Ultrasound- and microwave-assisted synthesis of (E)-1-aryl-3-[2-(piperidin- 1-yl)quinolin-3-yl]prop-2-en-1-ones and (E)-1-aryl-3-[2-(pyrrolidin-1-yl) quinolin-3-yl]prop-2-en-1-ones, and their antimicrobial activity

Article abstract of DOI:10.1134/S1070363214060309

Series of new (E)-1-aryl-3-[2-(piperidin-1-yl)quinolin-3-yl]prop-2-en-1- ones and (E)-1-aryl-3-[2-(pyrrolidin-1-yl)quinolin-3-yl]prop-2-en-1-ones have been efficiently prepared via the Claisen-Schmidt condensation of 2-(piperidin-1-yl)quinoline-3-carbalde

Full text of DOI:10.1134/S1070363214060309

ISSN 1070-3632, Russian Journal of General Chemistry, 2014, Vol. 84, No. 6, pp. 1237–1242. © Pleiades Publishing, Ltd., 2014.
Ultrasound- and Microwave-Assisted Synthesis
of (E)-1-Aryl-3-[2-(piperidin-1-yl)quinolin-3-yl]prop-2-en-1-ones
and (E)-1-Aryl-3-[2-(pyrrolidin-1-yl)quinolin-3-yl]prop-2-en-1-ones,
and Their Antimicrobial Activity1
D. Ashok, Arram Ganesh, B. Vijaya Lakshmi, and S. Ravi
Department of Chemistry, Osmania University, Hyderabad-500 007, India
e-mail: ashokdou@gmail.com
Received March 28, 2014
Abstract—Series of new (E)-1-aryl-3-[2-(piperidin-1-yl)quinolin-3-yl]prop-2-en-1-ones and (E)-1-aryl-3-[2-
(pyrrolidin-1-yl)quinolin-3-yl]prop-2-en-1-ones have been efficiently prepared via the Claisen-Schmidt
condensation of 2-(piperidin-1-yl)quinoline-3-carbaldehyde and 2-(pyrrolidin-1-yl)quinoline-3-carbaldehyde,
respectively, with aryl methyl ketones under conditions of ultrasound and microwave irradiation. Structures of
the products have been confirmed by IR, 1H NMR, 13C NMR, and mass spectroscopy, as well as by elemental
analysis. Evaluation of the in vitro antibacterial activity against bacterial (Gram-positive Staphylococcus aureus
and Gram-negative Escherichia coli) and fungal (Aspergillus niger and Candida metapsilosis) strains has
revealed good antimicrobial activity of some of the tested compounds.
Keywords: ultrasound-assisted synthesis, microwave-assisted synthesis, antimicrobial activity
DOI: 10.1134/S1070363214060309
Quinoline and its derivatives represent a vast class
of heterocycles that are found in many natural products
and drugs [see example (a) in Scheme 1] and are of
significant importance in medicinal applications.
Several quinoline derivatives have been reported to
exhibit various biological activities: antibacterial [1],
antimalarial [2], antiallergenic [3], antiinflammatory
[4], and antitumor [5]. Among the quinolines, 2-
chloro-3-formylquinolines are of special importance
for organic synthesis as key intermediates for further
β-annelation of various ring systems and intercon-
version of many functional groups [6]. Piperidine
derivatives are known as active pharmacological
agents as well: antimicrobial [7], anticonvulsant [8],
antiinflammatory [9], antidepressant (Paroxetine), and
attention-deficit hyperactivity disorder (ADHD)
[Methylphenidate, example (b) in Scheme 1] drugs.
Pharmacological activity of pyrrolidines is versatile as
well: they reveal antimicrobial [10], antitumor [10],
anti-HIV [11], and anticonvulsant [12] activity.
Chalcones form another important class of structures
showing antimicrobial [13], anti-inflammatory [14],
and anticancer [15] activity. For instance, Sofalcone
[example (c) in Scheme 1] is a gastroprotective
chalcone-based drug promoting healing of gastric ulcer
and inhibiting some types of enzymes. Chalcones
constitute an important class of natural products
belonging to the flavonoid family [16] which are key
precursors in synthesis of many biologically important
heterocycles such as benzothiazepines [17], pyra-
zolines [18], 1,4-diketones [19], and flavones [20].
