Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl Benzoate Analogues

Article abstract of DOI:10.1002/jhet.3209

A convenient one pot synthesis of 20 (1-(2-(benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl benzoate analogues (5a–5t) with ester functionality was carried out via Cu(I) catalyzed click reaction between prop-2-yn-1-yl benzoates and benzyl 2-azidoacetates. The structure of synthesized triazoles were explicated by various spectral techniques like FT-IR, ¹H NMR, ¹³C NMR, and high-resolution mass spectrometry and evaluated for in vitro antimicrobial potential against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae, Enterobacter aerogenes, Candida albicans, and Aspergillus niger. Most of synthesized triazole derivatives exhibited average to excellent activity against tested microbial strains.

Full text of DOI:10.1002/jhet.3209

Month 2018 Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-
1H-1,2,3-triazol-4-yl)methyl Benzoate Analogues
a
Ashima Pahwa,a Devinder Kumar,a Ashwani Kumar,b Dharmendra Singh,c Krishan Kumar,a and
*
C. P. Kaushik,
Raj Luxmia
aDepartment of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, India
bDepartment of Pharmaceutical Sciences, Guru Jambheshwar University of Science and Technology, Hisar, Haryana, India
cCentre for Research and Development, IPCA Lab Ltd., Mumbai, Maharashtra, India
*
E-mail: kaushikcp@gmail.com
Received December 21, 2017
DOI 10.1002/jhet.3209
Published online 00 Month 2018 in Wiley Online Library (wileyonlinelibrary.com).
A convenient one pot synthesis of 20 (1-(2-(benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl benzo-
ate analogues (5a–5t) with ester functionality was carried out via Cu(I) catalyzed click reaction between
prop-2-yn-1-yl benzoates and benzyl 2-azidoacetates. The structure of synthesized triazoles were explicated
by various spectral techniques like FT-IR, 1H NMR, 13C NMR, and high-resolution mass spectrometry and
evaluated for in vitro antimicrobial potential against Staphylococcus aureus, Escherichia coli, Klebsiella
pneumoniae, Enterobacter aerogenes, Candida albicans, and Aspergillus niger. Most of synthesized triazole
derivatives exhibited average to excellent activity against tested microbial strains.
J. Heterocyclic Chem., 00, 00 (2018).
INTRODUCTION
discovered by Sharpless and Meldal [19,20]. This process
has been studied as a unique example of click reaction
and widely used in the synthesis of pharmaceuticals [21],
peptidomematics [22], dendritic and polymeric materials
[23], glycoconjugates [24], and calixsugars [25].
Keeping these observations in mind and in
continuation of our enduring research on synthesis and
biological studies of 1,4-disubstituted 1,2,3-triazoles
[26–29], herein, we focused on synthesis of a series
Over the past few decades, incidence of drug resistant
pathogenic microbial infections is increasing at an
alarming rate; thereby, total reliability on the available
antimicrobial drugs is not advisable in the long run for
medicinal chemists. This aroused a crucial search for
development of new antimicrobials with better efficacy.
In order to meet this challenge, 1,2,3-triazoles emerged as
a privileged class of medicinal scaffolds [1,2] due to its
better compatibility. Among N-heterocycles, disubstituted
1,2,3-triazoles have been preferably used as an important
pharmacophore owing to the widespread therapeutic
importance as antibiofilm [3], antibiotic [4], antimicrobial
[5,6], anticancer [7,8], antitubercular [9,10], antiinfluenza
[11], antiproliferative [12], antioxidant [13], and
antimalarial [14]. In addition to the aforementioned
medicinal importance, 1,2,3-triazoles also possess
paramount impact in the fields like drug discovery [15],
bioconjugation [16], and material sciences [17].
of
(1-(2-(benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)
methyl benzoate analogues (5a–5t) with ester
functionality via Cu(I) catalyzed click reaction between
prop-2-yn-1-yl benzoates and benzyl 2-azidoacetates.
All the synthesized compounds were characterized by
spectral techniques FT-IR, 1H NMR, 13C NMR
spectroscopy, and high-resolution mass spectrometry
(HRMS) and also examined for antimicrobial activity.
RESULTS AND DISCUSSION
Cu(I) catalyzed version of thermally driven Huisgen 1,3-
dipolar cycloaddition [18] between terminal alkynes and
azides emerged as a powerful tool for the exclusive
Chemistry. The synthesis of desired (1-(2-(benzyloxy)-
2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl
benzoate
construction
of
1,4-disubstituted
1,2,3-triazoles
analogues (5a–5t) having ester linkage was accomplished
© 2018 Wiley Periodicals, Inc.

C. P. Kaushik, A. Pahwa, D. Kumar, A. Kumar, D. Singh, K. Kumar, and R. Luxmi
Vol 000
by strategy described in Scheme 1. Commercially
available benzoyl chlorides (1a–1d) were taken as
starting material for the synthesis of prop-2-yn-1-yl
benzoates [30] (2a–2d) by propargylation with propargyl
alcohol in dry dichloromethane in the presence of N,N-
dimethylaminopyridine. Benzyl 2-bromoacetates (4a–4e)
were prepared by treating various benzyl alcohols (3a–
3e) with bromoacetyl bromide in acetonitrile using
sodium bicarbonate as base. Finally, the synthesis of 1,4-
disubstituted 1,2,3-triazoles with ester linkage (5a–5t) in
good yield was carried out via one pot click reaction
between prop-2-yn-1-yl benzoates (2a–2d) and benzyl 2-
azidoacetates (4a–4e) (generated in situ by reaction of
benzyl 2-bromoacetates (4a–4e) with sodium azide) in
the presence of catalytic amount of copper sulfate
pentahydrate and sodium ascorbate in dimethyl sulfoxide
(DMSO).
resolution mass spectral analysis were found in good
agreement with their molecular mass.
Antimicrobial evaluation.
All the newly synthesized
1,4-disubstituted 1,2,3-triazole derivatives (5a–5t) having
ester linkage were tested in vitro for antimicrobial activity
against one Gram-positive bacterial strain [Staphylococcus
aureus (MTCC 3160)], three Gram-negative bacterial
strains [Escherichia coli (MTCC 443), Klebsiella
pneumoniae (NCDC 138), and Enterobacter aerogenes
(NCDC 106)] and two fungi [Candida albicans (MTCC
227) and Aspergillus niger (MTCC 282)] by serial dilution
technique [31]. Norfloxacin and fluconazole were used as
standard drugs for antibacterial and antifungal strains,
respectively, and minimum inhibitory concentrations
(MICs) were expressed in terms of μmol/mL.
