Regioselective one-pot synthesis of 1,4-disubstituted 1,2,3-triazole derivatives

Article abstract of DOI:10.1515/hc-2014-0179

The one-pot synthesis of novel 1,4-disubstituted 1,2,3-triazole derivatives derived from homopropargyl alcohol backbones has been accomplished. Triazoles are obtained in good yields from a variety of readily available aromatic and aliphatic halides withou

Full text of DOI:10.1515/hc-2014-0179

Heterocycl. Commun. 2014; 20(6): 361–364
Ayşegül Gümüş* and Sibel Uçur
Regioselective one-pot synthesis of
,4-disubstituted 1,2,3-triazole derivatives
1
Abstract: The one-pot synthesis of novel 1,4-disubstituted The advantages of the second method are in situ genera-
,2,3-triazole derivatives derived from homopropargyl tion of Cu(I) salts needed for the catalysis from the stable
1
alcohol backbones has been accomplished. Triazoles are Cu(II) sulfate-sodium ascorbate redox system, in addition
obtained in good yields from a variety of readily available to the in situ generation of a potentially toxic and explo-
aromatic and aliphatic halides without isolation of poten- sive organic azide without isolation. Only the 1,4-disubsti-
tially unstable organic azide intermediates.
tuted isomer can be isolated.
Homopropargyl alcohols are good candidates for the
Keywords: homopropargyl alcohols; one-pot synthesis; preparation of substituted triazoles. We report herein effi-
organic azide; 1,2,3-triazoles.
cient, safe, and regioselective one-pot synthesis of novel
1
,4-disubstituted 1,2,3-triazole derivatives having poten-
tial to possess various biological activities.
DOI 10.1515/hc-2014-0179
Received October 24, 2014; accepted November 2, 2014
Results and discussion
Introduction
Triazole-containing compounds show various biological
activities including antimicrobial [1, 2], anti-inflammatory
The parent homopropargylic alcohols 2a and 2b, used as
templates in this work for the construction of 1,4-disub-
stituted 1,2,3-triazoles, were synthesized by the addition
reaction of propargyl bromide to aldehydes in the pres-
ence of the Zn-Cu couple (Scheme 1).
[
[
3], antidepressant [4, 5], anticonvulsant [6, 7], antifungal
8, 9], enzyme inhibition [10, 11] activities. 1,2,3-Triazoles
Terminal acetylenes on homopropargylic alcohol
derivatives 2a,b make them valuable candidates for
one-pot synthesis of the target triazole structures. Ali-
phatic and aromatic azides can easily be generated from
the corresponding halides as intermediates used in
one-pot method [22–26]. The operational simplicity of this
method makes it attractive for wide variety of applications.
Initially, 1-phenylbut-3-yn-1-ol 2a was employed in one-
pot, two-step procedure for trapping generated organic
azides to afford the corresponding triazole products.
Various aromatic and allylic halides were screened under
the reported optimized conditions [25] and newl triazole
products 3–10 were obtained in good yields (Scheme 2).
have also a wide range applications in industry as anticor-
rosive agents, dyes, photostabilizers, photographic mate-
rials, and agrochemicals [12–14]. Remarkable stability
toward metabolic transformations, H-bonding capability,
and high dipole moment make triazoles attractive build-
ing components [15–17].
In organic chemistry, one-pot multicomponent reac-
tions have received much attention because they minimize
the time and cost of the synthesis of highly functional
molecules from simple building blocks [18–20]. Moreover,
one-pot multicomponent reactions result in better yields,
thus minimizing extra operations like isolation, handling,
and chromatography.
1
-(2-Thienyl)but-3-yn-1-ol 2b was also allowed to react
The Huisgen 1,3-dipolar cycloadditions of azides
and alkynes are regioselective, yielding 1,4-disubstituted
with aryl and allyl halides and sodium azide according to
the same procedure. New triazole derivatives 11–18 were
isolated in good yields (Scheme 2).
1
,2,3-triazoles [21]. The regioselective one-pot synthesis of
,4-disubstituted 1,2,3-triazoles has been reported [22–26].
