & aromatic carbons) ppm; HRMS (m/z): 504.5231
[M+Na]; Anal. Calcd. for C16H11N5O5S4: C, 39.91; H,
42.80; H, 2.64; N, 18.88%.
N-(Benzo[d]oxazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-yl)
2.30; N, 14.54; Found: C, 39.95; H, 2.33; N, 14.62%.
N-(1H-Benz[d]imidazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-
yl)thiazol-2-yl)sulfamoyl)acetamide (16a). Yield 70%; mp:
thiazol-2-yl)sulfamoyl)acetamide (14a).
Yield 68%; mp:
145–147°C; IR (KBr): 1134, 1328 (SO2), 1579 (C═N),
1
1649 (C═C), 1682 (C═O), 3367 (NH) cmÀ1; H NMR
161–163°C; IR (KBr): 1138, 1338 (SO2), 1590 (C═N),
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

T. Rajeswari, T. Rekha, G. Dinneswara Reddy, A. Padmaja, and V. Padmavathi
Vol 000
1
1641 (C═C), 1686 (C═O), 3362 (NH) cmÀ1; H NMR
N-(Benzo[d]thiazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-yl)-
1H-imidazol-2-yl)sulfamoyl)-acetamide (18a).
Yield 66%;
(400 MHz, DMSO-d6): δ 4.24 (s, 2H, CH2), 6.86–7.13 (m,
5H, C5–H, Ar–H), 7.21 (s, 1H, C5′–H), 7.43 (s, 1H, C3′–
H), 10.26 (bs, 1H, CONH), 10.52 (bs, 1H, SO2NH), 12.35
(bs, 1H, benzimidazole NH) ppm; 13C NMR (100 MHz,
DMSO-d6): δ 62.2 (CH2), 102.9 (C-5), 142.8 (C-2′), 145.7
(C-4), 147.6 (C-2″), 163.9 (C-2), 166.3 (C═O), 111.4,
117.5, 120.7, 121.7, 123.1, 134.5 (C-3′, C-4′, C-5′ &
aromatic carbons) ppm; HRMS (m/z): 476.9233 [M+Na];
Anal. Calcd. for C16H12ClN5O3S3: C, 42.34; H, 2.66; N,
mp: 188–190°C; IR (KBr): 1139, 1340 (SO2), 1581
(C═N), 1643 (C═C), 1682 (C═O), 3361 (NH) cmÀ1; H
1
NMR (400 MHz, DMSO-d6): δ 4.23 (s, 2H, CH2), 7.10
(s, 1H, C5′–H), 7.40 (s, 1H, C3′–H), 7.45 (s, 1H, C5–H),
7.57–8.02 (m, 4H, Ar–H), 10.49 (bs, 1H, SO2NH), 12.42
(bs, 1H, CONH), 12.91 (bs, 1H, imidazole NH) ppm; 13C
NMR (100 MHz, DMSO-d6): δ 60.4 (CH2), 168.5
(C═O), 171.6 (C-2″), 114.8, 115.3, 116.3, 118.1, 120.0,
121.1, 122.9, 124.2, 127.2, 134.8, 139.6, 148.9, 150.7
(C-2, C-4, C-5, C-2′, C-3′, C-4′, C-5′ & aromatic
carbons) ppm; HRMS (m/z): 476.9244 [M+Na]; Anal.
Calcd. for C16H12ClN5O3S3: C, 42.34; H, 2.66; N, 15.43;
15.43; Found: C, 42.26; H, 2.60; N, 15.54%.
N-(1H-Benz[d]imidazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)
thiazol-2-yl)sulfamoyl)acetamide (16b).
Yield 68%; mp:
185–187°C; IR (KBr): 1132, 1329 (SO2), 1583 (C═N),
1
1630 (C═C), 1675 (C═O), 3359 (NH) cmÀ1; H NMR
Found: C, 42.42; H, 2.62; N, 15.37%.