Antibacterial screening data (Table 1) depicted that some
of the tested compounds possess good to excellent
bactericidal potential. Compound 5m exhibited
appreciable bactericidal potential against all bacterial
strains under study, while compound 5n showed
remarkable activity against S. aureus and E. coli with
MIC value of 0.0290 μmol/mL. Compound 5h with MIC
0.0293 μmol/mL found to possess significant inhibitory
activity against K. pneumoniae. Compound 5k (MIC
0.0315), 5o (MIC 0.0305), and 5r (MIC 0.0305) against
S. aureus; 5g (MIC 0.0304) and 5s (MIC 0.0313) against
E. coli; and 5i (MIC 0.0301) and 5r (MIC 0.0305)
against K. pneumoniae showed comparable activity with
standard drug. In case of E. aerogenes, compound 5c
(MIC 0.0631), 5h (MIC 0.0586), 5n (MIC 0.0580), and
5r (MIC 0.0609) found to be moderately active as
compared with reference.
Compound
R1
R2
Time (h)
Yield (%)
5a
5b
5c
5d
5e
5f
5g
5h
5i
H
H
H
H
H
OCH3
OCH3
OCH3
OCH3
OCH3
NO2
NO2
NO2
NO2
NO2
CH3
CH3
CH3
CH3
H
9
12
11
8
10
11
13
12
7
14
12
13
14
8
10
12
11
10
7
83
89
72
85
84
79
81
78
83
85
76
88
83
73
77
89
81
83
80
77
OCH3
NO2
Cl
CH3
H
OCH3
NO2
Cl
CH3
H
OCH3
NO2
Cl
CH3
H
OCH3
NO2
Cl
5j
5k
5l
5m
5n
5o
5p
5q
5r
5s
5t
As revealed from the results represented in Table 2,
some of the triazole derivatives exhibited moderate to
good antifungal activity against tested strains. Compound
5h displayed almost twofold antifungal potency against
C. albicans with MIC value of 0.0293 μmol/mL.
Compound 5m (MIC 0.0142) also emerged as a potential
antifungal agent against C. albicans, while compound 5h
(MIC 0.0144) possessed comparable efficacy with
standard drug, fluconazole, against A. niger.
CH3
CH3
12
The structures of all newly synthesized triazole
derivatives (5a–5t) were confirmed by spectral
techniques, that is, FT-IR, 1H NMR, 13C NMR
spectroscopy, and HRMS. In FT-IR spectra of
compounds, emergence of characteristic absorption bands
in the region at 3126–3156 cmꢀ1 due to C–H stretching
vibrations of triazole ring ensured formation of triazoles,
while absorption bands at 1698–1764 cmꢀ1 attributed to
Structure and activity relationship studies. From these
antimicrobial activity results, following structure–activity
relationships can be surmised:
• In most of cases, triazole derivatives possessing
4-nitrobenzoate as well as 4-nitrobenzyl moiety
displayed enhanced bactericidal and fungicidal potential
against all the tested strains. Thereby, it can be clearly
depicted that the presence of electron withdrawing nitro
group on benzyl/benzoate moiety enhances antimicrobial
activity. Owing to this, compound 5m with nitro group
on both benzyl/benzoate moiety showed excellent
potency against all tested strains except A. niger.
1
>C¼O stretching vibrations of ester. In H NMR spectra
of most of compounds, proton present on C5 of newly
formed triazole ring resonated in region at δ 7.80–8.38 as
singlet. Moreover, in 13C NMR spectra, signals appeared
in the region at δ 125.4–127.1 and 141.5–143.7 assigned
to C5 and C4 of triazole ring, respectively. Signals due to
carbonyl carbon (>C¼O) of ester linkages appeared in
the region at δ 163.9–167.6. Results obtained from high-
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-
1,2,3-triazol-4-yl)methyl Benzoate Analogues
Scheme 1. Synthesis of ester-linked 1,4-disubstituted 1,2,3-triazoles (5a–5t).
Table 1
In vitro antibacterial evaluation of 1,4-disubstituted 1,2,3-triazoles (5a–5t).
Minimum inhibitory concentration (μmol/mL)
Gram-negative bacteria
Gram-positive bacteria
Compound
Staphylococcus aureus
Escherichia coli
Klebsiellae pneumoniae
Enterobacter aerogenes
5a
5b
5c
5d
5e
5f
5g
5h
5i
5j
5k
5l
5m
5n
5o
5p
0.2846
0.1311
0.0631
0.1296
0.2737
0.1311
0.0608
0.0586
0.0601
0.0632
0.0315
0.0586
0.0142
0.0290
0.0305
0.1368
0.0632
0.0305
0.0625
0.1318
0.0391
0.2846
0.1311
0.1262
0.2592
0.2737
0.1311
0.0304
0.0586
0.0601
0.0632
0.0631
0.0586
0.0283
0.0290
0.0609
0.1368
0.0632
0.0609
0.0313
0.1318
0.0391
0.2846
0.0656
0.0631
0.1296
0.2737
0.0656
0.0608
0.0293
0.0301
0.1265
0.0631
0.0586
0.0283
0.0580
0.1218
0.1368
0.0632
0.0305
0.0625
0.0659
0.0391
0.2846
0.1311
0.0631
0.2592
0.2737
0.1311
0.1215
0.0586
0.1202
0.1265
0.1262
0.1173
0.0283
0.0580
0.1218
0.1368
0.1265
0.0609
0.1251
0.1318
0.0783
5q
5r
5s
5t
Norfloxacin
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

C. P. Kaushik, A. Pahwa, D. Kumar, A. Kumar, D. Singh, K. Kumar, and R. Luxmi
Vol 000
Table 2
EXPERIMENTAL
In vitro antifungal evaluation of 1,4-disubstituted 1,2,3-triazoles (5a–5t).