1
*
Corresponding author: Ayşegül Gümüş, Department of Chemistry,
Conclusion
New 1,4-disubstituted 1,2,3-triazole derivatives of poten-
tial biological activity were synthesized directly from
Yuzuncu Yil University, Van 65080, Turkey,
e-mail: gumusa@gmail.com
Sibel Uçur: Department of Chemistry, Yuzuncu Yil University, Van
6
5080, Turkey
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62ꢀꢁꢁꢁꢂꢀA. Gümüş and S. Uçur: Synthesis of 1,4-disubstituted 1,2,3-triazole derivatives
O
OH
The mixture was heated at reflux for 4 h with monitoring by TLC and
then hydrolyzed with 1 ꢀ HCl (5 mL) and extracted with diethyl ether
Propargyl bromide
Zn/Cu, dry THF
R
H
R
(3 ꢀ× ꢀ3 0 mL). The extract was dried over MgSO and concentrated on a
4
1
a,b
2a,b
rotary evaporator. The crude product (residue) was purified by flash
column chromatography using a mixture of ethyl acetate and hex-
anes.
a: R = Ph
b: R = 2-thienyl
Scheme 1ꢀ
1
1
-Phenylbut-3-yn-1-ol (2a):ꢁYellow oil; yield 4.33 g (80%); H NMR:
δ 7.65–6.31 (m, 5H), 4.78 (m, 1H), 3.06 (bs,1H), 2.62–2.40 (m, 2H), 2.08–
.16 (m, 1H); C NMR: δ 142.5, 128.5, 128.0, 127.8, 126.1, 125.8, 80.8,
1
3
1
CuSO4 5H O
Sodium ascorbate
2
OH
R1
OH
N
N
72.3, 71.0, 29.4.
2
NaN3 R -X
N
R2
R1
L-proline, Na CO3
2
1
DMSO:H O
1-(2-Thienyl)but-3-yn-1-ol (2b):ꢁYellow oil; yield 4.12 g (73%); H
NMR: δ 7.10 (dd, J ꢀ= ꢀ 1.2 and 5.0 Hz, 1H), 6.88–6.87 (m, 1H), 6.82 (dd,
J ꢀ= ꢀ 3.5 and 5.0 Hz, 1H), 4.90 (t, J ꢀ= ꢀ 6.2 Hz, 1H), 3.37 (bs,1H), 2.55 (dd,
2
a,b
2
3-18
: R1 = Ph; R2 = Ph
11: R1 = 2-thienyl; R2 = Ph
3
4
5
6
7
8
9
1
: R = Ph; R2 = 4-hydroxyphenyl 12: R1 = 2-thienyl; R2 = 4-hydroxyphenyl
1
1
3
1
2
1
2
J ꢀ= ꢀ 2.6 and 6.1 Hz, 2H), 1.96 (t, J ꢀ= ꢀ 2.6 Hz, 1H); C NMR: δ 146.4, 126.7,
: R = Ph; R = p-tolyl
13: R = 2-thienyl; R = p-tolyl
: R = Ph; R2 = 1-naphtyl
1
14: R1 = 2-thienyl; R2 = 1-naphtyl
125.0, 124.3, 80.5, 71.6, 68.4, 29.4.
1
2
1
2
: R = Ph; R = 3-pyridinyl
: R = Ph; R2 = 3-thiophenyl
15: R = 2-thienyl; R = 3-pyridinyl
1
16: R1 = 2-thienyl; R2 = 3-thiophenyl
: R = Ph; R2 = allyl
1
17: R1 = 2-thienyl; R2 = allyl
0: R1 = Ph; R2 = Bn
18: R1 = 2-thienyl; R2 = Bn
General procedure for the synthesis of 1,4-disubstituted
1
,2,3-triazoles 3-18
Scheme 2ꢀ
A mixture of an aromatic or aliphatic halide (1 mmol), homoprop-
argyl alcohol (1 mmol), ꢂ-proline (24 mg, 0.2 mmol), Na CO3 (24
homopropargylic alcohols by the reaction with various
aryl and allyl halides and sodium azide.
2
mg, 0.2 mmol), NaN (65 mg, 1 mmol), sodium ascorbate (20 mg,
3
0
.1 mmol), DMSO/H O (18:2, 20 mL), and CuSO ·5H O solution (1 ꢀ,
2 4 2
.05 mL) in a 20-mL scintillation vial was stirred overnight at 65°C.
0
The crude mixture was poured into cold dilute NH OH solution
4
(
30 mL) and extracted with ethyl acetate (4 ꢀ× ꢀ2 0 mL). The collected
Experimental
General
organic layer was washed with brine, dried over MgSO , and concen-
4
trated in vacuo. The crude product was purified by flash column chro-
matography using mixtures of ethylacetate and hexanes.