Preparation of chalcones has been therefore of
emerging interest among organic as well as medicinal
chemists (Scheme 1).
Microwave-assisted organic reaction enhancement
(MORE) is nowadays a well established technique for
synthesis of various heterocycles. Virtually any
thermally driven reaction can be accelerated by
microwave irradiation. The spectacular results (shorter
reaction time, experimental simplicity, and selectivity)
have clearly indicated the advantages of this technique
over conventional heating. Similarly, the advantages of
ultrasound-assisted synthesis include higher yields,
shorter reaction times, and milder reaction conditions
as compared with conventional methods. Our research
group has made considerable efforts to design and put
into practice innovative synthetic protocols adopting a
more eco-sustainable approach [21]. As a part of our
1 The text was submitted by the authors in English.
1237

1238
D. ASHOK et al.
Scheme 1.
NH
O
O
O
O
H
N
O
O
O
N
HO
Viqualine
Methylphenidate
Sofalcone
(a) Quinoline-based drug (b) Piperidine-based drug
(c) Chalcone-based drug
Scheme 2.
O
N
O
5
8
4
O
3
2
6
7
H
Ar
KOH
+
Ar
CH3
MWI or
ultrasound
N
N
1
N
I
IIa−IIi
IIIa−IIIi
Ar = a: phenyl, b: 4-methylphenyl, c: 4-methoxyphenyl, d: 4-chlorophenyl, e: 4-bromophenyl, f: 4-nitrophenyl, g: 2-naphthyl,
h: 1-naphthyl, i: thienyl.
Scheme 3.
O
N
O
O
5
4
3
KOH
6
7
H
Ar
Ar
CH3
MWI or
ultrasound
N
N
1
N
2
8
IV
IIa−IIg
Va−Vg
Ar = a: phenyl, b: 4-methylphenyl, c: 4-methoxyphenyl, d: 4-chlorophenyl, e: 4-bromophenyl, f: 4-nitrophenyl, g: 1-naphthyl.
research program, herein we report on preparation of
new (E)-1-aryl-3-[2-(piperidin-1-yl)quinolin-3-yl]prop-
2-en-1-ones and (E)-1-aryl-3-[2-(pyrrolidin-1-yl)quino-
lin-3-yl]prop-2-en-1-ones via conventional and non-
drug. The prepared compounds IIIa, IIIe, Va, Vf, and
Vg showed good antibacterial activity against all the
tested organisms. Screening of antifungal activity of
the prepared products (against Aspergillus niger and
conventional (ultrasound- and microwave-assisted) Candida metapsilosis using grieseofulvin as standard
methods. Structures of the prepared products are shown
in the Schemes 2, 3; syntheses conditions are tabulated
along with the observed melting points; results from
other characterization methods are to be found in the
Experimental.
drug) revealed that the products IIIa, IIId, Vf, and Vg
showed good antifungal activity against all the tested
organisms.
EXPERIMENTAL
Melting points were determined in open capillary
tubes and are uncorrected. Purity of the compounds
was checked by TLC using precoated silica gel plates
All the compounds were screened for their
antibacterial activity against Escherichia coli and
Staphylococcus aureus using ampicillin as a reference
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ULTRASOUND- AND MICROWAVE-ASSISTED SYNTHESIS
1239
Preparation conditions of (E)-1-aryl-3-[2-(piperidin-1-yl)quinolin-3-yl]prop-2-en-1-ones (IIIa–IIIi) and (E)-1-aryl-3-[2-(pyrrolidin-
1-yl)quinolin-3-yl]prop-2-en-1-ones (Va–Vg) and the products melting points
Reaction time
Yield, %
Product no.