Chemistry. The reagents used were obtained from Alfa
Aesar, HiMedia, and Sigma-Aldrich, used without further
purification. Melting points of the synthesized
compounds were determined on electrothermal melting
point apparatus in open capillary tubes and are
uncorrected. To monitor the progress of reaction, thin-
layer chromatography was performed on precoated silica
gel plates (SIL G/UV254, ALUGRAM) in ethyl acetate–
hexane mixture and visualized under ultraviolet light. FT-
IR spectra were scanned on SHIMAZDU IR AFFINITY-I
Minimum inhibitory concentration (μmol/mL)
Compound
Candida albicans
Aspergillus niger
5a
5b
5c
5d
5e
5f
5g
5h
5i
5j
5k
5l
5m
5n
5o
5p
0.1423
0.1311
0.1262
0.1296
0.1368
0.0656
0.0608
0.0293
0.0601
0.0632
0.0631
0.0586
0.0142
0.0580
0.0609
0.1368
0.0632
0.0609
0.0625
0.0659
0.0408
0.1423
0.0656
0.0631
0.0648
0.1368
0.0656
0.0608
0.0144
0.0301
0.0316
0.0315
0.0586
0.1218
0.0580
0.1218
0.0342
0.0632
0.0305
0.0313
0.0659
0.0102
FT-IR in KBr and wave numbers (ν) reported in cmꢀ1
.
1H NMR spectra and 13C NMR spectra were scanned on
BRUKER AVANCE II 400 MHz spectrometer (Bruker
Corporation, Billerica, MA) at 400 and 100 MHz,
respectively, in CDCl3 or DMSO-d6. Chemical shift
values (δ) were quoted in parts per million (ppm).
Coupling constant values (J) were reported in hertz (Hz).
HRMS were performed on Waters Micromass Q-Tof
Micro (ESI) spectrometer (Waters Corporation, Milford,
MA), and values are reported in m/z.
5q
5r
5s
5t
Fluconazole
General procedure for synthesis of (1-(2-(benzyloxy)-2-
oxoethyl)-1H-1,2,3-triazol-4-yl)methyl benzoate analogues
(5a–5t). To synthesize prop-2-yn-1-yl benzoates (2a–2d)
[30], commercially available benzoyl chlorides (1.0 mmol)
(1a–1d) were added dropwise into the stirred and cooled
(0–10°C) solution of propargyl alcohol (1.0 mmol) in dry
• The presence of electron donating methyl and methoxy
groups on benzoate moiety displayed improved antimi-
crobial activity as compared with unsubstituted benzoate
moiety.
dichloromethane
using
N,N-dimethylaminopyridine
• In comparison between methyl and methoxy groups,
majority of triazole derivatives with 4-methoxy benzyl
substitutent behave as better antimicrobial agent than
derivatives with 4-methyl benzyl substitutent.
• Generally, triazole derivatives having 4-chlorobenzyl
moiety exhibited significant improvement in antimicro-
bial activity than compounds possessing unsubstituted
benzyl moiety.
(1.2 mmol) as base, further allowed stirring to continue for
2–4 h. Upon completion of reaction, neutralized reaction
contents with dilute HCl and extracted with
dichloromethane (3 × 30 mL). Organic layer was distilled
under vacuum to get desired alkynes (2a–2d).
Synthesis of benzyl 2-bromoacetates (4a–4e) were carried
out by dissolving bromoacetyl bromide (1.2 mmol) dropwise
into the stirred solution of benzyl alcohols (3a–3e)
(1.0 mmol) in acetonitrile in the presence of sodium
bicarbonate (1.5 mmol) as base at 0–4°C, continued stirring
for further 45 min. As the reaction was completed, the
product was extracted with dichloromethane (3 × 30 mL).
Organic layer was evaporated under reduced pressure.
In the final step, to carry out the synthesis of triazole
derivatives (5a–5t), benzyl 2-bromoacetates (1.0 mmol)
(4a–4e) and aqueous sodium azide (3.0 mmol) were
reacted in DMSO for 1 h at 25–40°C with continuous
stirring. Thereafter, prop-2-yn-1-yl benzoates (2a–2d)
were added to the aforementioned reaction mixture
followed by aqueous copper sulfate pentahydrate
(0.1 mmol) and sodium ascorbate (0.4 mmol) at the same
temperature with continuous stirring for 7–14 h. Reaction
progress was monitored by thin-layer chromatography.
As the reaction was completed, ice-cold water was added
to the reaction mixture. Solid precipitates thus obtained
CONCLUSION
Conclusively, synthesis of a series (1-(2-(benzyloxy)-
2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl
benzoate
analogues (5a–5t) having ester functionality was
accomplished through convenient approach of Cu(I)
catalyzed click reaction and evaluated for in vitro
antimicrobial screening. Most of the synthesized triazole
derivatives displayed moderate to excellent activity
against bacterial strains. Among the tested triazoles,
compound 5m exhibited more potency than standard drug
against all bacterial strains and C. albicans, while
compound 5n found to possess noteworthy activity
against S. aureus, E. coli, E. aerogenes, among all
bacterial strains.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-
1,2,3-triazol-4-yl)methyl Benzoate Analogues
were filtered and washed with ammonia solution and
recrystallized by chloroform/hexane (8:2) to furnish pure
products (5a–5t) in good yield.
HRMS (m/z) calculated for C19H16N4O6 [M + H]+:
397.1103. Found: 397.1068.
(1-(2-((4-Chlorobenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl benzoate (5d). Appearance: white solid; Yield:
Characterization of synthesized compounds (5a–5t).
(1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl
benzoate (5a). Appearance: white solid; Yield: 83%, mp:
85%; mp: 108–112°C; FT-IR (KBr): νmax = 3137 (C–H
str., triazole ring), 3081 (C–H str., aromatic ring), 2952
(C–H str., aliphatic), 1759, 1698 (C¼O str., ester), 1600,
1449 (C¼C str., aromatic ring), 1276 (C–O asym. str.,
96–100°C; FT-IR (KBr): νmax = 3152 (C–H str., triazole
ring), 3031 (C–H str., aromatic ring), 2975 (C–H str.,
aliphatic), 1764, 1708 (C¼O str., ester), 1597, 1452
(C¼C str., aromatic ring), 1259 (C–O asym. str., ester),
ester) 1054 (C–O sym. str., ester) cmꢀ1 1H NMR
;
(400 MHz, CDCl3): δ = 5.19 (s, 2H, NCH2), 5.22 (s, 2H,
OCH2), 5.50 (s, 2H, OCH2), 7.25–7.28 (m, 2H, Ar–H),
7.33 (d, 2H, Ar–H, J = 8.4 Hz), 7.42–7.46 (m, 2H, Ar–
H), 7.57 (t, 1H, Ar–H, J = 7.2 Hz), 7.86 (s, 1H, C–H
triazole), 8.04 (d, 2H, Ar–H, J = 7.2 Hz) ppm; 13C NMR
(100 MHz, CDCl3): δ = 50.8, 58.0, 67.2, 125.4 (C5
triazole), 128.4, 129.0, 129.7, 129.9, 132.9, 133.3, 134.8,
143.5 (C4 triazole), 166.0 (C¼O ester), 166.4 (C¼O
ester) ppm; HRMS (m/z) calculated for C19H16ClN3O4
[M + H]+: 386.0908 (35Cl), 388.0878 (37Cl). Found:
1
1049 (C–O sym. str., ester) cmꢀ1; H NMR (400 MHz,
CDCl3): δ = 5.22 (s, 2H, NCH2), 5.23 (s, 2H, OCH2),
5.52 (s, 2H, OCH2), 7.33–7.59 (m, 8H, Ar–H), 7.86 (s,
1H, C–H triazole), 8.05 (d, 2H, Ar–H, J = 8.4 Hz)
ppm; 13C NMR (100 MHz, CDCl3): δ = 50.9, 58.0,
68.1, 125.4 (C5 triazole), 128.4, 128.6, 128.8, 128.9,
129.7, 129.8, 133.2, 134.5, 143.4 (C4 triazole), 166.1
(C¼O ester), 166.4 (C¼O ester) ppm; HRMS (m/z)
calculated for C19H17N3O4 [M + H]+: 352.1253. Found:
386.0838 (35Cl), 388.0801 (37Cl).