(400 MHz, DMSO-d6): δ 4.20 (s, 2H, CH2), 6.89–7.16
(m, 5H, C5–H, Ar–H), 8.40 (s, 1H, C5′–H), 8.74
(s, 1H, C3′–H), 10.28 (bs, 1H, CONH), 10.53 (bs, 1H,
SO2NH), 12.38 (bs, 1H, benzimidazole NH) ppm;
13C NMR (100 MHz, DMSO-d6): δ 63.8 (CH2), 103.4
(C-5), 141.0 (C-2′), 142.2 (C-4), 145.4 (C-2″), 147.3
(C-4′), 164.3 (C-2), 169.7 (C═O), 112.6, 119.5, 122.8,
132.6, 135.2 (C-3′, C-5′ & aromatic carbons) ppm;
HRMS (m/z): 487.4792 [M+Na]; Anal. Calcd. for
C16H12N6O5S3: C, 41.37; H, 2.60; N, 18.09; Found: C,
N-(Benzo[d]thiazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)-1H-
imidazol-2-yl)sulfamoyl)acetamide (18b). Yield 68%; mp:
205–207°C; IR (KBr): 1133, 1326 (SO2), 1591 (C═N),
1
1637 (C═C), 1684 (C═O), 3375 (NH) cmÀ1; H NMR
(400 MHz, DMSO-d6): δ 4.28 (s, 2H, CH2), 7.48 (s, 1H,
C5–H), 7.61–8.10 (m, 4H, Ar–H), 8.38 (s, 1H, C5′–H),
8.73 (s, 1H, C3′–H), 10.52 (bs, 1H, SO2NH), 12.45 (bs,
1H, CONH), 12.93 (bs, 1H, imidazole NH) ppm; 13C
NMR (100 MHz, DMSO-d6): δ 61.2 (CH2), 167.1
(C═O), 172.0 (C-2″), 115.5, 115.9, 116.1, 119.7, 121.8,
123.1, 127.3, 128.6, 135.7, 140.8, 146.4, 149.6, 151.4
(C-2, C-4, C-5, C-2′, C-3′, C-4′, C-5′ & aromatic
carbons) ppm; HRMS (m/z): 487.4793 [M+Na]; Anal.
Calcd. for C16H12N6O5S3: C, 41.37; H, 2.60; N, 18.09;
41.32; H, 2.64; N, 18.15%.
N-(Benzo[d]oxazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-yl)-
1H-imidazol-2-yl)sulfamoyl)-acetamide (17a).
Yield 71%;
mp: 166–168°C; IR (KBr): 1127, 1339 (SO2), 1584
(C═N), 1642 (C═C), 1680 (C═O), 3370 (NH) cmÀ1
;
1H NMR (400 MHz, DMSO-d6): δ 4.21 (s, 2H, CH2),
7.13 (s, 1H, C5′–H), 7.29–7.61 (m, 6H, C5–H, C3′–H,
Ar–H), 10.50 (bs, 1H, CONH), 10.54 (bs, 1H, SO2NH),
12.97 (bs, 1H, imidazole NH) ppm; 13C NMR
(100 MHz, DMSO-d6): δ 64.8 (CH2), 149.4 (C-2),
149.9 (C-2″), 165.3 (C═O), 112.4, 114.1, 116.1, 119.7,
120.2, 121.3, 122.1, 125.3, 135.5, 140.7, 141.2, 145.5
(C-4, C-5, C-2′, C-3′, C-4′, C-5′ & aromatic carbons)
ppm; HRMS (m/z): 460.8623 [M+Na]; Anal. Calcd. for
C16H12ClN5O4S2: C, 43.89; H, 2.76; N, 15.99; Found:
Found: C, 41.46; H, 2.57; N, 18.00%.
N-(1H-Benz[d]imidazol-2-yl)-2-(N-(4-(4-chlorothiophen-2-
yl)-1H-imidazol-2-yl)sulfamoyl)-acetamide (19a).