mp, °C
conventional, h
USIa, min
45
MWIb, min conventional, h
USIa
82
84
84
80
79
83
80
78
80
83
81
82
80
80
82
80
MWIb
88
90
92
86
87
86
90
88
90
90
89
90
88
88
90
86
IIIa
IIIb
IIIc
IIId
IIIe
IIIf
IIIg
IIIh
IIIi
Va
142
102
128
136
120
192
186
132
172
133
119
126
151
163
115
107
5.0
5.5
5.0
6.0
6.0
6.0
6.0
6.0
5.0
6.0
5.5
5.0
6.0
5.5
5.0
6.0
3.0
3.5
3.5
4.0
3.5
4.0
4.0
4.0
3.0
4.0
3.5
3.5
4.0
4.0
3.5
4.0
70
71
72
66
68
70
72
70
74
72
69
72
66
66
72
74
40
40
45
45
50
40
40
40
40
Vb
35
Vc
35
Vd
40
Ve
40
Vf
40
Vg
40
a Ultrasound irradiation. b Microwave irradiation.
60254 (Merck). Microwave reactions were carried out
in the milestone multi SYNTH microwave system.
Sonication was performed in Shanghai BUG40-06
ultrasonic cleaner (with a frequency of 25 kHz, 40 kHz,
59 kHz and a nominal power of 250 W). IR (KBr)
spectra were recorded on a Shimadzu FT-IR-8400s
Preparation of (E)-1-aryl-3-[2-(piperidin-1-yl)
quinolin-3-yl]prop-2-en-1-ones (IIIa–IIIi) and (E)-
1-aryl-3-[2-(pyrrolidin-1-yl)quinolin-3-yl]prop-2-en-
1-ones (Va–Vg) (general procedures). Conventional
method. A mixture of 2-piperidin- (I) or 2-pyrrolidin-
1-yl-quinoline-3-carbaldehyde (IV) (1 mmol), aryl
methyl ketone (IIa–IIi) (1 mmol), and potassium
hydroxide (3 mmol) was dissolved in ethanol (10 mL)
and stirred at room temperature. The reaction progress
was monitored by TLC; after completion of the
reaction, the reaction mixture was poured into ice
water and neutralized with diluted HCl solution. The
separated solid was filtered off, washed with water,
dried, and purified by column chromatography using
(silica gel, eluent: hexane:ethyl acetate, 10 : 1, v/v) to
yield the pure compounds IIIa–IIIi and Va–Vg.
1
spectrophotometer. H NMR and 13C NMR spectra
were recorded using the Bruker Avance II 400 MHz
instrument with tetramethylsilane as an internal
reference. Mass spectra were recorded using the CMS-
QP 1000 EX mass spectrometer. Elemental analysis was
determined with the Thermo Finnigan CHNS analyzer.
Antifungal activity evaluation. Antifungal activity
of the products was tested against Aspergillus niger
and Candida metapsilosis with grieseofulvin as a
reference drug. The activity was determined using cup
plate agar diffusion method by measuring the zone of
inhibition in mm. The compounds were screened at
concentration of 100 μg/mL in DMSO.
Ultrasound-assisted method. A mixture of 2-
piperidin- (I) or 2-pyrrolidin-1-yl-quinoline-3-carbal-
dehyde (IV) (1 mmol), aryl methyl ketone (IIa–IIi)
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 84 No. 6 2014

1240
D. ASHOK et al.
(1 mmol), and potassium hydroxide (3 mmol) was
dissolved in ethanol (20 mL). The solution was then
subject to ultrasound irradiation during 40–50 min. at
60°C. The reaction progress was monitored by TLC;
after completion of the reaction, the reaction mixture
was poured into ice water and neutralized with diluted
HCl solution. The separated solid was filtered off,
washed with water, dried, and purified by column
chromatography using (silica gel, eluent – hexane :
ethyl acetate, 10 : 1, v/v) to yield the pure compounds
IIIa–IIIi and Va–Vg.