352.1226.
(1-(2-((4-Methylbenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl benzoate (5e). Appearance: white solid; Yield:
(1-(2-((4-Methoxybenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl benzoate (5b). Appearance: white solid; Yield:
84%; mp: 136–140°C; FT-IR (KBr): νmax = 3141 (C–H
str., triazole ring), 3070 (C–H str., aromatic ring), 2969
(C–H str., aliphatic), 1761, 1710 (C¼O str., ester), 1597,
1451 (C¼C str., aromatic ring), 1271 (C–O asym. str.,
89%; mp: 96–100°C; FT-IR (KBr): νmax = 3144 (C–H
str., triazole ring), 3081 (C–H str., aromatic ring), 2958
(C–H str., aliphatic), 1750, 1702 (C¼O str., ester), 1613,
1450 (C¼C str., aromatic ring), 1277 (C–O asym. str.,
ester), 1047 (C–O sym. str., ester) cmꢀ1 1H NMR
;
ester), 1054 (C–O sym. str., ester) cmꢀ1 1H NMR
;
(400 MHz, CDCl3): δ = 2.41 (s, 3H, CH3), 5.20 (s, 2H,
NCH2), 5.23 (s, 2H, OCH2), 5.44 (s, 2H, OCH2), 7.07–
7.14 (m, 4H, Ar–H), 7.38–7.42 (m, 2H, Ar–H), 7.54 (t,
1H, Ar–H, J = 7.2 Hz), 8.00 (d, 2H, Ar–H, J = 7.2 Hz),
8.08 (s, 1H, C–H triazole) ppm; 13C NMR (100 MHz,
CDCl3): δ = 21.7, 50.8, 57.7, 68.0, 125.4 (C5 triazole),
128.4, 128.7, 129.4, 129.7, 129.9, 131.5, 133.4, 138.8,
143.4 (C4 triazole), 166.1 (C¼O ester), 166.3 (C¼O
ester) ppm; HRMS (m/z) calculated for C20H19N3O4
(400 MHz, CDCl3): δ = 3.66 (s, 3H, OCH3), 5.08 (s, 2H,
NCH2), 5.11 (s, 2H, OCH2), 5.38 (s, 2H, OCH2), 6.77 (d,
2H, Ar–H, J = 8.4 Hz), 7.17 (d, 2H, Ar–H, J = 8.4 Hz),
7.31–7.35 (m, 2H, Ar–H), 7.46 (t, 1H, Ar–H,
J = 7.2 Hz), 7.80 (s, 1H, C–H triazole), 7.93 (d, 2H, Ar–
H, J = 7.2 Hz) ppm; 13C NMR (100 MHz, CDCl3):
δ = 50.8, 55.2, 57.9, 67.8, 114.0, 125.5 (C5 triazole),
126.6, 128.3, 129.6, 129.8, 130.4, 133.2, 143.1 (C4
triazole), 159.9, 166.2 (C¼O ester), 166.4 (C¼O ester)
ppm; HRMS (m/z) calculated for C20H19N3O5 [M + H]+:
[M + H]+: 366.1409. Found: 366.1378.
(1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl
4-methoxybenzoate (5f). Appearance: white solid; Yield:
382.1358. Found: 382.1329.
(1-(2-((4-Nitrobenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)
methyl benzoate (5c).
Appearance: white solid; Yield:
79%; mp: 76–80°C; FT-IR (KBr): νmax = 3154 (C–H str.,
triazole ring), 3081 (C–H str., aromatic ring), 2935 (C–H
str., aliphatic), 1761, 1710 (C¼O str., ester), 1607, 1457
(C¼C str., aromatic ring), 1278 (C–O asym. str., ester),
72%; mp: 102–106°C; FT-IR (KBr): νmax = 3148 (C–H
str., triazole ring), 3059 (C–H str., aromatic ring), 2952
(C–H str., aliphatic), 1760, 1718 (C¼O str., ester), 1603,
1451 (C¼C str., aromatic ring), 1524 (N–O asym. str.,
NO2), 1315 (N–O sym. str., NO2), 1270 (C–O asym. str.,
1
1054 (C–O sym. str., ester) cmꢀ1; H NMR (400 MHz,
DMSO-d6): δ = 3.83 (s, 3H, OCH3), 5.22 (s, 2H, NCH2),
5.40 (s, 2H, OCH2), 5.51 (s, 2H, OCH2), 7.05 (d, 2H,
Ar–H, J = 8.8 Hz), 7.35–7.39 (m, 5H, Ar–H), 7.92 (d,
2H, Ar–H, J = 8.8 Hz), 8.28 (s, 1H, C–H triazole) ppm;
13C NMR (100 MHz, DMSO-d6): δ = 50.9, 56.0, 58.0,
67.3, 114.6, 122.0, 126.8 (C5 triazole), 128.6, 128.8,
128.9, 131.8, 135.8, 143.3 (C4 triazole), 163.8, 165.6
(C¼O ester), 167.6 (C¼O ester) ppm; HRMS (m/z)
calculated for C20H19N3O5[M + H]+: 382.1358. Found:
382.1327.
ester), 1068 (C–O sym. str., ester) cmꢀ1 1H NMR
;
(400 MHz, CDCl3): δ = 5.29 (s, 2H, NCH2), 5.31 (s, 2H,
OCH2), 5.50 (s, 2H, OCH2), 7.41–7.48 (m, 4H, Ar–H),
7.57 (t, 1H, Ar–H, J = 7.6 Hz), 7.89 (s, 1H, C–H
triazole), 8.03 (d, 2H, Ar–H, J = 7.6 Hz), 8.18 (d, 2H,
Ar–H, J = 8.8 Hz) ppm; 13C NMR (100 MHz, CDCl3):
δ = 50.8, 57.9, 66.4, 123.9, 125.5 (C5 triazole), 128.4,
128.7, 129.6, 129.7, 133.3, 141.5 (C4 triazole), 143.6,
148.0, 165.8 (C¼O ester), 166.4 (C¼O ester) ppm;
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

C. P. Kaushik, A. Pahwa, D. Kumar, A. Kumar, D. Singh, K. Kumar, and R. Luxmi
Vol 000
(1-(2-((4-Methoxybenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-methoxybenzoate (5g).
(1-(2-((4-Methylbenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-methoxybenzoate (5j). Appearance: white solid;
Appearance: white
solid; Yield: 81%; mp: 72–76°C; FT-IR (KBr):
νmax = 3148 (C–H str., triazole ring), 3076 (C–H str.,
aromatic ring), 2947 (C–H str., aliphatic), 1756, 1701
(C¼O str., ester), 1606, 1457 (C¼C str., aromatic ring),
1271 (C–O asym. str., ester), 1057 (C–O sym. str., ester)
Yield: 85%; mp: 80–84°C; FT-IR (KBr): νmax = 3148 (C–H
str., triazole ring), 3087 (C–H str., aromatic ring), 2963 (C–
H str., aliphatic), 1762, 1706 (C¼O str., ester), 1607, 1463
(C¼C str., aromatic ring), 1277 (C–O asym. str., ester),
1
1057 (C–O sym. str., ester) cmꢀ1; H NMR (400 MHz,
cmꢀ1
;
1H NMR (400 MHz, CDCl3): δ = 3.81 (s, 3H,
DMSO-d6): δ = 2.41 (s, 3H, CH3), 3.83 (s, 3H, OCH3),
5.16 (s, 2H, NCH2), 5.21 (s, 2H, OCH2), 5.48 (s, 2H,
OCH2), 7.05 (d, 2H, Ar–H, J = 8.8 Hz),7.07–7.14 (m,
4H, Ar–H), 7.92 (d, 2H, Ar–H, J = 8.8 Hz), 8.28 (s, 1H,
C–H triazole) ppm; 13C NMR (100 MHz, DMSO-d6):
δ = 21.1, 50.9, 55.3, 58.0, 68.0, 114.1, 122.0, 126.0 (C5
triazole), 128.6, 129.3, 131.5, 131.8, 138.8, 142.6 (C4
triazole), 163.6, 165.6 (C¼O ester), 167.6 (C¼O ester)
ppm; HRMS (m/z) calculated for C21H21N3O5 [M + H]+:
396.1515. Found: 396.1485.
OCH3), 3.85 (s, 3H, OCH3), 5.16 (s, 2H, NCH2), 5.18 (s,
2H, OCH2), 5.46 (s, 2H, OCH2), 6.88–6.92 (m, 4H, Ar–
H), 7.28 (d, 2H, Ar–H, J = 8.4 Hz), 7.84 (s, 1H, C–H
triazole), 7.99 (d, 2H, Ar–H, J = 8.8 Hz) ppm; 13C NMR
(100 MHz, CDCl3): δ = 50.9, 55.3, 55.4, 57.7, 68.0,
113.7, 114.1, 122.1, 125.4 (C5 triazole), 126.6, 130.5,
131.8, 143.6 (C4 triazole), 160.1, 163.6, 166.1 (C¼O
ester), 166.2 (C¼O ester) ppm; HRMS (m/z) calculated
for C21H21N3O6 [M + H]+: 412.1464. Found: 412.1431.
(1-(2-((4-Nitrobenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)
methyl 4-methoxybenzoate (5h). Appearance: white solid;
(1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl
4-nitrobenzoate (5k).
Appearance: white solid; Yield:
Yield: 78%; mp: 136–140°C; FT-IR (KBr): νmax = 3126
(C–H str., triazole ring), 3081 (C–H str., aromatic ring),
2969 (C–H str., aliphatic), 1718, 1703 (C¼O str., ester),
1608, 1447 (C¼C str., aromatic ring), 1512 (N–O asym.
str., NO2), 1317 (N–O sym. str., NO2), 1275 (C–O
76%; mp: 80–84°C; FT-IR (KBr): νmax = 3143 (C–H str.,
triazole ring), 3081 (C–H str., aromatic ring), 2963 (C–H
str., aliphatic), 1747, 1718 (C¼O str., ester), 1610, 1463
(C¼C str., aromatic ring), 1545 (N–O asym. str., NO2),
1353 (N–O sym. str., NO2), 1266 (C–O asym. str., ester),
1
asym. str., ester), 1049 (C–O sym. str., ester) cmꢀ1; H
1
1049 (C–O sym. str., ester) cmꢀ1; H NMR (400 MHz,
NMR (400 MHz, DMSO-d6): δ = 3.83 (s, 3H, OCH3),
5.21 (s, 2H, NCH2), 5.40 (s, 2H, OCH2), 5.51 (s, 2H,
OCH2), 7.03 (d, 2H, Ar–H, J = 9.2 Hz), 7.46 (d, 2H,
Ar–H, J = 8.4 Hz), 7.92 (d, 2H, Ar–H, J = 9.2 Hz),
8.18 (d, 2H, Ar–H, J = 8.4 Hz), 8.38 (s, 1H, C–H
triazole) ppm; 13C NMR (100 MHz, DMSO-d6):
δ = 50.9, 56.0, 57.8, 66.4, 114.6, 121.9, 123.9, 126.0
(C5 triazole), 128.7, 131.9, 141.5, 143.3 (C4 triazole),
148.0, 163.8, 164.5 (C¼O ester), 167.5 (C¼O ester)
ppm; HRMS (m/z) calculated for C20H18N4O7[M + H]+:
CDCl3): δ = 5.01 (s, 2H, NCH2), 5.09 (s, 2H, OCH2),
5.30 (s, 2H, OCH2), 7.13–7.26 (m, 5H, Ar–H), 7.80 (s,
1H, C–H triazole), 7.97–8.05 (m, 4H, Ar–H) ppm; 13C
NMR (100 MHz, CDCl3): δ = 50.4, 58.3, 67.4, 123.1,
125.6 (C5 triazole), 128.0, 128.2, 128.3, 130.4, 134.2,
134.7, 141.8 (C4 triazole), 150.1, 163.9 (C¼O ester),
165.9 (C¼O ester) ppm; HRMS (m/z) calculated for
C19H16N4O6 [M + H]+: 397.1103. Found: 397.1071.
(1-(2-((4-Methoxybenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-nitrobenzoate (5l).
Appearance: white solid;
Yield: 88%; mp: 86–90°C; FT-IR (KBr): νmax = 3154 (C–
H str., triazole ring), 3070 (C–H str., aromatic ring), 2957
(C–H str., aliphatic), 1747, 1719 (C¼O str., ester), 1611,
1466 (C¼C str., aromatic ring), 1543 (N–O asym. str.,
NO2), 1352 (N–O sym. str., NO2), 1267 (C–O asym. str.,
427.1209. Found: 427.1188.
(1-(2-((4-Chlorobenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-methoxybenzoate (5i). Appearance: white solid;
Yield: 83%; mp: 102–106°C; FT-IR (KBr): νmax = 3137
(C–H str., triazole ring), 3087 (C–H str., aromatic ring),
2980 (C–H str., aliphatic), 1751, 1712 (C¼O str., ester),
1607, 1421 (C¼C str., aromatic ring), 1261 (C–O asym.
ester), 1055 (C–O sym. str., ester) cmꢀ1 1H NMR
;
(400 MHz, CDCl3): δ = 3.80 (s, 3H, OCH3), 5.17 (s, 2H,
NCH2), 5.21 (s, 2H, OCH2), 5.53 (s, 2H, OCH2), 6.88 (d,
2H, Ar–H, J = 8.4 Hz), 7.28 (d, 2H, Ar–H, J = 8.4 Hz),
7.89 (s, 1H, C-H triazole), 8.11–8.26 (m, 4H, Ar–H)
ppm; 13C NMR (100 MHz, CDCl3): δ = 50.9, 55.3, 58.7,
68.1, 114.1, 123.5, 125.7 (C5 triazole), 126.5, 130.5,
130.9, 135.1, 142.5 (C4 triazole), 150.6, 160.1, 164.5
(C¼O ester), 166.1 (C¼O ester) ppm; HRMS (m/z)
calculated for C20H18N4O7 [M + H]+: 427.1209. Found:
427.1171.
str., ester), 1052 (C–O sym. str., ester) cmꢀ1; H NMR
1
(400 MHz, DMSO-d6): δ = 3.84 (s, 3H, OCH3), 5.21 (s,
2H, NCH2), 5.40 (s, 2H, OCH2), 5.51 (s, 2H, OCH2),
7.05 (d, 2H, Ar–H, J = 9.2 Hz), 7.41–7.45 (m, 4H, Ar–
H), 7.92 (d, 2H, Ar–H, J = 9.2 Hz), 8.27 (s, 1H, C–H
triazole) ppm; 13C NMR (100 MHz, DMSO-d6):
δ = 50.9, 56.0, 58.0, 66.4, 114.6, 122.0, 126.8 (C5
triazole), 128.9, 130.3, 131.8, 133.3, 134.8, 142.6 (C4
triazole), 163.8, 165.6 (C¼O ester), 167.6 (C¼O ester)
ppm; HRMS (m/z) calculated for C20H18ClN3O5
[M + H]+: 416.1013 (35Cl), 418.0984 (37Cl). Found:
416.0928 (35Cl), 418.0903 (37Cl).
(1-(2-((4-Nitrobenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)
methyl 4-nitrobenzoate (5m).
Appearance: white solid;
Yield: 83%; mp: 144–148°C; FT-IR (KBr): νmax = 3154
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-
1,2,3-triazol-4-yl)methyl Benzoate Analogues
(C–H str., triazole ring), 3081 (C–H str., aromatic ring),
2996 (C–H str., aliphatic), 1764, 1728 (C¼O str., ester),
1609, 1449 (C¼C str., aromatic ring), 1522 (N–O asym.
str., NO2), 1346 (N–O sym. str., NO2), 1274 (C–O asym.
1456 (C¼C str., aromatic ring), 1264 (C–O asym. str.,
ester), 1053 (C–O sym. str., ester) cmꢀ1 1H NMR
;
(400 MHz, CDCl3): δ = 2.41 (s, 3H, CH3), 5.21 (s, 2H,
NCH2), 5.23 (s, 2H, OCH2), 5.48 (s, 2H, OCH2), 7.23 (d,
2H, Ar–H, J = 8.0 Hz), 7.33–7.38 (m, 5H, Ar–H), 7.85
(s, 1H, C–H triazole), 7.94 (d, 2H, Ar–H, J = 8.0 Hz)
ppm; 13C NMR (100 MHz, CDCl3): δ = 21.7, 50.9, 57.9,
68.1, 125.4 (C5 triazole), 126.9, 128.6, 128.8, 128.9,
129.1, 129.8, 134.5, 143.6 (C4 triazole), 144.0, 166.0
(C¼O ester), 166.5 (C¼O ester) ppm; HRMS (m/z)
calculated for C20H19N3O4 [M + H]+: 366.1409. Found:
1
str., ester), 1053 (C–O sym. str., ester) cmꢀ1; H NMR
(400 MHz, DMSO-d6): δ = 5.37 (s, 2H, NCH2), 5.51 (s,
2H, OCH2), 5.59 (s, 2H, OCH2), 7.65 (d, 2H, Ar–H,
J = 8.4 Hz), 8.17–8.23 (m, 4H, Ar–H), 8.34 (d, 2H, Ar–
H, J = 8.8 Hz), 8.35 (s, 1H, C–H triazole) ppm; 13C
NMR (100 MHz, DMSO-d6): δ = 50.8, 58.6, 66.3, 123.5,
123.9, 125.5 (C5 triazole), 128.7, 130.4, 135.2, 141.5,
142.5 (C4 triazole), 147.9, 150.6, 164.4 (C¼O ester),
166.4 (C¼O ester) ppm; HRMS (m/z) calculated for
366.1379.
(1-(2-((4-Methoxybenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-methylbenzoate (5q). Appearance: White solid;
C19H15N5O8 [M + H]+: 442.0954. Found: 442.0919.
(1-(2-((4-Chlorobenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-nitrobenzoate (5n). Appearance: white solid;
Yield: 81%; mp: 116–120°C; FT-IR (KBr): νmax = 3148
(C–H str., triazole ring), 3081 (C–H str., aromatic ring),
2963 (C–H str., aliphatic), 1752, 1712 (C¼O str., ester),
1609, 1446 (C¼C str., aromatic ring), 1278 (C–O asym.
Yield: 73%; mp: 116–120°C; FT-IR (KBr): νmax = 3154
(C–H str., triazole ring), 3081 (C–H str., aromatic ring),
2975 (C–H str., aliphatic), 1750, 1718 (C¼O str., ester),
1610, 1491 (C¼C str., aromatic ring), 1545 (N–O asym.
str., NO2), 1353 (N–O sym. str., NO2), 1266 (C–O asym.
1
str., ester), 1055 (C–O sym. str., ester) cmꢀ1; H NMR
(400 MHz, CDCl3): δ = 2.41 (s, 3H, CH3), 3.81(s, 3H,
OCH3), 5.17 (s, 2H, NCH2), 5.18 (s, 2H, OCH2),
5.48 (s, 2H, OCH2), 6.89 (d, 2H, Ar–H, J = 8.4 Hz),
7.21–7.29 (m, 4H, Ar–H), 7.84 (s, 1H, C–H triazole),
7.93 (d, 2H, Ar–H, J = 8.0 Hz) ppm; 13C NMR
(100 MHz, CDCl3): δ = 21.7, 50.9, 55.3, 57.9, 68.0,
114,1, 125.4 (C5 triazole), 126.6, 127.0, 129.1, 129.8,
130.5, 143.5 (C4 triazole), 144.0, 160.1, 166.1
(C¼O ester), 166.5 (C¼O ester) ppm; HRMS (m/z)
calculated for C21H21N3O5 [M + H]+: 396.1515. Found:
1
str., ester), 1049 (C–O sym. str., ester) cmꢀ1; H NMR
(400 MHz, DMSO-d6): δ = 5.21 (s, 2H, NCH2), 5.50 (s,
2H, OCH2), 5.53 (s, 2H, OCH2), 7.39–7.45 (m, 4H, Ar–
H), 8.17–8.20 (m, 2H, Ar–H), 8.33–8.37 (m, 3H, Ar–
H
+
C–H triazole) ppm; 13C NMR (100 MHz,
DMSO-d6): δ = 50.9, 59.1, 66.4, 124.4, 127.1 (C5
triazole), 128.9, 130.4, 131.2, 133.4, 134.9, 135.2, 142.0
(C4 triazole), 150.7, 164.5 (C¼O ester), 167.5 (C¼O
ester) ppm; HRMS (m/z) calculated for C19H15ClN4O6
[M + H]+: 431.0758 (35Cl), 433.0729 (37Cl). Found:
396.1490.
(1-(2-((4-Nitrobenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)
431.0674 (35Cl), 433.0650 (37Cl).
methyl 4-methylbenzoate (5r).
Appearance: white solid;
Yield: 83%; mp: 96–100°C; FT-IR (KBr): νmax = 3156
(C–H str., triazole ring), 3081 (C–H str., aromatic ring),
2963 (C–H str., aliphatic), 1760, 1719 (C¼O str., ester),
1608, 1446 (C¼C str., aromatic ring), 1517 (N–O asym.
str., NO2), 1353 (N–O sym. str., NO2), 1279 (C–O asym.
(1-(2-((4-Methylbenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-nitrobenzoate (5o). Appearance: white solid;
Yield: 77%; mp: 82–86°C; FT-IR (KBr): νmax = 3143 (C–
H str., triazole ring), 3078 (C–H str., aromatic ring), 2993
(C–H str., aliphatic), 1743, 1726 (C¼O str., ester), 1606,
1457 (C¼C str., aromatic ring), 1533 (N–O asym. str.,
NO2), 1350 (N–O sym. str., NO2), 1291 (C–O asym. str.,
1
str., ester), 1053 (C–O sym. str., ester) cmꢀ1; H NMR
(400 MHz, CDCl3): δ = 2.40 (s, 3H, CH3), 5.29 (s, 2H,
NCH2), 5.30 (s, 2H, OCH2), 5.48 (s, 2H, OCH2), 7.22 (d,
2H, Ar–H, J = 8.0 Hz), 7.46 (d, 2H, Ar–H, J = 8.4 Hz),
7.88–7.92 (m, 3H, Ar–H + C–H triazole), 8.17 (d, 2H,
Ar–H, J = 8.4 Hz) ppm; 13C NMR (100 MHz, CDCl3):
δ = 21.7, 50.8, 57.8, 66.4, 123.9, 125.5 (C5 triazole),
126.8, 128.7, 129.2, 129.7, 141.5, 143.7 (C4 triazole),
144.1, 147.9, 165.8 (C¼O ester), 166.5 (C¼O ester)
ppm; HRMS (m/z) calculated for C20H18N4O6 [M + H]+:
ester), 1053 (C–O sym. str., ester) cmꢀ1 1H NMR
;
(400 MHz, CDCl3): δ = 2.25 (s, 3H, CH3), 5.09 (s, 2H,
NCH2), 5.15 (s, 2H, OCH2), 5.43 (s, 2H, OCH2), 7.06–
7.14 (m, 4H, Ar–H), 7.85 (s, 1H, C–H triazole), 8.09–
8.17 (m, 4H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3):
δ = 21.1, 50.8, 58.6, 67.9, 123.5, 125.7 (C5 triazole),
128.6, 129.3, 130.8, 131.4, 135.1, 138.7, 142.3 (C4
triazole), 150.5, 164.4 (C¼O ester), 166.1 (C¼O ester)
ppm; HRMS (m/z) calculated for C20H18N4O6 [M + H]+:
411.1260. Found: 411.1222.
411.1260. Found: 411.1225.
(1-(2-((4-Chlorobenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-methylbenzoate (5s). Appearance: white solid;
(1-(2-(Benzyloxy)-2-oxoethyl)-1H-1,2,3-triazol-4-yl)methyl
4-methylbenzoate (5p).
Appearance: white solid; Yield:
Yield: 80%; mp: 90–94°C; FT-IR (KBr): νmax = 3143
(C–H str., triazole ring), 3048 (C–H str., aromatic ring),
2935 (C–H str., aliphatic), 1746, 1717 (C¼O str., ester),
1612, 1452 (C¼C str., aromatic ring), 1291 (C–O asym.