Yield
72%; mp: 194–196°C; IR (KBr): 1140, 1337 (SO2),
1592 (C═N), 1654 (C═C), 1679 (C═O), 3362 (NH)
1
cmÀ1; H NMR (400 MHz, DMSO-d6): δ 4.23 (s, 2H,
CH2), 6.84–7.05 (m, 4H, Ar–H), 7.14 (s, 1H, C5′–H),
7.38 (s, 1H, C3′–H), 7.43 (s, 1H, C5–H), 10.23 (bs,
1H, CONH), 10.47 (bs, 1H, SO2NH), 12.33 (bs, 1H,
benzimidazole NH), 12.92 (bs, 1H, imidazole NH)
ppm; 13C NMR (100 MHz, DMSO-d6): δ 61.7 (CH2),
140.3 (C-2′), 142.8 (C-2″), 147.2 (C-2), 164.6 (C═O),
113.1, 115.3, 118.6, 120.4, 121.0, 122.5, 132.9, 133.1
(C-4) (C-5, C-3′, C-4′, C-5′ & aromatic carbons) ppm;
HRMS (m/z): 459.8783 [M+Na]; Anal. Calcd. for
C16H13ClN6O3S2: C, 43.99; H, 3.00; N, 19.24; Found:
C, 43.90; H, 3.06; N, 19.33%.
C, 43.84; H, 2.80; N, 16.07%.
N-(Benzo[d]oxazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)-1H-
imidazol-2-yl)sulfamoyl)acetamide (17b). Yield 70%; mp:
173–175°C; IR (KBr): 1141, 1333 (SO2), 1593 (C═N),
1
1631 (C═C), 1676 (C═O), 3382 (NH) cmÀ1; H NMR
(400 MHz, DMSO-d6): δ 4.27 (s, 2H, CH2), 7.33–7.65 (m,
5H, C5–H, Ar–H), 8.41 (s, 1H, C5′–H), 8.75 (s, 1H, C3′–
H), 10.51 (bs, 1H, SO2NH), 10.53 (bs, 1H, CONH), 12.95
(bs, 1H, imidazole NH) ppm; 13C NMR (100 MHz,
DMSO-d6): δ 65.9 (CH2), 150.1 (C-2), 150.7 (C-2″), 167.0
(C═O), 108.7, 113.3, 117.4, 118.3, 121.4, 122.6, 128.7,
136.2, 141.2, 142.5, 146.9, 147.6 (C-4, C-5, C-2′, C-3′, C-
4′, C-5′ & aromatic carbons) ppm; HRMS (m/z): 471.4183
[M+Na]; Anal. Calcd. for C16H12N6O6S2: C, 42.86; H,
2.70; N, 18.74; Found: C, 42.80; H, 2.65; N, 18.66%.
N-(1H-Benz[d]imidazol-2-yl)-2-(N-(4-(4-nitrothiophen-2-yl)-
1H-imidazol-2-yl)sulfamoyl)-acetamide (19b).
Yield 69%;
mp: 210–212°C; IR (KBr): 1145, 1325 (SO2), 1596
(C═N), 1636 (C═C), 1683 (C═O), 3378 (NH) cmÀ1
;
1H NMR (400 MHz, DMSO-d6): δ 4.26 (s, 2H, CH2),
6.87–7.09 (m, 4H, Ar–H), 7.46 (s, 1H, C5–H), 8.36 (s,
1H, C5′–H), 8.72 (s, 1H, C3′–H), 10.25 (bs, 1H,
CONH), 10.48 (bs, 1H, SO2NH), 12.37 (bs, 1H,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2019
Synthesis and Antibacterial Activity of Benzazolyl Azolyl Sulfamoyl Acetamides
[16] Bellina, F.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63,
4571.
benzimidazole NH), 12.94 (bs, 1H, imidazole NH) ppm;
13C NMR (100 MHz, DMSO-d6): δ 62.3 (CH2), 141.4
(C-2′), 143.0 (C-2″), 145.9 (C-4′), 148.5 (C-2), 166.2
(C═O), 114.6, 116.6, 117.1, 122.5, 129.8, 133.8, 134.3
(C-4, C-5, C-3′, C-5′ & aromatic carbons) ppm; HRMS
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[21] Quiroga, J. P.; Insuasty, B. H.; Abonia, R.; Cobo, J.; Sanchez,
(m/z):
470.4331
[M+Na];
Anal.
Calcd.
for
C16H13N7O5S2: C, 42.95; H, 2.93; N, 21.91; Found: C,
42.88; H, 2.90; N, 21.98%.
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Acknowledgments. The authors are grateful to CSIR for financial
assistance under major research project. One of the author
(T. Rekha) is grateful to University Grants Commission (UGC),
New Delhi, for the sanction of UGC-BSR fellowship.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet