Microwave assisted synthesis of novel methylenebis{2-[(1-benzyl/cyclohexyl-1H-1,2,3-triazol-4-yl)methoxy]chalcones} and their antibacterial activity

Article abstract of DOI:10.1134/S1070363214080283

A series of novel methylenebis{2-[(1-benzyl/cyclohexyl-1H-1,2,3-triazol-4-yl)methoxy]chalcones} (IVa-IVn) have been synthesized by the Click reaction and Claisen-Schmidt condensation of 5,5'-methylenebis[2-(prop-2-yn-1-yloxy)benzaldehyde] under microwave irradiation with high yields. All products have been characterized by spectral data including FT-IR, ¹H, and ¹³C NMR, mass spectrometry, and tested for their antibacterial activity.

Full text of DOI:10.1134/S1070363214080283

ISSN 1070-3632, Russian Journal of General Chemistry, 2014, Vol. 84, No. 8, pp. 1608–1614. © Pleiades Publishing, Ltd., 2014.
Microwave Assisted Synthesis of Novel
Methylenebis{2-[(1-benzyl/cyclohexyl-1H-1,2,3-triazol-
4-yl)methoxy]chalcones}
and Their Antibacterial Activity1
S. Ramesh, D. Ashok , G. Linga Goud, and V. Prabhakar Reddy
Department of Chemistry, Osmania University, Hyderabad, 500007, India
e-mail: ashokdou@gmail.com
Received June 16, 2014
Abstract—A series of novel methylenebis{2-[(1-benzyl/cyclohexyl-1H-1,2,3-triazol-4-yl)methoxy]chalcones}
(IVa–IVn) have been synthesized by the Click reaction and Claisen-Schmidt condensation of 5,5'-
methylenebis[2-(prop-2-yn-1-yloxy)benzaldehyde] under microwave irradiation with high yields. All products
have been characterized by spectral data including FT-IR, 1H, and 13C NMR, mass spectrometry, and tested for
their antibacterial activity.
Keywords: antibacterial activity, bis-1,2,3-triazoles, chalcones, click chemistry, microwave irradiation
DOI: 10.1134/S1070363214080283
In the current study microwave irradiation was em-
ployed for reducing reaction time and improving yields
of reactions. Several reviews had been published on
various aspects of microwave-assisted chemistry [12].
Therefore we synthesized the title compounds under
microwave irradiation. Comparison of our data with
those accumulated for conventional thermal reactions
demonstrated the strong effect of microwave
irradiation on the reaction rate and made it possible to
shorten the reaction time and achieve high yields.
INTRODUCTION
1,2,3-Triazoles play an important role in organic
synthesis due to easy synthetic approach by the click
reaction, important properties as well as numerous
biological activities [1]. 1,2,3-Triazoles are highly
stable in basic and acidic media, under reductive and
oxidative conditions that indicate their aromatic
character [2]. 1,2,3-Triazoles participate in hydrogen
bonding, which is favorable in binding with
biomolecular targets [3]. 1,2,3-Triazole moiety is one
of the key structural units of a wide variety of
bioactive molecules that exhibit antifungal [4],
antibacterial [5], anti-HIV [6], antitubercular [7], anti-
inflammatory [8], anticancer [10], antioxidant and
antimicrobial [11] activities. 1,2,3-Triazole forms the
core structures in some well marketed drugs such as
tazobactam, cefatrizine, carboxyamidotriazole [9].
Chalcones are common natural pigments and they are
important intermediates in synthesis of a number of
heterocyclic compounds. Synthetic and naturally
occurring chalcones have been extensively studied and
developed as pharmaceutically important molecules.
Combination of 1,2,3-triazole and chalcone pharmaco-
phores can enhance their biological activity, which
prompted us to perform the synthesis of compounds
containing both 1,2,3--triazole and chalcone moieties.
RESULTS AND DISCUSSION
The synthetic route for titled compounds is
presented in Scheme 1. The compound I [13] reacted
with propargyl bromide in dry acetone in presence of
anhydrous K2CO3 and resulted in the propargylated
compound II. The latter reacted with benzyl azide or
cyclohexyl azide in presence of catalytic amount of
CuSO4·5H2O and sodium ascorbate in t-butylalcohol :
water (1 : 1) to give substituted triazoles IIIa or IIIb.
The process was carried out under microwave
irradiation and also by conventional method. The
compounds IIIa and IIIb reacted with aryl methyl
ketones in presence of KOH–alcohol under microwave
irradiation to give title compounds IVa–IVn with the
average yield 80–90%. We have carried out the same
reaction by conventional method that resulted in much
lower yield of the products.
1 The text was submitted by the authors in English.
1608

MICROWAVE ASSISTED SYNTHESIS
1609
Scheme 1.
CHO
1,3,5-trioxane,
H2SO4, acetic acid
OH
OH
HO
OH
reflux
OHC
I
CHO
CHO
HO
OH
propargyl bromide,
K2CO3, acetone
O
O
reflux
OHC
OHC
I
II
Benzyl/cyclohexyl azide
CuSO4· 5H2O
R5
N
ArCOCH3,
Ar
O
N
sodium ascorbate
N
KOH in EtOH
R5
N
N
R5
N
RT in t-butanol/Mw in DMF
RT/Mw
CHO
O
N
N
O
O
N
O
N
N
N
R5
Ar
OHC
O
IIIa, IIIb
IVa−IVn
R1
;
.
IVf : Ar =
Ar =
R4
S
R2
R3
IVa: R1 = H, R2 = H, R3 = OCH3, R4 = H, R5 = PhCH2; IVb: R1 = OH, R2 = H, R3 = CH3, R4 = Cl, R5 = PhCH2; IVc: R1 =
OH, R2 = H, R3 = H, R4 = Br, R5 = PhCH2; IVd: R1 = OH, R2 = H, R3 = H, R4 = F, R5 = PhCH2; IVe: R1 = OH, R2 = H, R3 =
H, R4 = H, R5 = PhCH2; IVg: R1 = OH, R2 = Cl, R3 = H, R4 = Cl, R5 = PhCH2; IVh: R1 = H, R2 = H, R3 = CH3, R4 = H, R5 =
PhCH2; IVi: R1 = H, R2 = H, R3 = H, R4 = H, R5 = PhCH2; IVj: R1 = OH, R2 = H, R3 = H, R4 = Br, R5 = C6H11; IVk: R1 =
OH, R2 = H, R3 = H, R4 = F, R5 = C6H11; IVl: R1 = OH, R2 = H, R3 = H, R4 = H, R5 = C6H11; IVm: R1 = OH, R2 = Cl, R3 = H,
R4 = Cl, R5 = C6H11; IVn: R1 = OH, R2 = H, R3 = CH3, R4 = Cl, R5 = C6H11.
Antibacterial activity. All compounds IVa–IVn
were tested for their antibacterial activity against
Escherichia coli and Staphylococcus aureus using
Ampicillin as a standard drug. The activity was studied
using cup plate agar diffusion method by measuring
the zone of inhibition in mm. Compounds IVb, IVc,
IVh, and IVn displayed inhibition potency against
both strains.
Melting points were measured in open capillary tubes.
The IR spectra were recorded as KBr pellets with a
1
Shimadzu FT-IR-8400s spectrophotometer. H NMR
(400 MHz) and 13C NMR (100 MHz) were measured
with Bruker Avance II 400 spectrometer using
tetramethylsilane as an internal standard in CDCl3 and
DMSO-d6 solutions. Mass spectra were measured with
a Hewlett-Packard 1100 LC/MSD spectrometer.
EXPERIMENTAL
Synthesis of 5,5'-methylenebis[2-(prop-2-yn-1-
yloxy)benzaldehyde] (II). A mixture of the solution
of I 5.0 g (10 mmol) in dry acetone (5 mL) in presence
of anhydrous K2CO3 and propargyl bromide 4.5 g
All chemicals were purchased from Aldrich and
Merk. All microwave reactions were carried out using
multiSynth series microwave oven system (Milestone).
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RAMESH et al.
Antibacterial data of target compounds
Zone of Inhibition, mm
Escherichia coli
Zone of Inhibition, mm
Compound
Staphylococcus aureus
25 µg/mL
50 µg/mL
14
100 µg/mL
25 µg/mL
50 µg/mL
100 µg/mL
IVa
IVb
IVc
12
18
9
20
25
16
15
16
23
22
18
18
16
19
21
19
23
25
6
8
7
6
6
5
4
4
2
7
3
7
4
7
9
8
10
10
7
9
13
12
9
22
12
IVd
IVe
8
11
10
16
16
11
12
11
13
17
15
19
20
15
6
7
IVf
18
6
6
IVg
IVh
IVi
17
4
5
15
6
9
15
4
5
IVj
14
9
13
6
IVk
IVl
17
3
19
9
10
7
IVm
IVn
Ampicillin
18
5
21
9
11
12
22
10
(20 mmol) was stirred and refluxed for 5 h. Progress of
the reaction was monitored by TLC. Upon completion
of the reaction, the solvent was evaporated and the
solid residue purified by column chromatography on
silica gel (60–120 mesh) with eluent hexane/EtOAc to
give compound II. IR spectrum (KBr), ν, cm–1: 1166
b. Microwave irradiation method. A mixture of 2.0 g
(6 mmol) of compound II, benzyl azide 1.7 g (12 mmol),
was treated with catalytic amount of CuSO4·5H2O and
sodium ascorbate in DMF under microwave irradiation
at 180 W for 6 min. Upon completion of the reaction
as indicated by TLC, the reaction mixture was poured
onto ice cold water and the residual solid was filtered
off, washed with water, and recrystallized from
ethanol. IR spectrum (KBr), ν, cm–1: 1160 (O–C), 1267
(Ar–O), 1556 (С=Сarom), 1567 (N=N), 1701 (С=O). 1Н
NMR spectrum (CDCl3), δ, ppm: 3.89 s (2H, ArCH2Ar),
5.28 s (4H, CH2Ph), 5.55 s (4H, OCH2), 7.14–7.44 m
(16Нarom), 7.55 s (2Нheteroarom), 10.37 s (2H, CHO). 13C
NMR spectrum (CDCl3), δ, ppm: 39.6, 54.3, 62.6,
113.4, 122.7, 124.9,128.1, 128.4, 128.9, 129.2, 133.6,
134.3, 136.3, 143.7, 159.1, 189.5 (C=O). MS (m/z):
599 [M + H]+.
1
(O–C), 1267 (Ar–O), 1560 (С=Сarom), 1710 (С=O). Н
NMR spectrum (CDCl3), δ, ppm: 2.57 s (2H, C≡CH),
3.93 s (2H, ArCH2Ar), 4.81 s (4H, OCH2), 7.04–7.67
m (6Нarom), 10.37 s (2H, CHO). 13C NMR spectrum
(CDCl3), δ, ppm: 38.9, 62.0, 80.1 (C≡C), 122.6, 123.2,
126.8, 128.4, 128.7, 128.9, 129.0, 130.0, 134.2, 134.6,
134.9, 157.9, 193.0 (C=O). MS (m/z): 332 [M + H]+.
5,5'-Methylenebis{2-[(1-benzyl-1H-1,2,3-triazol-
4-yl)methoxy]benzaldehyde} (IIIa). a. Conventional
method. A mixture of 2.0 g (6 mmol) of compound II,
benzyl azide 1.7 g (12 mmol), catalyticamount of
CuSO4·5H2O, and sodium ascorbate in t-butylalcohol :
water (1 : 1) was stirred for 24 h at room temperature.
Progress of the reaction was monitored by TLC. The
reaction mixture was poured over ice, the solid
obtained was filtered off, washed with water and
recrystallized from ethanol.
5,5'-Methylenebis{2-[(1-cyclohexyl-1H-1,2,3-tri-
azol-4-yl)methoxy]benzaldehyde} (IIIb). a. Conven-
tional method. A mixture of compound 2.0 g (6 mmol)
of compound II, cyclohexyl azide 1.5 g (12 mmol),
catalytic amount of CuSO4·5H2O, and sodium
ascorbate in t-butylalcohol : water (1 : 1) was stirred
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MICROWAVE ASSISTED SYNTHESIS
1611
for 24 h at RT. Progress of the reaction was monitored
by TLC. The reaction mixture was poured over ice, the
solid obtained was filtered, washed with water and
recrystallized from ethanol.
OCH2), 7.0–7.04 d (2Н, =CαH, J 15.5 Hz), 7.25–7.90
m (24Нarom), 7.91–7.95 d (2Н, =CβH, J 15.5 Hz), 8.32
s (2Нheteroarom). 13C NMR spectrum (CDCl3), δ, ppm:
30.6, 52.8 (ArOCH3), 55.2, 61.6, 113.3, 113.9, 122.0,
123.2, 124.8, 127.8, 128.0, 128.6, 129.2, 130.6, 132.0,
134.1, 135.9, 142.6, 155.5, 163.1, 187.3 (C=O). MS
(m/z): 863 [M + H]+. Found, %: C 73.74; H 5.35; N
9.76. C53H46N6O6. Calculated, %: C 73.76; H 5.37; N
9.74.
(2E,2'E)-3,3'-{Methylenebis[2-([1-benzyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-(5-
chloro-2-hydroxy-4-methylphenyl)prop-2-en-1-one]
(IVb). Yield 70% (method a) and 89% (method b), mp
188–190°С. IR spectrum (KBr), ν, cm–1: 1193 (O–C),
1263 (Ar–O), 1572 (N=N), 1582 (С=С), 1642 (С=O).
1Н NMR spectrum (CDCl3), δ, ppm: 2.38 s (6Н,
ArCH3), 3.97 s (2H, ArCH2Ar), 5.25 s (4H, CH2Ph),
5.61 s (4H, OCH2), 7.0–7.36 m (20Нarom), 7.92–7.96 d
(2Н, =CαH, J 15.6 Hz), 8.07-8.10 d (2Н, =CβH, J
15.6 Hz), 8.31 s (2Нheteroarom), 12.82 s (2H, OH). 13C
NMR spectrum (CDCl3), δ, ppm: 28.9 (ArCH3), 38.4,
55.2, 64.2, 98.5, 121.6, 123.4, 126.8, 128.0, 128.4,
128.7, 128.9, 130.2, 134.0, 134.2, 134.5, 142.6, 143.1,
155.4, 164.0, 198.6 (C=O). MS (m/z): 931 [M + H]+.
Found, %: C 68.26; H 4.67; N 9.20%. C51H44Cl2N6O6.
Calculated, %: C 68.31; H 4.76; N 9.02.
b. Microwave irradiation method. A mixture of
compound II 2.0 g (6 mmol), cyclohexyl azide 1.5 g
(12 mmol), catalytic amount of CuSO4·5H2O and
sodium ascorbate in DMF was subjected to react under
microwave irradiation at 180 W for 6 min. Upon
completion of the reaction as indicated by TLC, the
reaction mixture was poured onto ice cold water and
the solid that separated out was filtered, washed with
water, and recrystallized from ethanol. IR spectrum
(KBr), ν, cm–1: 1168 (O–C), 1260 (Ar–O), 1556
(С=Сarom), 1576 (N=N), 1705 (С=O). 1Н NMR
spectrum (CDCl3), δ, ppm: 1.44-2.25 m (22H, CH2–
CH2), 3.89 s (2H, ArCH2Ar), 5.30 s (4H, OCH2), 7.14–
7.44 m (16Нarom), 7.55 s (2Нheteroarom), 10.37 s (2H,
CHO). 13C NMR spectrum (CDCl3), δ, ppm: 38.2,
62.4, 112.4, 122.8, 123.6, 127.0, 128.4, 128.6, 128.9,
129.1, 130.2, 134.1, 134.6, 136.3, 143.0, 158.0, 190.5
(C=O). MS (m/z): 583 [M + H]+.
General synthesis of methylenebis{2-[(1-benzyl/
cyclohexyl-1H-1,2,3-triazol-4-yl)methoxy]chalcones}
(IVa–IVn). a. Conventional method. 0.16 mmol of a
compound IIIa or IIIb was condensed with 0.3 mmol
of an arylmethylketone under the action of KOH–
alcohol at room temperature. Progress of the reaction
which lasted for 12–14 h was monitored by TLC.
Upon completion of the process the reaction mixture
was poured onto ice cold water and the residual solid
product filtered off and purified with column
chromatography using mixture of petroleum ether and
ethyl acetate as an eluent.
(2E,2'E)-3,3'-{Methylenebis[2-([1-benzyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-(5-
bromo-2-hydroxyphenyl)prop-2-en-1-one] (IVc).
Yield 69% (method a) and 90% (method b), mp 155-
158°С. IR spectrum (KBr), ν, cm–1: 1183 (O–C), 1286
1
(Ar–O), 1567 (N=N), 1572 (С=С), 1640 (С=O). Н
NMR spectrum (CDCl3), δ, ppm: 3.96 s (2H,
ArCH2Ar), 5.24 s (4H, CH2Ph), 5.62 s (4H, OCH2),
7.33–7.37 d (2Н, =CαH, J 16 Hz), 7.25-7.98 m
(22Нarom), 8.04–8.08 d (2Н, =CβH, J 16 Hz), 8.30 s
(2Нheteroarom), 12.49 s (2H, OH). 13C NMR spectrum
(CDCl3), δ, ppm: 48.5, 52.8, 61.8, 110.2, 113.6, 120.0,
121.8, 122.8, 123.3, 124.7, 127.8, 128.0, 128.6, 132.2,
132.9, 134.0, 135.9, 138.0, 139.5, 142.6, 155.7, 160.0,
192.2 (C=O). MS (m/z): 991 [M + H]+. Found, %: C
61.68; H 4.02; N 8.48. C51H40Br2N6O6. Calculated, %:
C 61.76; H 4.06; N 8.47.
b. Microwave irradiation method. A solution of
0.16 mmol of a compound IIIa or IIIb and 0.3 mmol
of an arylmethylketone in ethanol was treated with
KOH under microwave irradiation at 320 W for 7–
9 min. The reaction mixture was poured onto ice cold
water and the residual solid product filtered off and
purified with column chromatography.
(2E,2'E)-3,3'-Dimethylenebis{2-[(1-benzyl-1H-
1,2,3-triazol-4-yl)methoxy]-5,1-phenylene)}bis[1-(4-
methoxyphenyl)prop-2-en-1-one] (IVa). Yield 69%
(method a) and 90% (method b), mp 164–166°С. IR
spectrum (KBr), ν, cm–1: 1169 (O–C), 1282 (Ar–O),
(2E,2'E)-3,3'-{Methylenebis[2-([1-benzyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-(5-
fluoro-2-hydroxyphenyl)prop-2-en-1-one] (IVd).
Yield 67% (method a) and 86% (method b), mp 70–
72°С. IR spectrum (KBr), ν, cm–1: 1178 (O–C), 1282
1
1575 (N=N), 1603 (С=С), 1651 (С=O). Н NMR
1
spectrum (CDCl3), δ, ppm: 3.31 s (6Н, ArOCH3), 3.93
(Ar–O), 1569 (N=N), 1578 (С=С), 1638 (С=O). Н
s (2H, ArCH2Ar), 5.25 s (4H, CH2Ph), 5.63 s (4H,
NMR spectrum (CDCl3), δ, ppm: 3.96 s (2H,
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 8 2014

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RAMESH et al.
ArCH2Ar), 5.24 s (4H, CH2Ph), 5.62 s (4H, OCH2),
7.65–7.69 d (2Н, =CαH, J 15.6 Hz), 7.02–7.59 m
(22Нarom), 8.03–8.07 d (2Н, =CβH, J 15.6 Hz), 8.30 s
(2Нheteroarom), 12.79 s (2H, OH). 13C NMR spectrum
(CDCl3), δ, ppm: 42.6, 54.4, 63.0, 97.8, 122.8, 123.2,
126.8, 128.0, 128.4, 128.7, 128.9, 130.2, 134.0, 134.2,
134.5, 142.6, 143.1, 154.4, 162.0, 197.2 (C=O). MS
(m/z): 871 [M + H]+. Found, %: C 70.31; H 4.64; N
9.63. C51H40F2N6O6. Calculated, %: C 70.34; H 4.63;
N 9.65.
NMR spectrum (CDCl3), δ, ppm: 3.96 s (2H,
ArCH2Ar), 5.29 s (4H, CH2Ph), 5.57 s (4H, OCH2),
7.14–7.44 m (20Нarom), 7.22–7.26 d (2Н, =CαH, J 15.6
Hz), 8.11-8.15 d (2Н, =CβH, J 15.6 Hz), 8.22 s
(2Нheteroarom), 13.48 s (2H, O–H). 13C NMR spectrum
(CDCl3), δ, ppm: 39.7, 54.3, 62.6, 113.1, 120.1, 121.1,
122.7, 123.1, 123.4, 123.9, 127.5, 128.1, 128.4, 128.9,
129.1, 130.7, 133.7, 134.3, 135.5, 143.0, 143.7, 156.7,
157.9, 193.0(C=O). MS (m/z): 971 [M + H]+. Found,
%: C 62.91; H 3.92; N 8.61. C51H38Cl4N6O6.
Calculated, %: C 62.97; H 3.94; N 8.64.
(2E,2'E)-3,3'-{Methylenebis[2-([1-benzyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-(2-
hydroxyphenyl)prop-2-en-1-one] (IVe). Yield 64%
(method a) and 83% (method b), mp 108–110°С. IR
spectrum (KBr), ν, cm–1: 1189 (O–C), 1287 (Ar–O),
(2E,2'E)-3,3'-{Methylenebis[2-([1-benzyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-(p-
tolyl)prop-2-en-1-one] (IVh). Yield 67% (method a)
and 86% (method b), mp 143–145°С. IR spectrum
(KBr), ν, cm–1: 1147 (O–C), 1279 (Ar–O), 1609
1
1556 (N=N), 1564 (С=С), 1642 (С=O). Н NMR
1
spectrum (CDCl3), δ, ppm: 3.96 s (2H, ArCH2Ar), 5.28
s (4H, CH2Ph), 5.57 s (4H, OCH2), 7.01-7.58 m
(24Нarom), 7.45–7.49 d (2Н, =CαH, J 15.5 Hz), 7.58 s
(2Нheteroarom), 8.03–8.07 d (2Н, =CβH, J 15.5 Hz), 12.91
s (2H, OH). 13C NMR spectrum (CDCl3), δ, ppm: 39.8,
54.3, 62.6, 113.0, 118.4, 118.8, 121.6, 122.8, 123.9,
128.0, 128.1, 128.9, 129.1, 129.8, 132.4, 133.8, 134.2,
136.2, 140.9, 143.9, 156.4, 163.5, 194.2 (C=O). MS
(m/z): 835 [M + H]+. Found, %: C 73.33; H 5.08; N
10.05. C51H42N6O6. Calculated, %: C 73.37; H 5.07; N
10.07.
(N=N), 1611 (С=С), 1651 (С=O). Н NMR spectrum
(CDCl3), δ, ppm: 2.37 s (6H, Ar–CH3), 3.92 s (2H,
ArCH2Ar), 5.24 s (4H, CH2Ph), 5.63 s (4H, OCH2),
7.20–7.95 m (24Нarom), 7.22–7.24 d (2Н, =CαH, J
10.8 Hz), 7.93–7.96 d (2Н, =CβH, J 10.8 Hz), 8.33 s
(2Нheteroarom). 13C NMR spectrum (CDCl3), δ, ppm:
21.1 (ArCH3), 39.0, 52.8, 61.7, 110.6, 123.1, 124.8,
127.8, 128.0, 128.4, 128.6, 129.2, 135.1, 135.9, 142.6,
143.4, 155.6, 195.3 (C=O). MS (m/z): 831 [M + H]+.
Found, %: C 76.57; H 5.56; N 10.16. C53H46N6O4.
Calculated, %: C 76.61; H 5.58; N 10.11.
(2E,2'E)-3,3'-{Methylenebis[2-([1-benzyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-
(thiophen-2-yl)prop-2-en-1-one] (IVf). Yield 60%
(method a) and 78% (method b), mp 126–128°С. IR
spectrum (KBr), ν, cm–1: 1124 (O–C), 1237 (Ar–O),
(2E,2'E)-3,3'-{Methylenebis[2-([1-benzyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-
phenylprop-2-en-1-one] (IVi). Yield 69% (method a)
and 84% (method b), mp 134–136°С. IR spectrum
(KBr), ν, cm–1: 1147 (O–C), 1276 (Ar–O), 1572
1
1
1564 (N=N), 1571 (С=С), 1640 (С=O). Н NMR
(N=N), 1602 (С=С), 1679 (С=O). Н NMR spectrum
spectrum (CDCl3), δ, ppm: 3.93 s (2H, ArCH2Ar), 5.25
s (4H, CH2Ph), 5.63 s (4H, OCH2), 7.22–8.03 m
(22Нarom), 7.84–7.86 d (2Н, =CαH, J 8.3 Hz), 8.02-8.03
d (2Н, =CβH, J 8.3 Hz), 8.32 s (2Нheteroarom). 13C NMR
spectrum (CDCl3), δ, ppm: 42.7, 54.2, 62.0, 98.6,
122.4, 123.2, 126.8, 128.0, 128.4, 128.7, 128.9, 130.2,
134.0, 134.2, 134.5, 142.6, 143.1, 155.4, 155.6, 194.2
(C=O). MS (m/z): 815 [M + H]+. Found, %: C 69.25; H
4.68; N 10.34; S 7.85. C47H38N6O4S2. Calculated, %: C
69.27; H 4.70; N 10.31; S 7.87.
(CDCl3), δ, ppm: 3.92 s (2H, ArCH2Ar), 5.27 s (4H,
CH2Ph), 5.52 s (4H, OCH2), 7.22–7.95 m (26Нarom),
7.18–7.22 d (2Н, =CαH, J 16 Hz), 7.98–8.02 d (2Н,
=CβH, J 16 Hz), 8.12 s (2Нheteroarom). 13C NMR
spectrum (CDCl3), δ, ppm: 43.2, 54.2, 62.6, 113.0,
122.8, 123.2, 124.2, 127.8, 128.5, 129.0, 129.9, 131.6,
134.6, 136.9, 138.3, 140.2, 144.1, 144.9, 153.4, 156.0,
190.9 (C=O). MS (m/z): 803 [M + H]+. Found, %: C
76.26; H 5.25; N 10.52. C51H42N6O4. Calculated, %: C
76.29; H 5.27; N 10.47.
(2E,2'E)-3,3'-{Methylenebis[2-([1-benzyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene[}bis[1-(3,5-
dichloro-2-hydroxyphenyl)prop-2-en-1-one] (IVg).
Yield 65% (method a) and 83% (method b), mp 171–
173°С. IR spectrum (KBr), ν, cm–1: 1124 (O–C), 1267
(2E,2'E)-3,3'-{Methylenebis(2-([1-cyclohexyl-
1H-1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis-
[1-(5-bromo-2-hydroxyphenyl)prop-2-en-1-one]
(IVj). Yield 70% (method a) and 90% (method b), mp
169–171°С. IR spectrum (KBr), ν, cm–1: 1183 (O–C),
1284 (Ar–O), 1576 (N=N), 1595 (С=С), 1638 (С=O).
1
(Ar–O), 1567 (N=N), 1577 (С=С), 1630 (С=O). Н
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 8 2014

MICROWAVE ASSISTED SYNTHESIS
1613
1
1Н NMR spectrum (CDCl3), δ, ppm: 1.25–2.20 m
(22H, CH2–CH2), 3.99 s (2H, ArCH2Ar), 5.32 s (4H,
OCH2), 7.48–7.66 m (12Нarom), 7.62–7.66 d (2Н,
=CαH, J 15.8 Hz), 8.17–8.21 d (2Н, =CβH, J 15.8 Hz),
7.68 s (2Нheteroarom), 12.82 s (2H, OH). 13C NMR spec-
trum (CDCl3), δ, ppm: 25.1, 29.7, 33.5, 39.8, 60.2,
63.0, 110.3, 113.4, 120.5, 121.4, 121.8, 123.7, 130.0,
131.9, 133.0, 133.7, 138.6, 138.8, 142.1, 143.0, 143.4,
156.6, 1557.6, 162.4, 193.2 (C=O). MS (m/z): 975
[M + H]+. Found, %: C 60.58; H 5.11; N 8.47.
C49H48Br2N6O6. Calculated, %: C 60.25; H 4.95; N
8.60.
(Ar–O), 1575 (N=N), 1567 (С=С), 1640 (С=O). Н
NMR spectrum (CDCl3), δ, ppm: 1.25–2.20 m (22H,
CH2–CH2), 3.98 s (2H, ArCH2Ar), 5.32 s (4H, OCH2),
7.65–7.69 d (2Н, =CαH, J 15.5 Hz), 7.48–7.66 m
(10Нarom), 7.67 s (2Нheteroarom), 8.17–8.21 d (2Н, =CβH,
J 15.5 Hz), 13.49 s (2H, OH). 13C NMR spectrum
(CDCl3), δ, ppm: 25.1, 29.7, 33.5, 39.2, 60.3, 62.9,
113.4, 120.5, 123.1, 123.5, 127.5, 130.5, 133.3, 133.7,
135.5, 142.8, 143.1, 156.8, 157.9, 193.1 (C=O). MS
(m/z): 955 [M + H]+. Found, %: C 61.84; H 4.96; N
8.70. C49H46Cl4N6O6. Calculated, %: C 61.51; H 4.85;
N 8.76.
(2E,2'E)-3,3'-{Methylenebis[2-([1-cyclohexyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-(5-
chloro-2-hydroxy-4-methylphenyl)prop-2-en-1-one]
(IVn). Yield 70% (method a) and 89% (method b), mp
201–203°С. IR spectrum (KBr), ν, cm–1: 1185 (O–C),
1280 (Ar–O), 1560 (N=N), 1586 (С=С), 1638 (С=O).
1Н NMR spectrum (CDCl3), δ, ppm: 1.25–2.20 m
(22H, CH2–CH2), 2.38 s (6H, ArCH3), 3.94 s (2H,
ArCH2Ar), 5.32 s (4H, OCH2), 7.61–7.65 d (2Н,
=CαH, J 15.5 Hz), 7.48–7.66 m (10Нarom), 7.67 s
(2Нheteroarom), 8.14–8.18 d (2Н, =CβH, J 15.5 Hz), 12.78
s (2H, OH). 13C NMR spectrum (CDCl3), δ, ppm: 25.1
(ArCH3), 33.5,60.2, 63.1, 113.4, 119.1, 120.5, 123.8,
124.0, 129.2, 130.1, 132.8, 133.7, 141.4, 143.1, 145.3,
156.5, 161.9, 192.9(C=O). MS (m/z): 915 [M + H]+.
Found %: C 66.12; H 5.78; N 9.16. C51H52Cl2N6O6.
Calculated, %: C 66.88; H 5.72; N 9.18.
(2E,2'E)-3,3'-{Methylenebis[2-([1-cyclohexyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-(5-
fluoro-2-hydroxyphenyl)prop-2-en-1-on] (IVk).
Yield 65% (method a) and 84% (method b), mp 72–
75°С. IR spectrum (KBr), ν, cm–1: 1183 (O–C), 1286
1
(Ar–O), 1567 (N=N), 1592 (С=С), 1638 (С=O). Н
NMR spectrum (CDCl3), δ, ppm: 1.25–2.20 m (22H,
CH2–CH2), 3.86 s (2H, ArCH2Ar), 5.30 s (4H, OCH2),
7.12–7.14 d (2Н, =CαH, J 16 Hz), 7.48-7.66 m
(12Нarom), 7.62–7.64 d (2Н, =CβH, J 16 Hz), 8.11 s
(2Нheteroarom), 12.69 s (2H, OH). 13C NMR spectrum
(CDCl3), δ, ppm: 25.4, 29.7, 33.4, 42.5, 60.2, 62.4,
118.2, 119.4, 133.0, 143.0, 155.0, 158.6, 204.4 (C=O).
MS (m/z): 855 [M + H]+. Found, %: C 69.09; H 5.63;
N 9.65. C49H48F2N6O6. Calculated, %: C 68.84; H
5.66; N 9.83.
(2E,2'E)-3,3'-{Methylenebis[2-([1-cyclohexyl-1H-
1,2,3-triazol-4-yl]methoxy)-5,1-phenylene]}bis[1-(2-
hydroxyphenyl)prop-2-en-1-one] (IVl). Yield 66%
(method a) and 87% (method b), mp 83–85°С. IR
spectrum (KBr), ν, cm–1: 1185 (O–C), 1276 (Ar–O),
ACKNOWLEDGMENTS
Authors are grateful to The Head, Department of
Chemistry, and Director, Central Facilities for Research
and Development (CFRD), Osmania University,
Hyderabad for providing laboratory facilities and
spectra. One of the authors S.R is grateful to UGC,
New Delhi for awarding JRF.
1
1568 (N=N), 1596 (С=С), 1640 (С=O). Н NMR
spectrum (CDCl3), δ, ppm: 1.25–2.20 m (22H, CH2–
CH2), 3.73 s (2H, ArCH2Ar), 5.19 s (4H, OCH2), 7.40–
7.43 d (2Н, =CαH, J 10.0 Hz), 7.48–7.66 m (14Нarom),
7.57 s (2Нheteroarom), 7.79-7.82 d (2Н, =CβH, J 10.0 Hz),
12.2 s (2H, OH). 13C NMR spectrum (CDCl3), δ, ppm:
25.0, 29.7, 33.4, 42.6, 60.2, 62.6, 118.3, 118.9, 119.0,
130.2, 136.3, 143.7, 154.1, 162.4, 205.3 (C=O). MS
(m/z): 819 [M + H]+. Found, %: C 71.11; H 6.26; N
10.12. C49H50N6O6. Calculated, %: C 71.86; H 6.15; N
10.26.
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