IIIc. IR spectrum, ν, cm–1: 1595 (C=C), 1660
(C=O), 2924 (C–H). 1H NMR spectrum, δ, ppm: 1.65–
1.68 t (2H, –CH2–), 1.76–1.80 q (4H, 2XN–CH2–CH2–),
3.34–3.37 t (4H, 2XN–CH2–), 3.91 s (3H, OCH3),
7.01–7.03 d (2H, ArH), 7.33–7.37 t (1H, C6–H), 7.59–
7.73 m (3H, C7–H, C8–H, and Hα), 7.82–7.85 d (1H,
C5–H), 7.98–8.02 d (1H, Hβ), 8.09–8.11 d (2H, ArH),
13
8.24 s (1H, C4–H). C NMR spectrum, δC, ppm: 24.6,
26.1, 51.8, 55.5, 113.8, 122.4, 123.4, 124.2, 124.7,
127.4, 127.7, 130.3, 131.0, 136.8, 141.7, 147.8, 160.8,
188.6. Found, %: C 77.39; H 6.49; N 7.52.
C24H24N2O2. Calculated, %: C 77.34; H 6.51; N 7.48.
M 373 [M + H]+.
Microwave-assisted method. A mixture of 2-
piperidin- (I) or 2-pyrrolidin-1-yl-quinoline-3-carbal-
dehyde (IV) (1 mmol), aryl methyl ketone (IIa–IIi)
(1 mmol), and potassium hydroxide (3 mmol) was
dissolved in ethanol (5 mL) and subject to periodic
microwave irradiation at 160 W (3–4 min at 30 s
intervals). The reaction progress was monitored by
TLC; after completion of the reaction, the reaction
mixture was poured into ice water and neutralized with
diluted HCl solution. The separated solid was filtered
off, washed with water, dried, and purified by column
chromatography using (silica gel, eluent – hexane :
ethyl acetate, 10 : 1, v/v) to yield the pure compounds
IIIa–IIIi and Va–Vg.
IIId. IR spectrum, ν, cm–1: 1593 (C=C), 1658
(C=O), 2927 (C–H). 1H NMR spectrum, δ, ppm: 1.66–
1.68 t (2H, –CH2–), 1.76–1.79 q (4H, 2XN–CH2–CH2–),
3.33–3.36 t (4H, 2XN–CH2–), 7.34–7.38 t (1H, C6–H),
7.50–7.52 d (2H, ArH), 7.61–7.63 m (3H, C7–H, C8–H,
and Hα), 7.83–7.85 d (1H, C5–H), 8.00–8.04 m (3H,
ArH, and Hβ), 8.24 s (1H, C4–H). 13C NMR spectrum,
δC, ppm: 24.6, 26.1, 51.8, 121.9, 122.9, 124.3, 124.7,
127.4, 127.7, 129.0, 129.9, 130.5, 136.4, 137.1, 139.3,
143.1, 147.9, 160.7, 189.1. Found, %: C, 73.30; H
5.62; N 7.43. C23H21ClN2O. Calculated, %: C, 73.26;
H 5.65; N 7.40. M 377 [M + H]+.
IIIa. IR spectrum, ν, cm–1: 1593 (C=C), 1654
(C=O), 3059 (C–H). 1H NMR spectrum, δ, ppm: 1.66–
1.67 t (2H, –CH2–), 1.75–1.79 m (4H, 2XN–CH2–
CH2–), 3.34–3.37 t (4H, 2XN–CH2–), 7.34–7.38 t (1H,
C6–H), 7.52–7.64 m (4H, C7–H and ArH), 7.67–7.74
m (2H, C8–H and Hα), 7.83–7.85 d (1H, C5–H), 7.99–
8.03 d (1H, Hβ), 8.06–8.08 d (2H, ArH), 8.25 s (1H,
C4–H). 13C NMR spectrum, δC, ppm: 24.6, 26.1, 51.8,
123.1, 123.6, 124.3, 124.6, 127.3, 127.6, 128.8, 129.4,
131.1, 132.6, 134.9, 142.2, 142.9, 148.1, 160.8, 189.2.
Found, %: C 80.67; H 6.48; N 8.18. C23H22N2O.
Calculated, %: C 80.61; H 6.52; N 8.14. M 343
[M + H]+.
IIIb. IR spectrum, ν, cm–1: 1585 (C=C), 1654
(C=O), 2933 (C–H). 1H NMR spectrum, δ, ppm: 1.66–
1.67 t (2H, –CH2–), 1.75–1.80 q (4H, 2XN–CH2–CH2–),
2.46 s (3H, CH3), 3.34–3.37 t (4H, 2XN–CH2–), 7.32–
7.37 m (3H, C6–H and ArH), 7.59–7.73 m (3H, C7–H,
C8–H, and Hα), 7.82–7.84 d (1H, C5–H), 7.98–8.02 m
(3H, ArH and Hβ), 8.25 s (1H, C4–H). 13C NMR
spectrum, δC, ppm: 21.7, 24.6, 26.0, 51.8, 122.6, 123.3,
124.3, 124.7, 127.4, 127.8, 128.7, 129.4, 130.3, 135.5,
136.9, 142.2, 143.7, 147.8, 160.7, 189. Found, %: C
80.87; H 6.79; N 7.86. C24H24N2O. Calculated, %: C
80.81; H 6.73; N 7.88. M 357 [M + H]+.
IIIe. IR spectrum, ν, cm–1: 1591 (C=C), 1658
(C=O), 2926 (C–H). 1H NMR spectrum, δ, ppm: 1.65–
1.69 t (2H, –CH2–), 1.75–1.81 q (4H, 2XN–CH2–CH2–),
3.34–3.36 t (4H, 2XN–CH2–), 7.33–7.38 t (1H, C6–H),
7.61–7.74 m (5H, C7–H, C8–H, Hα, and ArH), 7.83–
7.85 d (1H, C5–H), 7.93–7.95 d (2H, ArH), 8.01–8.04
d (1H, Hβ), 8.25 s (1H, C4–H). 13C NMR spectrum, δC,
ppm: 24.6, 26.1, 51.8, 121.9, 122.9, 124.6, 127.5,
127.8, 129.9, 130.5, 131.5, 131.9, 136.8, 137.1, 143.2,
147.9, 160.7, 189.3. Found, %: C, 65.57; H 5.02; N
6.65. C23H21BrN2O. Calculated, %: C, 65.52; H 5.06;
N 6.69. M 421[M + H]+.
IIIf. IR spectrum, ν, cm–1: 1583 (C=C), 1664
1
(C=O), 2920 (C–H). H NMR spectrum, δ, ppm: δ
1.67–1.68 t (2H, –CH2–), 1.75–1.81 q (4H, 2XN–CH2–
CH2–), 3.33–3.36 t (4H, 2XN–CH2–), 7.27–7.37 d
(2H, ArH), 7.63–7.84 m (4H, C6–H, C7–H, C8–H, and
Hα), 7.93–7.95 d (2H, ArH), 8.03–8.28 m (2H, C5–H
and Hβ), 8.38 s (1H, C4–H). 13C NMR spectrum, δC,
ppm: 24.5, 26.0, 51.9, 121.7, 122.4, 123.9, 124.5,
124.6, 127.6, 127.9, 129.4, 130.8, 137.4, 142.9, 144.6,
148.1, 150.1, 160.7, 189.0. Found, %: C, 71.30; H
5.46; N 10.85. C23H21N3O3. Calculated, %: C 71.24; H
5.51; N 10.80. M 388 [M + H]+.
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ULTRASOUND- AND MICROWAVE-ASSISTED SYNTHESIS
1241
IIIg. IR spectrum, ν, cm–1: 1583 (C=C), 1654
(C=O), 2927 (C–H). 1H NMR spectrum, δ, ppm: 1.65–
1.68 t (2H, –CH2–), 1.78–1.81 q (4H, 2XN–CH2–CH2–),
3.36–3.39 t (4H, 2XN–CH2–), 7.35–7.39 t (1H, C6–H),
7.59–7.65 m (3H, C7–H, C8–H, and Hα ), 7.75–7.77 d
(1H, C5–H), 7.84–8.04 m (5H, ArH), 8.07–8.11 d (1H,
Hβ), 8.15–8.17 d (1H, ArH), 8.31 s (1H, C4–H), 8.61 s
(1H, ArH). 13C NMR spectrum, δC, ppm: 24.5, 26.0,
51.8, 122.5, 123.2, 124.3, 124.5, 124.7, 126.8, 127.5,
127.8, 127.9, 128.4, 128.7, 129.6, 130.0, 130.4, 135.4,
135.6, 137.0, 142.5, 147.9, 160.8, 190.2. Found, %: C
82.62; H 6.16; N 7.14. C27H24N2O. Calculated, %: C
82.56; H 6.22; N 7.17. M 393 [M + H]+.
IIIh. IR spectrum, ν, cm–1: 1582 (C=C), 1657
(C=O), 2932 (C–H). 1H NMR spectrum, δ, ppm: 1.52–
1.55 t (2H, –CH2–), 1.61–1.64 p (4H, 2XN–CH2–CH2–),
3.23–3.26 t (4H, 2XN–CH2–), 7.35–7.42 m (2H, C6–H
and ArH), 7.51–7.82 m (6H, C5–H, C7–H, C8–H, Hα,
and ArH), 7.87–8.07 m (5H, ArH, and Hβ), 8.24 s (1H,
C4–H). 13C NMR spectrum, δC, ppm: 24.6, 26.0, 51.7,
120.5, 122.2, 122.9, 124.6, 124.8, 126.8, 127.4,
127.87, 127.9, 128.0, 128.4, 129.2, 130.4, 131.6,
135.5, 143.1, 146.9, 160.7, 190.1. Found, %: C 82.59;
H 6.19; N 7.26. C27H24N2O. Calculated, %: C 82.56; H
6.22; N 7.17. M 393 [M + H]+.
1.96 m (4H, 2X–CH2–), 2.45 s (3H, CH3), 3.69–3.72 t
(4H, 2XN–CH2–), 7.21–7.24 m (1H, C6–H), 7.32–7.34
d (2H, ArH), 7.45–7.49 d (1H, Hα), 7.53–7.57 m (1H,
C7–H), 7.63–7.66 d (1H, C8–H), 7.71–7.73 d (1H,
C5–H), 7.98–8.00 d (2H, ArH), 8.10 s (1H, C4–H),
8.15–8.19 d (1H, Hβ), 13C NMR spectrum, δC, ppm:
21.7, 25.8, 50.7, 121.1, 122.4, 122.6, 123.3, 126.5,
127.7, 128.7, 129.4, 130.5, 135.4, 137.0, 143.8, 148.3,
156.7, 189.3. Found, %: C 80.67; H 6.48; N 8.18.
C23H22N2O. Calculated, %: C 80.67; H 6.48; N 8.18. M
343 [M + H]+.
Vc. IR spectrum, ν, cm–1: 1585 (C=C), 1655 (C=O),
1
2962 (C–H). H NMR spectrum, δ, ppm: 1.93–1.96 m
(4H, 2X–CH2–), 3.69–3.72 t (4H, 2XN–CH2–), 3.91 s
(3H, OCH3), 7.00–7.02 t (1H, C6–H), 7.21–7.24 d (2H,
ArH), 7.46–7.50 d (1H, Hα), 7.53–7.57 m (1H, C7–H),
7.64–7.66
d
(1H, C8–H), 7.71–7.73
d
(1H,
C5–H), 8.08–8.10 m (3H, ArH and C4–H), 8.15–8.19 d
(1H, Hβ). 13C NMR spectrum, δC, ppm: 25.8, 50.7,
55.5, 113.9, 121.2, 122.2, 122.6, 123.3, 126.5, 127.7,
130.2, 130.9, 136.9, 143.4, 148.3, 156.7, 163.5, 188.0.
Found, %: C 77.07; H 6.19; N 7.82. C23H22N2O2.
Calculated, %: C 77.07; H 6.19; N 7.82. M 359
[M + H]+.
Vd. IR spectrum, ν, cm–1: 1579 (C=C), 1654
(C=O), 2964 (C–H). 1H NMR spectrum, δ, ppm: 1.91–
1.95 m (4H, 2X–CH2–), 3.70–3.76 t (4H, 2XN–CH2–),
7.21–7.23 t (1H, C6–H), 7.41–7.73 m (5H, C7–H,
C8–H, Hα , and ArH), 7.92–7.94 d (1H, C5–H), 8.01–
8.03 d (2H, ArH), 8.11 s (1H, C4–H), 8.18–8.22 d (1H,
Hβ). 13C NMR spectrum, δC, ppm: 25.2, 50.8, 120.8,
121.4, 122.7, 122.9, 123.3, 124.2, 127.4, 132.2, 132.7,
135.5, 141.2, 146.3, 154.2, 188.8. Found, %: C 72.82;
H 5.28; N 7.72. C22H19ClN2O. Calculated, %: C 72.82;
H 5.28; N 7.72. M 363 [M + H]+.
IIIi. IR spectrum, ν, cm–1: 1591 (C=C), 1658
(C=O), 2926 (C–H). 1H NMR spectrum, δ, ppm: 1.65–
1.69 t (2H, –CH2–), 1.75–1.81 q (4H, 2XN–CH2–CH2–),
3.33–3.36 t (4H, 2XN–CH2–), 7.22–7.24 t (1H,
ArH),7.39–7.42 m (1H, C6–H), 7.59–7.78 m (5H,
C7–H, C8–H, Hα, and ArH), 7.86–7.88 d (1H, C5–H),
8.05–8.08 d (1H, Hβ), 8.15 s (1H, C4–H). 13C NMR
spectrum, δC, ppm: 24.6, 26.1, 51.8, 121.9, 122.9,
124.6, 127.5, 127.8, 129.9, 130.5, 131.5, 131.9, 136.8,
137.1, 143.2, 147.9, 160.7, 189.3. Found, %: C 72.38;
H 5.79; N 8.04; S, 9.20. C21H20N2OS. Calculated, %: C
72.32; H 5.84; N 8.09; S, 9.15. M 349 [M + H]+.
Va. IR spectrum, ν, cm–1: 1571 (C=C), 1654
(C=O), 2960 (C–H). 1H NMR spectrum, δ, ppm: 1.93–
1.96 m (4H, 2X–CH2–), 3.69–3.72 t (4H, 2XN–CH2–),
7.21–7.25 t (1H, C6–H), 7.46–7.66 m (5H, C7–H, C7–
H, Hα, and ArH), 7.71–7.73 d (1H, C5–H), 8.06–8.11
m (3H, ArH and C4–H), 8.17–8.21 d (1H, Hβ), 13C
NMR spectrum, δC, ppm: 25.8, 50.8, 121.0, 122.3,
122.6, 123.3, 126.5, 127.7, 128.2, 128.5, 130.5, 132.9,
137.1, 137.9, 144.3, 148.4, 156.7, 189.9. Found, %: C
80.46; H 6.14; N 8.53. C22H20N2O. Calculated, %: C
80.46; H 6.14; N 8.53. M 329[M + H]+.
Ve. IR spectrum, ν, cm–1: 1587 (C=C), 1656 (C=O),
1
2964 (C–H). H NMR spectrum, δ, ppm: 1.93–1.96 m
(4H, 2X–CH2–), 3.68–3.71 t (4H, 2XN–CH2–), 7.21–
7.25 m (1H, C6–H), 7.46–7.64 m (5H, m, 5H, C7–H,
C8–H, Hα , and ArH), 7.73–7.75 d (1H, C5–H), 8.08–
8.14 m (3H, ArH and C4–H), 8.20–8.24 d (1H, Hβ). 13C
NMR spectrum, δC, ppm: 26.0, 51.0, 121.0, 122.3,
122.6, 123.3, 126.5, 127.7, 128.2, 128.5, 130.5, 132.9,
137.1, 137.9, 144.3, 148.4, 156.7, 189.9. Found, %: C
64.87; H 4.70; N 6.88. C22H19BrN2O. Cal-culated, %:
C 64.87, H 4.70; N 6.88. M 407 [M + H]+.
Vf. IR spectrum, ν, cm–1: 1589 (C=C), 1654 (C=O),
2968 (C–H). 1H NMR spectrum, δ, ppm: 1.94–1.97 m
(4H, 2X–CH2–), 3.68–3.72 t (4H, 2XN–CH2–), 7.22–
Vb. IR spectrum, ν, cm–1: 1583 (C=C), 1654
(C=O), 2964(C–H). 1H NMR spectrum, δ, ppm: 1.93–
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1242
D. ASHOK et al.
5. Okten, S., Cakmak, O., Erenler, R., Yuce, O., and
Tekin, S., Turk. J. Chem., 2013, vol. 37, no. 6, p. 896.
6. Meth-Cohn, O., Heterocycles., 1993, vol. 35, p. 539.
7.24 t (1H, C6–H), 7.42–7.46 d (1H, Hα), 7.56–7.67 m
(3H, C7–H, C8–H, and C5–H ), 8.14 s (1H, C4–H),
8.18–8.21 d (2H, ArH), 8.24–8.28 d (1H, Hβ), 8.38–
8.40 d (2H, ArH). 13C NMR spectrum, δC, ppm: 25.5,
50.4, 121.2, 122.8, 124.0, 124.9, 127.2, 127.9, 128.5,
129.0, 131.3, 132.6, 136.5, 141.8, 144.0, 148.5, 151.2,
159.6, 189.2. Found, %: C 70.76; H 5.13; N 11.25.
C22H19N3O3. Calculated, %: C 70.76; H 5.13; N 11.25.
M 374 [M + H]+.
7. Ozdemir, A., Lett. Drug Des. Discov., 2013, vol. 10,
no. 1, p. 44.
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Ger.), 2010, vol. 343, no. 3, p. 173.
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Saritha Jyostna, T., and Achaiah, G., Indian J.
Heterocycl. Chem., 2013, vol. 22, no. 3, p. 229.
Vg. IR spectrum, ν, cm–1: 1592 (C=C), 1666
(C=O), 2965 (C–H). 1H NMR spectrum, δ, ppm: 1.97–
2.00 m (4H, 2X–CH2–), 3.63–3.66 t (4H, 2XN–CH2–),
7.20–7.24 t (1H, C6–H), 7.48–7.58 m (4H, C7–H, C8–H
Hα, and ArH), 7.60–8.00 m (6H, C5–H and ArH ),
8.35–8.40 m (2H, C4–H and Hβ), 8.73–8.76 d (1H,
ArH). 13C NMR spectrum, δC, ppm: 25.8, 50.7, 121.8,
122.8, 123.8, 124.4, 125.9, 127.2, 127.7, 127.9, 128.3,
128.8, 129.5, 130.5, 132.1, 134.9, 135.2, 137.8, 140.2,
145.2, 164.8, 190.0. Found, %: C 82.42; H 5.92; N
7.48. C26H22N2O. Calculated, %: C 82.51; 5.86; N
7.40. M 379 [M + H]+.
10. Arun, Y., Bhaskar, G., Balachandran, C., Ignacimuthu, S.,
and Perumal, P.T., Bioorg. Med. Chem. Lett., 2013,
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Bioorg. Med. Chem. Lett., 2002, vol. 12, p., 1951.
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ACKNOWLEDGMENTS
16. Sreedhar, N.Y., Jayapal, M.R., Sreenivasa Prasad, and
Reddy Prasad, P. Res. J. Pharm. Bio. Chem. Sci., 2010,
vol. 1, no. 4, p. 480.
17. Om Prakash, Ajay Kumar, Anil Sadana, Richa Prakash,
Singh, S.P., Claramunt, R.M., Dionisia Sanz, Ibon
Alkorta, and José Elguero, Tetrahedron., 2005, vol. 61,
p. 6642.
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Kumar, R.P., Bioorg. Med. Chem. Lett., 2005, vol. 15,
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The authors are thankful to the Head of Department
of Chemistry for providing laboratory facilities and to
the Director of Central Facilities for Research and
Development (CFRD), Osmania University for
providing IR and NMR spectral analysis. Financial
support from UGC, New Delhi for AG is gratefully
acknowledged.
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