1
-Phenyl-2-(1-phenyl-1H-1,2,3-triazol-4-yl)ethanolꢀ(3):ꢁWhite crys-
1H NMR (400 MHz) and 13C NMR (100 MHz) spectra were recorded
1
tals; yield 244 mg, 92%); mp 120–123°C; H NMR: δ 7.66 (s, 1H), 7.59
in CDCl on a Bruker Spectrospin Avance DPX-400 spectrometer. HR
3
(
d, J ꢀ= ꢀ 8.0 Hz, 2H), 7.43–7.39 (m, 2H), 7.35–7.31 (m, 2H), 7.28–7.24 (m,
H), 7.21–7.18 (m, 1H), 5.03 (dd, J ꢀ= ꢀ 4.9 and 7.6 Hz, 1H), 3.44 (bs, 1H),
mass spectra were obtained on an Agilent Technologies 6224 Accu-
rate-Mass TOF LC/MS instrument at the National Nanotechnology
Research Center of Bilkent University (UNAM). Flash column chro-
matography was performed using thick-walled glass columns with a
flash grade (Merck Silica Gel 60). Reactions were monitored by thin
layer chromatography (TLC) using precoated silica gel plates (Merck
Silica Gel PF-254), visualized by UV light and polymolybden phos-
phoric acid in ethanol as appropriate.
3
1
3
3
.12–3.10 (m, 2H); C NMR: δ 144.5, 142.6, 136.0, 128.7, 127.7, 127.4, 126.6,
+
1
24.8, 119.4, 72.1, 34.4. HRMS (ESI-TOF). Calcd for C H N O [M+H] :
1
6
15
3
m/z 266.12879. Found: m/z 266.12903.
4
-(4-(2-Hydroxy-2-phenylethyl)-1H-1,2,3-triazol-1-yl)phenolꢀ(4):ꢁ
1
Yellow crystals; yield 175 mg (62%); mp 115–116°C. H NMR: δ 7.56 (s,
1
H), 7.38–7.27 (m, 9H), 5.35–5.33 (m, 1H), 4.99 (bs, 1H), 3.14–3.12 (m,
1
3
2
H); C NMR: δ 144.9, 143.4, 140.4, 128.5, 127.8, 127.7, 125.8, 125.7, 120.3,
+
1
06.9, 73.1, 35.3. HRMS (ESI-TOF). Calcd for C H N O [M+H] : m/z
1
6
15
3
2
General procedure for the synthesis of homopropargyl
alcohols 2a,b
2
82.12370. Found: m/z 282.12484.
1
-Phenyl-2-(1-p-tolyl-1H-1,2,3-triazol-4-yl)ethanol (5):ꢁWhite crys-
1
tals; yield 136 mg, 49%); mp 130–131°C; H NMR: δ 7.62 (s, 1H), 7.48–
The Zn-Cu couple preparation was conducted under an oxygen-free
environment. Zinc dust (9.54 g, 74 mmol) was suspended in distilled
water (10 mL), and the mixture was treated with acidic cupric chlo-
ride solution (0.15 ꢀ in 5% hydrochloric acid, 22 mL) with vigorous
magnetic stirring. When the evolution of the gas ceased, the suspen-
sion was filtered and the black solid was washed with water until the
7
.18 (m, 9H), 5.03 (dd, J ꢀ= ꢀ 4.7 and 7.7 Hz, 1H), 3.50 (bs, 1H), 3.12–3.09
1
3
(
m, 2H), 2.33 (s, 3H); C NMR: δ 145.3, 143.6, 138.8, 134.8, 130.2, 128.5,
27.7, 125.8, 120.4, 73.2, 35.5, 21.1. HRMS (ESI-TOF). Calcd for C H N O
1
17 17
3
+
[
M+H] : m/z 280.14444. Found: m/z 280.14609.
wash gave a negative test for chloride with 6% silver nitrate solution. 2-(1-(1-Naphthyl)-1H-1,2,3-triazol-4-yl)-1-phenylethanolꢀ(6):ꢁ
1
To a stirred mixture of aldehyde 2a,b (37 mmol) and freshly prepared White crystals; yield 217 mg (69%); mp 118–120°C; H NMR: δ 8.00–
dry Zn-Cu couple (5.16 g, 40 mmol) in THF (30 mL), propargyl bro- 7.93 (m, 2H), 7.60–7.26 (m, 11H), 5.18–5.22 (m, 1H), 3.57 (bs, 1H), 3.28
1
3
mide (6 g, 40 mmol, 80 wt% in toluene) was added dropwise at 0°C. (d, J ꢀ= ꢀ 6.2 Hz, 2H); C NMR: δ 144.6, 143.6, 134.1, 133.7, 130.3, 128.4,
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A. Gümüş and S. Uçur: Synthesis of 1,4-disubstituted 1,2,3-triazole derivativesꢀꢂꢁꢁꢁꢀ363
1
(
3
28.2, 127.8, 127.6, 127.0, 125.9, 125.0, 123.5, 122.3, 73.3, 35.4. HRMS 2-(1-(1-Naphthyl-1H-1,2,3-triazol-4-yl)-1-(2-thienyl)ethanolꢀ(14):ꢁ
+
1
ESI-TOF). Calcd for C H N O [M+H] : m/z 316.14444. Found: m/z White crystals; yield 239 mg (74%) mp 110–112°C; H NMR: δ 8.00–7.92
20 17 3
16.14692.
(m, 2H), 7.68 (s, 1H), 7.58–7.49 (m, 5H), 7.26–7.24 (m, 1H), 7.02–6.96 (m,
1
3
2
H), 5.47–5.43 (m, 1H), 3.85 (bs, 1H), 3.39 (d, J ꢀ= ꢀ 6.0 Hz, 2H); C NMR:
δ 147.6, 144.1, 134.0, 133.6, 130.3, 128.4, 128.2, 127.8, 127.0, 126.7, 125.1,
1
-Phenyl-2-(1-(3-pyridyl)-1H-1,2,3-triazol-4-yl)ethanol (7):ꢁWhite
1
125.0, 124.6, 123.8, 123.5, 122.3, 69.4, 35.6. HRMS (ESI-TOF). Calcd for
crystals; yield 239 mg (90%); mp 132–134°C; H NMR: δ 8.90 (d, J ꢀ= ꢀ
+
C H N OS [M+Na] : m/z 344.08280. Found: m/z 344.08742.
1.9 Hz, 1H), 8.66–8.64 (m, 1H), 8.12–8.10 (m, 1H), 7.81 (s, 1H), 7.50–7.47
18 15
3
(
1
m, 1H), 7.43–7.27 (m, 5H), 5.14–5.11 (m, 1H), 3.24–3.22 (m, 2H), 2.98 (s,
1
3
2-(1-(3-Pyridyl)-1H-1,2,3-triazol-4-yl)-1-(thiophen-2-yl)ethanol (15):ꢁ
H); C NMR: δ 149.5, 146.1, 143.6, 141.2, 133.7, 128.5, 128.1, 127.8, 125.8,
1
+
Yellow crystals; yield 177 mg (65%) mp 123–126°C; H NMR: δ 8.94–
1
24.3, 120.4, 73.0, 35.5. HRMS (ESI-TOF). Calcd for C H N O [M+H] :
15
14
4
8
.93 (m, 1H), 8.67–8.65 (m, 1H), 8.16–8.13 (m, 1H), 7.88 (s, 1H), 7.53–7.49
m/z 267.12404. Found: m/z 267.12701.
(
m, 1H), 7.28–7.25 (m, 1H), 7.02–7.01 (m, 1H), 6.99–6.96 (m, 1H), 5.40–
1
3
5
.37 (m, 1H), 4.91 (bs, 1H), 3.37–3.34 (m, 2H); C NMR: δ 149.4, 147.4,
1
-Phenyl-2-(1-(3-thienyl)-1H-1,2,3-triazol-4-yl)ethanol
(8):ꢁLight
1
45.6, 141.0, 133.7, 128.3, 126.7, 124.7, 124.5, 123.9, 120.6, 69.1, 35.6. HRMS
1
yellow crystals; yield 225 mg; (83%) mp 128–130°C; H NMR: δ 7.59 (s,
+
(
ESI-TOF). Calcd for C H N OS [M+Na] : m/z 295.06240. Found: m/z
13 12 4
1
1
H), 7.43–7.42 (m, 1H), 7.36–7.32 (m, 4H), 7.29–7.26 (m, 2H), 7.23–7.19 (m,
H), 5.03 (dd, J ꢀ= ꢀ 4.8 and 7.8 Hz, 1H), 3.11–3.10 (m, 2H), 3.09 (bs, 1H);
295.06733.
1
3
C NMR: δ 145.1, 143.5, 135.9, 128.5, 127.7, 127.2, 125.8, 120.8, 114.0, 73.2,
1
-(2-Thienyl)-2-(1-(3-thienyl)-1H-1,2,3-triazol-4-yl)ethanolꢀ(16):ꢁ
+
3
5.4. HRMS (ESI-TOF). Calcd for C H N OS [M+Na] : m/z 294.06715.
14
13
3
1
Yellow crystals; yield 186 mg (67%); mp 124–126°C; H NMR: δ 7.72 (s,
Found: m/z 294.07159.
1
H), 7.51 (s, 1H), 7.43 (s, 2H), 7.27–7.24 (m, 1H), 6.99–6.96 (m, 2H), 5.37–
1
3
5
.35 (m, 1H), 3.68 (bs, 1H), 3.30–3.28 (m, 2H); C NMR: δ 144.8, 142.0,
2
-(1-allyl-1H-1,2,3-triazol-4-yl)-1-phenylethanol (9):ꢁYellow crys-
1
32.3, 124.6, 124.1, 122.1, 121.3, 118.3, 118.2, 111.4, 66.8, 32.9. HRMS
1
tals; yield 170 mg (74%); mp 72–74°C; H NMR: δ 7.297.16 (m, 6H), 5.93–
+
(
ESI-TOF). Calcd for C H N OS [M+Na] : m/z 300.02357. Found: m/z
12 11 3 2
5
.84 (m, 1H), 5.23 (dd, J ꢀ= ꢀ 1.0 and 10.2 Hz, 1H), 5.15 (dd, J ꢀ= ꢀ 0.9 and 17.0 300.02736.
Hz, 1H), 4.95 (dd, J ꢀ= ꢀ 5.1 and 7.5 Hz, 1H), 4.82 (d, J ꢀ= ꢀ 6.2 Hz, 2H), 4.25
bs, 1H), 3.03–3.01 (m, 2H); 13C NMR: δ 145.0, 143.6, 131.2, 128.4, 127.5,
25.8, 122.1, 120.0, 73.1, 52.6, 35.4. HRMS (ESI-TOF). Calcd for C H N O
(
1
2
-(1-Allyl-1H-1,2,3-triazol-4-yl)-1-(2-thienyl)ethanol
(17):ꢁYellow
1
1
3
15
3
crystals; yield 168 mg (71%); mp 69–71°C; H NMR: δ 7.33 (s, 1H),
+
[
M+H] : m/z 230.12879. Found: m/z 230.13119.
7.23–7.21 (m, 1H), 6.94–6.93 (m, 2H), 6.02–5.92 (m, 1H), 5.33–5.21 (m,
1
3
3H), 4.92–4.91 (m, 2H), 3.22–3.21 (m, 2H); C NMR: δ 147.7, 144.4, 131.2,
2
-(1-Benzyl-1H-1,2,3-triazol-4-yl)-1-phenylethanolꢀ(10):ꢁWhite 126.5, 124.3, 123.6, 122.3, 119.9, 69.1, 52.5, 35.6. HRMS (ESI-TOF). Calcd
1
for C H N OS [M+Na] : m/z 258.06715. Found: m/z 258.07055.
+
crystals; yield 180 mg (65%); mp 117–120°C; H NMR: δ 7.29–7.10 (m,
11 13
3
1
1H), 5.39 (s, 2H), 4.96 (dd, J ꢀ= ꢀ 4.9 and 7.6 Hz, 1H), 3.02–3.00 (m, 2H);
1
3
C NMR: δ 144.1, 142.5, 133.5, 128.1, 127.7, 127.3, 127.0, 126.5, 124.7, 121.1, 2-(1-Benzyl-1H-1,2,3-triazol-4-yl)-1-(2-thienyl)ethanolꢀ(18):ꢁ
+
1
7
2
2.1, 53.1, 34.4. HRMS (ESI-TOF). Calcd for C H N O [M+H] : m/z Yellow crystals; yield 200 mg (70%); mp 112–114°C; H NMR: δ 7. 3 8 –
17 17 3
80.14444. Found: m/z 280.14765.
7.34 (m, 3H), 7.23–7.20 (m, 4H), 6.93–6.92 (m, 2H), 5.49 (d, J ꢀ= ꢀ 2.6 Hz,
1
3
2
H), 5.29 (dd, J ꢀ= ꢀ 5.1 and 6.9 Hz, 1H), 3.20–3.18 (m, 2H); C NMR: δ
1
47.3, 144.8, 134.6, 129.1, 128.7, 128.0, 126.6, 124.5, 123.6, 122.1, 69.4, 54.1,
2
-(1-Phenyl-1H-1,2,3-triazol-4-yl)-1-(2-thienyl)ethanolꢀ(11):ꢁ
+
1
35.5. HRMS (ESI-TOF). Calcd for C15
Found: m/z 308.08695.
H
15
N
3
OS [M+Na] : m/z 308.08280.
Yellow crystals; yield 240 mg; (88%); mp 115–118°C; H NMR: δ 7.79 (s,
1
1
1
1
H), 7.71–7.68 (m, 2H), 7.53–7.49 (m, 2H), 7.45–7.41 (m, 1H), 7.27–7.25 (m,
H), 7.02–7.00 (m, 1H), 6.98–6.96 (m, 1H), 5.38 (dd, J ꢀ= ꢀ 4.9 and 7.6 Hz,
13
H), 3.66 (bs, 1H), 3.34–3.31 (m, 2H); C NMR: δ 147.4, 145.0, 137.0, 129.7, Acknowledgments: We are grateful to the Yuzuncu Yil
28.7, 126.7, 124.6, 123.8, 120.5, 120.4, 69.3, 35.6. HRMS (ESI-TOF). Calcd
University, Scientific Research Projects Department (BAP
+
for C H N OS [M+H] : m/z 272.08521. Found: m/z 272.08854.
14
13
3
No. 2014-FBE-YL095).
4
-(4-(2-Hydroxy-2-(2-thienyl)ethyl)-1H-1,2,3-triazol-1-yl)phenol(12):ꢁ
1
Yellow crystals; yield 43 mg; (15%) mp 108–110°C; H NMR: δ 7.62 (s,
1
1
1
H), 7.27–7.25 (m, 3H), 6.99–6.95 (m, 4H), 5.39–5.37 (m, 1H), 5.06 (bs,
H), 2.99 (s, 2H) C NMR: δ 146.9, 144.1, 139.5, 129.3, 126.3, 124.3, 123.6,
References
1
3
20.0, 119.1, 106.9, 68.9, 35.1. HRMS (ESI-TOF). Calcd for C H N O S
14
13
3
2
[
1] Esvaran, S.; Adhikari, A. V.; Shetty, N. S. Synthesis and
antimicrobial activities of novel quinoline derivatives
carrying 1,2,4-triazole moiety. Eur. J. Med. Chem. 2009, 44,
+
[
M+H] : m/z 288.08012. Found: m/z 288.08223.
1
-(2-Thienyl)-2-(1-p-tolyl-1H-1,2,3-triazol-4-yl)ethanolꢀ(13):ꢁ
4637–4647.
1
Yellow crystals; yield 117 mg (41%); mp 119–121°C; H NMR: δ 7.74 (s,
[
2] Bayrak, H.; Demirbaş, A.; Demirbaş, N.; Karaoğlu, S. A.
Synthesis of some new 1,2,4-triazoles starting from isonicotinic
acid hydrazide and evaluation of their antimicrobial activities.
Eur. J. Med. Chem. 2009, 44, 4362–4366.
1
H), 7.57–7.54 (m, 2H), 7.30–7.27 (m, 2H), 7.25–7.24 (m, 1H), 7.00–6.99
(
(
1
m, 1H), 6.97–6.95 (m, 1H), 5.36 (dd, J ꢀ= ꢀ 4.9 and 7.4 Hz, 1H), 3.31–3.29
m, 2H); C NMR: δ 147.6, 144.8, 138.8, 134.7, 130.2, 126.7, 124.5, 123.7,
1
3
20.6, 120.3, 69.2, 35.6, 21.1. HRMS (ESI-TOF). Calcd for C H N OS [3] Kumar, S. S.; Kavitha, H. P. Synthesis and biological applications
1
5
15
3
+
[
M+H] : m/z 286.10092. Found: m/z 286.10281.
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