89%; mp: 104–108°C; FT-IR (KBr): νmax = 3150 (C–H
str., triazole ring), 3070 (C–H str., aromatic ring), 2975
(C–H str., aliphatic), 1760, 1706 (C¼O str., ester), 1610,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

C. P. Kaushik, A. Pahwa, D. Kumar, A. Kumar, D. Singh, K. Kumar, and R. Luxmi
Vol 000
1
str., ester), 1053 (C–O sym. str., ester) cmꢀ1; H NMR
(400 MHz, CDCl3): δ = 2.41 (s, 3H, CH3), 5.18 (s, 2H,
NCH2), 5.21 (s, 2H, OCH2), 5.48 (s, 2H, OCH2), 7.22–
7.33 (m, 6H, Ar–H), 7.85 (s, 1H, C–H triazole), 7.93 (d,
2H, Ar–H, J = 8.4 Hz) ppm; 13C NMR (100 MHz,
CDCl3): δ = 21.7, 50.8, 57.8, 67.2, 125.4 (C5 triazole),
126.9, 129.0, 129.1, 129.8, 129.9, 132.9, 134.8, 143.6
(C4 triazole), 144.0, 166.0 (C¼O ester), 166.5 (C¼O
standard drugs, respectively, which were also assessed
under similar experimental conditions for comparison
with the tested compounds. After incubation, microbial
growth was checked visually, and results were recorded
in terms of MIC (μmol/mL).
Acknowledgment. Authors are highly thankful to University
Grants Commission, New Delhi for financial assistance.
ester) ppm; C20H18ClN3O4 [M
+
H]+: 400.1064
(35Cl), 402.1035 (37Cl). Found: 400.0991 (35Cl),
402.0957 (37Cl).
(1-(2-((4-Methylbenzyl)oxy)-2-oxoethyl)-1H-1,2,3-triazol-4-
yl)methyl 4-methylbenzoate (5t). Appearance: white solid;
REFERENCES AND NOTES
[1] Kaushik, C. P.; Kumar, K.; Lal, K.; Narasimhan, B.; Kumar, A.
Monatsh Chem 2016, 147, 817.
[2] Kaushik, C. P.; Pahwa, A.; Thakur, R.; Kaur, P. Synth
Commun 2017, 47, 368.
[3] Nagender, P.; Reddy, G. M.; Kumar, R. N.; Poornachandra, Y.;
Kumar, C. G.; Narsaiah, B. Bioorg Med Chem Lett 2014, 24, 2905.
[4] Aufort, M.; Herscovici, J.; Bouhours, P.; Moreau, N.; Girard,
C. Bioorg Med Chem Lett 2008, 18, 1195.
[5] Kaushik, C. P.; Kumar, K.; Singh, D.; Singh, S. K.; Jindal, D.
K.; Luxmi, R. Synth Commun 2015, 45, 1977.
Yield: 77%; mp: 104–108°C; FT-IR (KBr): νmax = 3143
(C–H str., triazole ring), 3053 (C–H str., aromatic ring),
2986 (C–H str., aliphatic), 1760, 1709 (C¼O str., ester),
1610, 1452 (C¼C str., aromatic ring), 1266 (C–O asym.
1
str., ester), 1052 (C–O sym. str., ester) cmꢀ1; H NMR
(400 MHz, CDCl3): δ = 2.36 (s, 3H, CH3), 2.41 (s, 3H,
CH3), 5.19 (s, 2H, NCH2), 5.20 (s, 2H, OCH2), 5.49 (s,
2H, OCH2), 7.17–7.25 (m, 6H, Ar–H), 7.85 (s, 1H, C–H
triazole), 7.94 (d, 2H, Ar–H, J = 8.4 Hz) ppm; 13C
NMR (100 MHz, CDCl3): δ = 21.2, 21.7, 50.9, 57.9,
68.1, 125.4 (C5 triazole), 127.0, 128.7, 129.1, 129.4,
129.8, 131.5, 138.8, 143.6 (C4 triazole), 144.0, 166.1
(C¼O ester), 166.5 (C¼O ester) ppm; HRMS (m/z)
calculated for C21H21N3O4 [M + H]+: 380.1566. Found:
380.1538.
[6] Kaushik, C. P.; Kumar, K.; Lal, K.; Singh, S. K. Chem Biol In-
teract 2014, 4, 341.
[7] Sukerkar, P. A.; MacRenaris, K. W.; Townsend, T. R.; Ahmed,
R. A.; Burdette, J. E.; Meade, T. J. Bioconjug Chem 2011, 22, 2304.
[8] Kuntala, N.; Telu, J. R.; Banothu, V.; Nallapati, S. B.;
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General procedure for in vitro antimicrobial evaluation.
In vitro antimicrobial evaluation of newly synthesized
ester-linked triazoles (5a–5t) was carried out against
four bacterial strains, namely, S. aureus (MTCC 3160),
E. coli (MTCC 443), K. pneumoniae (NCDC 138),
E. aerogenes (NCDC 106), and two fungi, namely,
C. albicans (MTCC 227) and A. niger (MTCC 282),
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of test compounds in DMSO with concentration
200 μg/mL were prepared (2.0 mg of the test compound
in 10 mL DMSO). Fresh cultures of respective
microorganisms were prepared by inoculating in suitable
media, that is, nutrient broth for bacterial strains and
potato dextrose broth for fungal strains, respectively,
then incubated at 37
1°C for 24 h (all bacteria),
25 1°C for 7 days (A. niger), and 37 1°C for 48 h
(C. albicans). Stock solutions of test compounds were
serially diluted in test tubes containing 1 mL of sterile
medium to obtain the concentrations of 100 to 6.25 μg/
mL. After that, 100 μL of the broth containing the test
microorganism in sterile saline was inoculated in each
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37
1°C for 48 h (C. albicans), and 25
1°C for
7 days (A. niger). For antibacterial and antifungal
screening, norfloxacin and fluconazole were taken as
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet

Month 2018
Synthesis and Antimicrobial Evaluation of (1-(2-(Benzyloxy)-2-oxoethyl)-1H-
1,2,3-triazol-4-yl)methyl Benzoate Analogues
[27] Kaushik, C. P.; Pahwa, A.; Kumar, A.; Singh, D.; Kumar, K.
Synth Commun 2017, 47, 1485.
SUPPORTING INFORMATION
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Chem Lett 2012, 22, 4353.
Additional supporting information may be found online
in the Supporting Information section at the end of the
article.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet