Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)- pyridinones via azo coupling

Article abstract of DOI:10.1007/s00706-010-0366-5

6-(Substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones were prepared from β-aryl glutaconic acid, which, on fusion with aniline, results in 4-(4-ethoxyphenyl)-1-phenylpyridine-2,6(1H,5H)-dione. This, on further treatment with phosphorus oxych

Full text of DOI:10.1007/s00706-010-0366-5

Monatsh Chem (2010) 141:1123–1133
DOI 10.1007/s00706-010-0366-5
ORIGINAL PAPER
Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-
phenyl-2(1H)-pyridinones via azo coupling
•
N. B. Patel A. I. Gandhi R. D. Sharma
•
Received: 2 August 2009 / Accepted: 1 July 2010 / Published online: 5 August 2010
Ó Springer-Verlag 2010
Abstract 6-(Substituted amino)-4-(4-ethoxyphenyl)-1-phen-
yl-2(1H)-pyridinones were prepared from b-aryl glutaconic
acid, which, on fusion with aniline, results in 4-(4-ethoxy-
phenyl)-1-phenylpyridine-2,6(1H,5H)-dione. This, on further
treatment with phosphorus oxychloride gave 6-chloro-4-(4-
ethoxyphenyl)-1-phenyl-2(1H)-pyridinone, and further treat-
ment with secondary amines yielded 6-(substituted amino)-4-
(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones. These were
subjected to azo coupling with different aryldiazonium chlo-
ridesfurnishingtwoisomers, whichwereseparatedbycolumn
chromatography. All compounds were characterized by ele-
mental analysis, and use of IR and NMR spectral data, and
were evaluated for antimicrobial activity.
motifs have been shown to have significant pharmacolog-
ical properties [4].
Pyridinones have been reported to have non-nucleoside
HIV type I specific reverse transcriptase inhibitor [5] and
anti-inflammatory [6] activity, besides a wide range of
pharmacological activity. They are well known for their
diverse biological activity [7], for example fungicidal,
bactericidal, insecticidal, herbicidal, virucidal, anti-tuber-
cular, and cardiovascular. 2-Pyridinones have also been
reported to be tissue factor VIIa inhibitors [8]. Cyclo-
penta[b]pyridin-2,5-dione is an interesting building block
for access to 2-cyclopenta[b]pyridin-5-ones, seco ana-
logues of 8-azasteroids [9], and it also has antiviral activity
[10, 11].
Keywords 2-Pyridinone ꢀ Secondary amines ꢀ
Aryldiazonium chlorides ꢀ Antimicrobial activity
Orally administrated piperazine is almost devoid of
pharmacological activity. Intravenous administration results
in a transient fall in blood pressure. Lethal doses cause
convulsions and respiratory depression. A large number of
substituted piperazine derivatives have anathematic activity.
Various derivatives of piperazine have actual or potential use
as antihistamines, anaesthetics, analgesics, anticonvulsants,
antispasmodics, and for treatment of hypertension, epilepsy,
burn shock, and haemorrhagic shock. Other, non-medical,
applications of piperazine and its derivatives are as rubber
antioxidants, corrosion inhibitors, wetting and emulsifying
additives, in the cosmetics and dyeing industries, in resins,
polymers, and synthetic fibres, and as analytical reagents
[12–14].
Introduction
2-Pyridinones are an important type of heterocycles with a
variety of biological activity. In particular 2-pyridinones
containing an H-bond acceptor substituent in position 5 are
a relatively new class of specific phosphodiesterase 3
(PDE3) inhibitors [1]. Some of these, e.g. amrinone [2] and
milrinone [3], are good alternatives to classic digitalis
glycosides for acute treatment of congestive heart failure
(CHF). Substituted pyridinones and their dihydro/tetra-
hydro derivatives are found in a wide variety of naturally
occurring alkaloids, and compounds with these structural
Keeping these applications of 2-pyridinones and piper-
azine in mind, and in continuation of our earlier work, we
decided to synthesize 6-amino-substituted 2(1H)-pyridi-
nones from b-aryl glutaconic acid [15]. Substituted
2-pyridinones have been prepared by nucleophilic substi-
tution reactions using heterocyclic groups, for example
methyl/ethyl piperazinyl, etc. under basic conditions. These
N. B. Patel (&) ꢀ A. I. Gandhi ꢀ R. D. Sharma
Department of Chemistry, Veer Narmad South Gujarat
University, Udhna Magdalla Road, Surat 395007, Gujarat, India
e-mail: drnavin@satyam.net.in
123

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N. B. Patel et al.
substituted pyridinones have two nucleophilic positions,
3 and 5 [16–18]. To check the nucleophilicity of these
positions they were subjected for electrophilic substitution
and then characterized by use of spectral data [19, 20]. The
purpose of this work was to observe any variation in
antimicrobial properties after structural changes and SAR
studies.
This experimental testing of antibacterial activity did not
produce results comparable with those from the standard
drug, cefoperazone, even when the substituents at position
C-6 of the pyridinones were changed to methylpiperazine
and ethylpiperazine [14, 22].
Antifungal activity was tested against C. albicans by use
of the diffusion method. This showed that 6-(substituted
amino)-2(1H)-pyridinones with a methylpiperazine and
ethylpiperazine moiety at the C-6 position of the pyridi-
nones were inactive. These derivatives were subjected to
azo coupling and the products obtained were tested for the
antifungal activity in the same way. Mild activity was
observed; ethylpiperazine derivatives had no activity.
Therefore it can be concluded that introduction of a diazo
group to either the C-3 or C-5 position of the pyridinone its
antifungal activity is lost [20, 22, 23].
Result and discussion
Synthesis
Compounds 4 and 5 were subjected to azo coupling. Two
azo-coupled products were obtained, which were separated
by column chromatography on activated silica gel using
ethyl acetate–chloroform (60:40) as mobile phase. The
compounds were characterized as 6-(substituted amino)-3-
(arylazo)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones
6–16 and 30–40 and their 5-(arylazo) isomers 17–27 and
41–51 (Scheme 1, Table 1) on the basis of spectral data.
In the 1H NMR spectrum of 3-(4-chlorophenylazo)-4-(4-
ethoxyphenyl)-6-(4-methylpiperazinyl)-1-phenyl-2(1H)-
pyridinone (9), a proton singlet was observed at 5.9 ppm
because of the proton at the C-5 position, whereas for 5-(4-
chlorophenylazo)-4-(4-ethoxyphenyl)-6-(4-methylpiperazi-
nyl)-1-phenyl-2(1H)-pyridinone (20), a proton singlet was
observed at 6.5 ppm because of the proton at C-3 position.
Experimental
Melting points were determined by means of the open cap-
illary method. IR spectra (KBr pellets) were recorded on a
Perkin–Elmer spectrophotometer. NMR spectra were
recorded in CDCl3 on a Bruker Avance II 400 MHz instru-
ment using TMS as internal standard. Elemental analysis was
performed by means of a Heraeus CHN rapid analyser;
results agreed satisfactorily with calculated values. For TLC
analysis, silica gel coated Al plates (Merck) were used.
6-Chloro-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinone (3)
was synthesized from 1,3-acetonedicarboxylic acid via 1
and 2 according to a procedure published elsewhere [15].
Cl
O
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-1-phenyl-
2(1H)-pyridinone (4, C24H27N3O2)
N
O
N
N
H5C2O
N
A mixture of 3.255 g (0.01 mol) 3 and 2.0 g (0.01 mol)
1-methylpiperazine was heated under reflux for 12 h. The
reaction mass was then poured into acidic crushed ice and
the resulting solid was filtered, washed with water, and
crystallized from acetone to furnish 3.3 g (84.8%) 4. M.p.:
N
N
N
H5C2O
N
N
CH3
N
9
20
CH3
Cl
ꢀ
199–201 °C; IR (KBr): m = 3,020, 2,920 (C–H), 1,700,
1,660 (C=O), 1,245 (C–O–C), 1,430 (C–N) cm-1; 1H NMR
(400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3), 2.5 (s, 3H,
NCH3), 2.7–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H, OCH2),
6.0 (d, 1H, C5–H), 6.6 (d, 1H, C3–H), 7.0–7.7 (m, 9H,
Ar–H) ppm; 13C NMR (100 MHz, CDCl3): d = 14.8, 43.1,
48.9, 55.3, 64.7, 74.9, 114.4, 114.4, 118.9, 120.4, 121.6,
121.6, 124.4, 129.0, 129.0, 129.4, 129.4, 132.8, 138.8,
156.7, 157.5, 160.7 ppm; MS (EI): m/z = 389; HRMS
(EI): m/z calcd [M]? 389.2103, found 389.2101.
After having checked the nucleophilicity at positions 3
and 5, a Mannich reaction was also carried out using sec-
ondary amines, for example 1-methylpiperazine and 1-
ethylpiperazine. The resulting compounds 28, 29, 52, and
53 prove that position 3 is more nucleophilic than position
5 [21].
Antimicrobial activity
Antibacterial activity against two Gram-positive (S. aureus
and B. subtilius) and two Gram-negative (E. coli and
P. vulgarius) bacteria at two concentrations (200 and
400 lg/cm3) was tested by use of the diffusion method.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-1-phenyl-2(1H)-
pyridinone (5, C25H29N3O2)
Compound 5 was prepared similarly to 4 but by reaction of
3 with 1-ethylpiperazine. Yield 3.2 g (79.4%); m.p.:
123

Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones
1125
Scheme 1
COOH
a
O
N
O
H5C2O
H5C2O
COOH
1
2
b
O
N
H5C2O
Cl
3
c
O
N
4: R = -CH3, 5: R = -C2H5
H5C2O
N
4, 5
R'
N
d
d
R
O
N
O
N
e
N
H5C2O
N
N
H5C2O
N
N
R2
N
N
N
R
N
R'
R
N
6-16, 30-40
17-27, 41-51
O
N
H5C2O
N
N
R
28, 29, 52, 53
R = -CH3, -C2H5
R' = H, o-OCH3,o,m,p -Cl,CH3,NO2
a, aniline; b, POCl3; c, methyl- / ethylpiperazine
d, substituted diazonium chlorides; e, Mannich reaction
ꢀ
207–209 °C; IR (KBr): m = 3,020, 2,920 (C–H), 1,700,
1,660 (C=O), 1,245 (C–O–C), 1,430 (C–N) cm-1; 1H NMR
(400 MHz, CDCl3): d = 1.4–1.5 (m, 6H, CH3), 2.5 (q, 2H,
Pip–NCH2), 2.7–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5–H), 6.6 (d, 1H, C3–H), 7.0–7.7 (m,
9H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3): d = 13.4,
14.8, 49.2, 49.2, 49.2, 52.8, 52.8, 64.7, 74.9, 114.4, 114.4,
118.9, 120.4, 121.6, 121.6, 124.4, 129.0, 129.4, 129.4,
132.8, 138.8, 156.7, 157.5, 160.7 ppm; MS (EI):
m/z = 403; HRMS (EI): m/z calcd [M]? 403.2260, found
403.2260.
General procedure for 4-(4-ethoxyphenyl)-6-(4-methyl/
ethylpiperazinyl)-1-phenyl-3/5-(substituted phenylazo)-
2(1H)-pyridinones 6–27 and 30–51
To a precooled (0–5 °C) solution of 4 or 5 (0.01 mol) in
experimental; after 100 cm3 acetone, a precooled (0–5 °C)
solution of benzenediazonium chloride was added (pre-
pared by diazotizing substituted aniline (0.01 mol) in
6 cm3 1:1 HCl with 0.69 g (0.01 mol) NaNO2 in 10 cm3
water). The reaction mixture was poured into 200 cm3
water and then made alkaline by addition of dilute NaOH.
123

1126
N. B. Patel et al.
The coloured product was filtered, washed with water, and
dried. Two azo-coupled products were obtained; these were
separated by column chromatography on activated silica gel
using ethyl acetate–chloroform (60:40) as mobile phase.
Table 1 Characterization data for compounds 6–53
Compound number
R
R2
R0
M.p. (°C) Yield (%)
6
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
H
172–174 36
183–185 35
179–181 36
189–191 35
163–165 34
7
o-Cl
m-Cl
p-Cl
o-CH3
8
General procedure for 4-(4-ethoxyphenyl)-6-(4-methyl/
ethylpiperazinyl)-3-[(4-methyl/ethyl-1-piperazinyl)-
methyl]-1-phenyl-2(1H)-pyridinones 28, 29, 52, 53
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
m-CH3 170–172 35
p-CH3
o-NO2
155–157 35
199–201 35
A mixture of 0.3 g (0.01 mol) paraformaldehyde and 1-
methyl or 1-ethylpiperazine (0.01 mol) was heated under
reflux for 45 min in 50 cm3 chlorobenzene. Compound 4
or 5 (0.01 mol) was then added and the reaction mixture
was heated under reflux for 22 h. The reaction mass was
subjected to steam distillation to remove chlorobenzene.
The solid product was filtered, washed, and recrystallized
from acetone.
m-NO2 186–188 35
p-NO2 179–181 35
o-OCH3 160–162 35
H
148–150 35
161–163 35
182–184 34
168–170 34
150–152 34
o-Cl
m-Cl
p-Cl
o-CH3
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-1-phenyl-3-
(phenylazo)-2(1H)-pyridinone (6, C30H31N5O2)
m-CH3 144–146 35
ꢀ
IR (KBr): m = 1,260 (C–O–C), 1,650 ([C=O), 1,570
(–N=N–), 1,435 (C–N), 3,010, 2,920 (C–H str) cm-1
;
p-CH3
o-NO2
149–151 35
202–204 33
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5–H), 7.0–7.7 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 48.9,
55.3, 55.3, 64.7, 74.9, 114.4, 114.4, 120.4, 121.6, 121.6,
124.0, 124.4, 128.7, 128.8, 128.8, 128.9, 128.8, 128.9,
129.0, 129.0, 129.4, 129.4, 132.8, 146.5, 156.7, 157.5,
158.4 ppm; MS (EI): m/z = 493; HRMS (EI): m/z calcd
[M]? 493.2478, found 493.2475.
m-NO2 207–209 36
p-NO2 189–191 34
o-OCH3 152–154 36
CH3 CH3
CH3 C2H5
C2H5
–
182–184 70
205–207 65
169–171 36
185–187 34
173–175 32
193–195 35
142–144 35
–
H
C2H5
o-Cl
m-Cl
p-Cl
o-CH3
C2H5
C2H5
3-(2-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(7, C30H30ClN5O2)
C2H5
C2H5
m-CH3 159–161 36
C2H5
p-CH3
o-NO2
152–154 36
172–174 36
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,660 ([C=O), 1,575
C2H5
(–N=N–), 1,425 (C–N), 3,020, 2,910 (C–H str) cm-1
;
C2H5
m-NO2 149–151 35
p-NO2 168–170 36
o-OCH3 177–179 36
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.5 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 5.9 (d, 1H, C5–H), 7.0–7.7 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.7, 48.9,
55.4, 55.3, 64.7, 74.9, 114.4, 114.4, 120.3, 121.6, 121.6,
124.0, 124.4, 126.9, 129.0, 129.0, 129.1, 129.4, 129.4,
130.2, 130.2, 132.8, 134.3, 146.5, 156.7, 157.5, 158.4 ppm;
MS (EI): m/z = 527 [M]?, 529 [M ? 2]?; HRMS (EI):
m/z calcd [M]? 527.2088, found 527.2092.
C2H5
C2H5
C2H5
H
170–172 34
175–177 34
188–190 34
179–181 33
152–154 35
C2H5
o-Cl
m-Cl
p-Cl
o-CH3
C2H5
C2H5
C2H5
C2H5
m-CH3 160–162 33
C2H5
p-CH3
o-NO2
146–148 34
166–168 34
3-(3-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(8, C30H30ClN5O2)
C2H5
C2H5
m-NO2 175–177 34
p-NO2 181–183 34
o-OCH3 192–194 35
C2H5
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,670 ([C=O), 1,575
C2H5
(–N=N–), 1,420 (C–N), 3,020, 2,915 (C–H str) cm-1
;
C2H5 CH3
C2H5 C2H5
–
–
182–184 70
195–197 65
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (t, 3H, CH3),
2.4 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 4.1 (q, 2H,
123

Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones
1127
OCH2), 6.0 (d, 1H, C5–H), 7.0–7.7 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 48.9,
55.3, 55.3, 64.7, 74.9, 114.2, 114.4, 120.4, 121.6, 121.6,
124.0, 124.4, 126.9, 128.9, 129.0, 129.0, 129.1, 129.2,
129.4, 130.1, 130.2, 132.8, 134.3, 146.4, 156.7, 157.5,
158.4 ppm; MS (EI): m/z = 527 [M]?, 529 [M ? 2]?;
HRMS (EI): m/z calcd [M]? 527.2088, found 527.2086.
4-(4-Ethoxyphenyl)-3-(4-methylphenylazo)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(12, C31H33N5O2)
IR (KBr): ꢀm = 1,250 (C–O–C), 1,650 ([C=O), 1,560
(–N=N–), 1,425 (C–N), 3,010, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 6H, CH3), 2.6–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 5.9 (d, 1H, C5-H), 7.0–7.7 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 24.3, 43.1, 48.9,
48.9, 55.3, 55.3, 64.7, 74.9, 113.0, 114.3, 114.3, 121.6,
121.6, 124.2, 124.4, 125.7, 127.3, 127.0, 128.7, 128.7,
129.0, 129.1, 129.1, 129.1, 132.8, 138.4, 155.0, 156.7,
156.7, 158.4 ppm; MS (EI): m/z = 507; HRMS (EI):
m/z calcd [M]? 507.2634, found 507.2635.
3-(4-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(9, C30H30ClN5O2)
ꢀ
IR (KBr): m = 1,265 (C–O–C), 1,665 ([C=O), 1,560
(–N=N–), 1,435 (C–N), 3,025, 2,910 (C–H) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.5 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 3.9–4.0 (q,
2H, OCH2), 5.9 (s, 1H, C5–H), 7.0–7.7 (m, 13H, Ar–H)
ppm; 13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9,
48.9, 55.2, 55.3, 64.7, 74.9, 114.4, 114.4, 120.4, 121.6,
121.6, 124.0, 124.4, 126.8, 128.7, 128.9, 129.0, 129.1,
129.4, 129.4, 130.2, 130.2, 132.8, 134.3, 146.5, 156.7,
157.5, 158.4 ppm; MS (EI): m/z = 527 [M]?, 529
[M ? 2]?; HRMS (EI): m/z calcd [M]? 527.2088, found
527.2089.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-3-
(2-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(13, C30H30N6O4)
ꢀ
IR (KBr): m = 1,245 (C–O–C), 1,660 ([C=O), 1,570
(–N=N–), 1,435 (C–N), 3,020, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 3.9–4.0 (q, 2H,
OCH2), 6.0 (d, 1H, C5–H), 7.0–7.7 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 48.9,
55.3, 55.3, 64.7, 74.9, 113.0, 114.3, 114.3, 121.1, 121.6,
121.6, 124.0, 124.2, 127.0, 127.0, 129.0, 129.7, 129.7,
132.8, 134.9, 148.0, 155.0, 156.7, 156.7, 156.7, 158.4 ppm;
MS (EI): m/z = 538; HRMS (EI): m/z calcd [M]?
538.2329, found 538.2326.
4-(4-Ethoxyphenyl)-3-(2-methylphenylazo)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(10, C31H33N5O2)
ꢀ
IR (KBr): m = 1,255 (C–O–C), 1,655 ([C=O), 1,570
(–N=N–), 1,435 (C–N), 3,030, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 6H, CH3), 2.7–3.5 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5–H), 7.0–7.7 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 15.2, 43.1, 48.9,
48.9, 55.3, 55.3, 64.7, 74.9, 114.3, 114.4, 120.4, 121.6,
121.6, 124.0, 124.4, 125.8, 128.1, 128.7, 128.7, 129.0,
129.0, 129.1, 129.4, 129.4, 132.8, 137.1, 146.5, 156.7,
157.5, 158.4 ppm; MS (EI): m/z = 507; HRMS (EI):
m/z calcd [M]? 507.2634, found 507.2629.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-3-
(3-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(14, C30H30N6O4)
ꢀ
IR (KBr): m = 1,260 (C–O–C), 1,655 ([C=O), 1,570
(–N=N–), 1,430 (C–N), 3,020, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (t, 3H, CH3),
2.4 (s, 3H, NCH3), 2.7–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5–H), 7.0–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.7, 48.9,
55.3, 55.3, 64.7, 74.9, 112.9, 114.3, 114.3, 121.1, 121.6,
121.6, 124.0, 124.2, 124.4, 127.0, 127.1, 129.0, 129.0,
129.6, 129.7, 132.8, 134.9, 148.0, 155.0, 156.7, 156.8,
158.4 ppm; MS (EI): m/z = 538; HRMS (EI): m/z calcd
[M]? 538.2329, found 538.2325.
4-(4-Ethoxyphenyl)-3-(3-methylphenylazo)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(11, C31H33N5O2)
ꢀ
IR (KBr): m = 1,240 (C–O–C), 1,660 ([C=O), 1,565
(–N=N–), 1,420 (C–N), 3,025, 2,915 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.3 (s, 6H, CH3), 2.7–3.5 (m, 8H, Pip–H), 3.9–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5–H), 7.0–7.7 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 24.3, 43.1, 48.9,
48.9, 55.3, 55.3, 64.7, 74.9, 114.4, 114.4, 120.4, 121.6,
121.6, 124.0, 124.4, 125.8, 128.6, 128.7, 129.0, 129.0,
129.1, 129.4, 130.4, 132.7, 138.4, 146.5, 156.7 ppm; MS
(EI): m/z = 507; HRMS (EI): m/z calcd [M]? 507.2634,
found 507.2630.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-3-
(4-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(15, C30H30N6O4)
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,650 ([C=O), 1,575
(–N=N–), 1,435 (C–N), 3,010, 2,925 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.5 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5–H), 6.9–7.7 (m, 13H, Ar–H) ppm;
123

1128
N. B. Patel et al.
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 48.9,
55.3, 55.3, 64.7, 74.9, 113.0, 114. 3, 114.3, 121.1, 121.1,
121.6, 121.6, 124.2, 124.4, 126.9, 127.0, 129.0, 129.0,
129.7, 129.7, 132.8, 134.8, 148.0, 155.0, 156.6, 156.7,
158.4 ppm; MS (EI): m/z = 538; HRMS (EI): m/z calcd
[M]? 538.2329, found 538.2334.
5-(3-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(19, C30H30ClN5O2)
IR (KBr): ꢀm = 1,240 (C–O–C), 1,655 ([C=O), 1,560
(–N=N–), 1,425 (C–N), 3,025, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (t, 3H, CH3),
2.4 (s, 3H, NCH3), 2.7–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.2, 48.9, 48.9,
55.3, 55.3, 64.7, 75.0, 114.4, 114.4, 118.9, 120.4, 121.6,
121.6, 124.4, 126.9, 128.9, 129.0, 129.0, 129.1, 129.4,
129.4, 130.1, 130.1, 132.8, 134.3, 146.5, 157.0, 157.5,
160.7 ppm; MS (EI): m/z = 527 [M]?, 529 [M ? 2]?;
HRMS (EI): m/z calcd [M]? 527.2088, found 527.2085.
4-(4-Ethoxyphenyl)-3-(2-methoxyphenylazo)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(16, C31H33N5O3)
ꢀ
IR (KBr): m = 1,255, 1,240 (C–O–C), 1,670 ([C=O),
1,565 (–N=N–), 1,425 (C–N), 3,020, 2,915 (C–H str)
1
cm-1; H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H,
CH3), 2.3 (s, 3H, CH3), 2.6–3.3 (m, 8H, Pip–H), 3.6 (s, 3H,
OCH3), 4.2 (q, 2H, NCH2), 6.0 (s, 1H, C5–H), 7.0–7.8 (m,
13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3): d = 14.8,
43.1, 48.9, 48.9, 55.3, 55.3, 55.9, 64.7, 74.1, 99.6, 113.0,
114.3, 114.3, 114.3, 114.3, 121.1, 121.6, 121.6, 124.2,
124.4, 127.0, 127.0, 129.0, 129.2, 129.7, 129.8, 132.8,
155.0, 156.6, 156.7, 158.4, 159.1 ppm; MS (EI):
m/z = 523; HRMS (EI): m/z calcd [M]? 523.2583, found
523.2576.
5-(4-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(20, C30H30ClN5O2)
ꢀ
IR (KBr): m = 1,245 (C–O–C), 1,660 ([C=O), 1,565
(–N=N–), 1,430 (C–N), 3,020, 2,915 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.5 (s, 3H, NCH3), 2.7–3.4 (m, 8H, Pip–H), 3.9–4.0 (q, 2H,
OCH2), 6.6 (s, 1H, C3–H), 6.9–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 48.9,
55.3, 55.3, 64.6, 75.0, 114.4, 114.4, 118.9, 120.4, 121.6,
121.6, 124.4, 126.8, 128.9, 128.9, 129.0, 129.1, 129.4,
129.4, 130.2, 130.2, 132.8, 134.3, 146.5, 157.1, 157.5,
160.7 ppm; MS (EI): m/z = 527 [M]?, 529 [M ? 2]?;
HRMS (EI): m/z calcd [M]? 527.2088, found 527.2087.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-1-phenyl-5-
(phenylazo)-2(1H)-pyridinone (17, C30H31N5O2)
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,660 ([C=O), 1,565
(–N=N–), 1,430 (C–N), 3,020, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.5 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.7 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 49.0,
55.3, 55.3, 64.7, 75.0, 114.4, 114.4, 118.9, 120.4, 121.6,
121.6, 124.4, 128.7, 128.8, 128.8, 128.8, 128.9, 128.9,
129.0, 129.0, 129.4, 129.4, 132.8, 146.5, 157.0, 157.5,
160.7 ppm; MS (EI): m/z = 493; HRMS (EI): m/z calcd
[M]? 493.2478, found 493.2479.
4-(4-Ethoxyphenyl)-5-(2-methylphenylazo)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(21, C31H33N5O2)
ꢀ
IR (KBr): m = 1,245 (C–O–C), 1,650 ([C=O), 1,575
(–N=N–), 1,445 (C–N), 3,020, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.5 (s, 6H, CH3), 2.7–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 6.9–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 15.2, 43.1, 48.9,
48.9, 55.3, 55.3, 64.7, 75.0, 114.4, 114.4, 118.9, 120.4,
121.6, 121.6, 124.4, 125.8, 128.1, 128.7, 128.7, 129.0,
129.0, 129.1, 129.4, 129.4, 132.8, 137.1, 146.5, 157.0,
157.5, 160.7 ppm; MS (EI): m/z = 507; HRMS (EI): m/z calcd
[M]? 507.2634, found 507.2631.
5-(2-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(18, C30H30ClN5O2)
ꢀ
IR (KBr): m = 1,255 (C–O–C), 1,650 ([C=O), 1,570
(–N=N–), 1,420 (C–N), 3,025, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 3.9–4.0 (q,
2H, OCH2), 6.5 (d, 1H, C3–H), 7.0–7.7 (m, 13H, Ar–H)
ppm; 13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9,
48.9, 55.2, 55.3, 64.7, 75.0, 114.3, 114.4, 118.9, 120.4,
121.6, 121.6, 124.4, 126.9, 128.9, 129.0, 129.0, 129.1,
129.4, 129.4, 130.2, 130.2, 132.8, 134.3, 146.5, 157.1,
157.5, 160.7 ppm; MS (EI): m/z = 527 [M]?, 529
[M ? 2]?; HRMS (EI): m/z calcd [M]? 527.2088, found
527.2083.
4-(4-Ethoxyphenyl)-5-(3-methylphenylazo)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(22, C31H33N5O2)
ꢀ
IR (KBr): m = 1,265 (C–O–C), 1,665 ([C=O), 1,570
(–N=N–), 1,430 (C–N), 3,020, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 6H, CH3), 2.7–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
123

Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones
1129
OCH2), 6.5 (d, 1H, C3–H), 7.0–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 24.3, 43.1, 48.9,
48.8, 55.3, 55.3, 64.7, 75.0, 114.3, 114.4, 118.9, 120.4,
121.6, 121.6, 124.4, 125.8, 128.6, 128.7, 129.0, 129.1,
129.1, 129.4, 129.4, 130.4, 132.8, 138.4, 146.4, 157.0,
157.5, 160.7 ppm; MS (EI): m/z = 507; HRMS (EI): m/z
calcd [M]? 507.2634, found 507.2634.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-5-
(4-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(26, C30H30N6O4)
IR (KBr): ꢀm = 1,255 (C–O–C), 1,655 ([C=O), 1,570
(–N=N–), 1,430 (C–N), 3,020, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (t, 3H, CH3),
2.5 (s, 3H, NCH3), 2.6–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.5 (d, 1H, C3–H), 7.0–7.7 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 48.9,
55.1, 55.3, 64.7, 75.0, 114.4, 114.5, 118.9, 120.4, 121.1,
121.1, 121.6, 121.6, 124.4, 129.0, 129.0, 129.4, 129.4,
129.7, 129.8, 132.8, 134.8, 146.5, 147.8, 157.0, 157.5 ppm;
MS (EI): m/z = 538; HRMS (EI): m/z calcd [M]?
538.2329, found 538.2330.
4-(4-Ethoxyphenyl)-5-(4-methylphenylazo)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(23, C31H33N5O2)
ꢀ
IR (KBr): m = 1,255 (C–O–C), 1,660 ([C=O), 1,565
(–N=N–), 1,435 (C–N), 3,020, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.5 (s, 6H, CH3), 2.7–3.4 (m, 8H, Pip–H), 3.9–4.1 (q,
2H, OCH2), 6.6 (d, 1H, C3–H), 6.9–7.5 (m, 13H, Ar–H)
ppm; 13C NMR (100 MHz, CDCl3): d = 14.8, 24.3,
43.1, 48.9, 48.9, 55.3, 55.3, 64.7, 75.0, 114.4, 114.4,
118.9, 120.4, 121.6, 121.6, 124.4, 125.7, 128.7, 128.7,
128.8, 129.0, 129.1, 129.1, 129.4, 129.4, 132.8, 138.4,
146.6, 157.0, 157.5, 160.7 ppm; MS (EI): m/z =
507; HRMS (EI): m/z calcd [M]? 507.2634, found
507.2629.
4-(4-Ethoxyphenyl)-5-(2-methoxyphenylazo)-6-
(4-methylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(27, C31H33N5O3)
ꢀ
IR (KBr): m = 1,260, 1,250 (C–O–C), 1,660 ([C=O),
1,570 (–N=N–), 1,420 (C–N), 3,015, 2,910 (C–H str)
1
cm-1; H NMR (400 MHz, CDCl3): d = 1.3–1.5 (t, 3H,
CH3), 2.4 (s, 3H, CH3), 2.6–3.5 (m, 8H, Pip–H), 3.6 (s, 3H,
OCH3), 4.2 (q, 2H, NCH2), 6.6 (s, 1H, C3–H), 7.0–7.8 (m,
13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3): d = 14.8,
43.1, 48.8, 48.9, 55.3, 55.3, 55.9, 64.7, 75.0, 99.6, 114.3,
114.4, 114.4, 118.9, 120.4, 121.1, 121.6, 121.7, 124.4,
129.0, 129.1, 129.4, 129.4, 129.8, 129.8, 132.8, 146.5,
157.0, 157.5, 159.1, 160.7 ppm; MS (EI): m/z = 523;
HRMS (EI): m/z calcd [M]? 523.2583, found 523.2577.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-5-
(2-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(24, C30H30N6O4)
ꢀ
IR (KBr): m = 1,240 (C–O–C), 1,665 ([C=O), 1,575
(–N=N–), 1,430 (C–N), 3,015, 2,915 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 3H, NCH3), 2.8–3.6 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 6.9–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 48.9,
55.2, 55.3, 64.7, 75.0, 114.4, 114.4, 118.9, 120.4, 121.1,
121.6, 121.6, 124.0, 124.4, 129.0, 129.0, 129.4, 129.4,
129.7, 129.7, 132.8, 134.9, 146.5, 147.9, 157.0, 157.5,
160.7 ppm; MS (EI): m/z = 538; HRMS (EI): m/z calcd
[M]? 538.2329, found 538.2335.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-3-[(4-methyl-
piperazinyl)methyl]-1-phenyl-2(1H)-pyridinone
(28, C30H39N5O2)
ꢀ
IR (KBr): m = 1,260 (C–O–C), 1,650 ([C=O), 1,570
(–N=N–), 1,435 (C–N), 3,010, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4 (t, 3H, CH3), 2.4
(s, 4H, NCH3), 2.6 (s, 2H, CH2), 2.3 (q, 2H, NCH2),
2.7–3.4 (m, 16H, Pip–H), 3.5 (s, 2H, OCH2), 5.9 (d, 1H,
C5–H), 6.7–7.6 (m, 9H, Ar–H) ppm; 13C NMR (100 MHz,
CDCl3): d = 14.8, 43.1, 43.1, 48.9, 48.9, 52.4, 52.4, 55.2,
55.3, 55.3, 55.3, 57.9, 64.7, 74.9, 114.4, 114.4, 120.4,
121.6, 121.6, 124.4, 129.0, 129.0, 129.4, 129.4, 132.8,
134.8, 135.3, 156.7, 157.5, 158.3 ppm; MS (EI):
m/z = 501; HRMS (EI): m/z calcd [M]? 501.3104, found
501.3105.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-5-
(3-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(25, C30H30N6O4)
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,650 ([C=O), 1,560
(–N=N–), 1,425 (C–N), 3,010, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 3H, NCH3), 2.7–3.5 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.7 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 14.8, 43.1, 48.9, 48.9,
55.3, 55.3, 64.7, 75.0, 114.4, 114.4, 118.9, 120.4, 121.1,
121.6, 121.6, 124.0, 124.4, 129.0, 129.1, 129.4, 129.4,
129.6, 129.7, 132.8, 134.9, 146.5, 148.0, 157.0, 157.5,
160.7 ppm; MS (EI): m/z = 538; HRMS (EI): m/z calcd
[M]? 538.2329, found 538.2327.
4-(4-Ethoxyphenyl)-6-(4-methylpiperazinyl)-3-[(4-ethyl-
piperazinyl)methyl]-1-phenyl-2(1H)-pyridinone
(29, C31H41N5O2)
ꢀ
IR (KBr): m = 1,260 (C–O–C), 1,650 ([C=O), 1,570
(–N=N–), 1,435 (C–N), 3,010, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.5 (t, 3H, CH3), 2.3 (s,
2H, NCH3), 2.4 (s, 2H, NCH3), 2.6 (s, 4H, CH2), 2.3 (q,
123

1130
N. B. Patel et al.
2H, NCH2), 2.7–3.3 (m, 16H, Pip–H), 3.5 (s, 2H, OCH2),
6.0 (d, 1H, C5-H), 6.7–7.6 (m, 9H, Ar–H) ppm; 13C NMR
(100 MHz, CDCl3): d = 13.4, 14.8, 43.1, 48.9, 48.9, 49.2,
52.7, 57.8, 52.8, 52.8, 55.3, 55.3, 57.9, 64.7, 74.9, 114.4,
114.5, 120.4, 121.6, 121.6, 124.4, 129.0, 129.0, 129.4,
129.5, 132.8, 134.8, 135.3, 156.8, 157.5, 158.3 ppm; MS
(EI): m/z = 515; HRMS (EI): m/z calcd [M]? 515.3260,
found 515.3257.
3-(4-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-ethylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(33, C31H32ClN5O2)
IR (KBr): ꢀm = 1,260 (C–O–C), 1,660 ([C=O), 1,565
(–N=N–), 1,430 (C–N), 3,025, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.31.5 (m, 6H, CH3),
2.4 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.1 (d, 1H, C5-H), 7.0–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 29.4, 49.1,
49.2, 49.2, 52.8, 52.8, 64.7, 74.9, 114.4, 114.4, 120.4,
121.6, 121.6, 124.0, 124.4, 126.8, 128.9, 128.9, 129.0,
129.0, 129.4, 130.2, 130.2, 132.8, 134.3, 146.5, 156.7,
157.5, 158.6 ppm; MS (EI): m/z = 541 [M]?, 543
[M ? 2]?; HRMS (EI): m/z calcd [M]? 541.2245, found
541.2247.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-1-phenyl-3-
(phenylazo)-2(1H)-pyridinone (30, C31H33N5O2)
ꢀ
IR (KBr): m = 1,255 (C–O–C), 1,665 ([C=O), 1,575
(–N=N–), 1,425 (C–N), 3,020, 2,915 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.6 (q, 2H, NCH2), 2.7–3.4 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5-H), 7.0–7.6 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.1, 49.2,
49.2, 52.8, 52.8, 64.7, 74.9, 114.4, 114.4, 120.4, 121.6,
121.6, 124.1, 124.4, 128.7, 128.8, 128.8, 128.8, 128.9,
128.9, 129.0, 129.0, 129.4, 129.4, 132.8, 146.5, 156.7,
157.5, 158.4 ppm; MS (EI): m/z = 507; HRMS (EI):
m/z calcd [M]? 507.2634, found 507.2631.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-
(2-methylphenylazo)-1-phenyl-2(1H)-pyridinone
(34, C32H35N5O2)
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,650 ([C=O), 1,575
(–N=N–), 1,445 (C–N), 3,025, 2,905 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 6H, CH3), 2.5 (q, 2H, NCH2), 2.7–3.5 (m, 8H,
Pip–H), 4.0–4.1 (q, 2H, OCH2), 6.0 (d, 1H, C5-H), 7.0–7.7
(m, 13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3):
d = 13.4, 14.8, 15.2, 49.2, 49.2, 49.2, 52.8, 52.9, 64.7,
74.9, 114.4, 114.4, 120.4, 121.6, 121.6, 124.1, 124.4,
125.8, 128.1, 128.7, 128.8, 129.0, 129.1, 129.1, 129.4,
129.4, 132.8, 137.1, 146.5, 156.7, 157.5, 158.4 ppm; MS
(EI): m/z = 521; HRMS (EI): m/z calcd [M]? 521.2791,
found 521.2786.
3-(2-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-ethylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(31, C31H32ClN5O2)
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,655 ([C=O), 1,570
(–N=N–), 1,420 (C–N), 3,010, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.1 (d, 1H, C5-H), 7.0–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.9, 49.2, 49.2,
49.2, 52.8, 52.6, 64.7, 74.9, 114.3, 114.4, 120.4, 121.5,
121.6, 124.0, 124.4, 126.9, 128.9, 129.0, 129.0, 129.1,
129.4, 129.4, 130.2, 130.2, 132.8, 134.3, 146.5, 156.7,
157.5, 158.5 ppm; MS (EI): m/z = 541 [M]?, 543
[M ? 2]?; HRMS (EI): m/z calcd [M]? 541.2245, found
541.2245.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-
(3-methylphenylazo)-1-phenyl-2(1H)-pyridinone
(35, C32H35N5O2)
ꢀ
IR (KBr): m = 1,245 (C–O–C), 1,655 ([C=O), 1,570
(–N=N–), 1,430 (C–N), 3,020, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.6 (t, 3H, CH3),
2.3 (s, 6H, CH3), 2.5 (q, 2H, NCH2), 2.7–3.5 (m, 8H,
Pip–H), 4.0–4.1 (q, 2H, OCH2), 5.9 (d, 1H, C5-H), 7.0–7.7
(m, 13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3):
d = 13.4, 41.7, 24.3, 49.2, 49.2, 49.2, 52.8, 52.8, 64.7,
74.9, 114.4, 114.5, 120.4, 121.6, 121.7, 124.0, 124.4, 125.8,
128.6, 128.8, 129.0, 129.0, 129.1, 129.4, 130.4, 132.8, 138.4,
146.5, 156.7, 157.5, 158.5 ppm; MS (EI): m/z = 521; HRMS
(EI): m/z calcd [M]? 521.2791, found 521.2793.
3-(3-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-ethylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(32, C31H32ClN5O2)
ꢀ
IR (KBr): m = 1,260 (C–O–C), 1,660 ([C=O), 1,570
(–N=N–), 1,425 (C–N), 3,020, 2,915 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.5 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.6–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5-H), 7.0–7.7 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.1, 49.2,
49.2, 52.8, 52.8, 64.7, 74.9, 114.4, 114.4, 120.4, 121.6,
121.6, 124.1, 124.4, 126.9, 128.9, 129.0, 129.0, 129.1,
129.4, 129.4, 130.1, 130.2, 132.8, 134.3, 146.4, 156.8,
157.5, 158.4 ppm; MS (EI): m/z = 541 [M]?, 543
[M ? 2]?; HRMS (EI): m/z calcd [M]? 541.2245, found
541.2243.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-
(4-methylphenylazo)-1-phenyl-2(1H)-pyridinone
(36, C32H35N5O2)
ꢀ
IR (KBr): m = 1,260 (C–O–C), 1,650 ([C=O), 1,565
(–N=N–), 1,435 (C–N), 3,015, 2,905 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.6 (t, 3H, CH3),
2.4 (s, 6H, CH3), 2.5 (q, 2H, NCH2), 2.7–3.5 (m, 8H,
123

Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones
1131
Pip–H), 4.0–4.1 (q, 2H, OCH2), 6.0 (d, 1H, C5-H), 7.0–7.6
(m, 13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3):
d = 13.4, 14.8, 24.3, 49.2, 49.2, 49.2, 52.8, 52.8, 64.5,
74.9, 114.4, 114.4, 120.4, 121.6, 121.6, 124.0, 124.4,
125.7, 128.7, 128.7, 129.0, 129.0, 129.1, 129.1, 129.4,
129.4, 132.8, 138.2, 146.5, 156.7, 157.5, 158.4 ppm; MS
(EI): m/z = 521; HRMS (EI): m/z calcd [M]? 521.2791,
found 521.2790.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-
(2-methoxyphenylazo)-1-phenyl-2(1H)-pyridinone
(40, C32H35N5O3)
IR (KBr): ꢀm = 1,250, 1,245 (C–O–C), 1,660 ([C=O),
1,575 (–N=N–), 1,435 (C–N), 3,020, 2,915 (C–H str)
1
cm-1; H NMR (400 MHz, CDCl3): d = 1.3–1.5 (t, 3H,
CH3), 2.4 (s, 6H, CH3), 2.6–3.5 (m, 8H, Pip–H), 3.6 (s, 3H,
OCH3), 4.2 (q, 2H, NCH2), 6.0 (s, 1H, C5-H), 7.0–7.8 (m,
13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3): d = 13.4,
14.8, 49.2, 49.2, 49.3, 52.8, 52.8, 55.9, 64.7, 74.7, 99.6,
114.3, 114.4, 114.4, 120.4, 121.1, 121.6, 121.6, 124.0,
124.4, 129.0, 129.1, 129.4, 129.8, 129.9, 132.8, 146.5,
156.7, 157.5, 158.4, 159.1 ppm; MS (EI): m/z = 537;
HRMS (EI): m/z calcd [M]? 537.2740, found 537.2738.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-
(2-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(37, C31H32N6O4)
ꢀ
IR (KBr): m = 1,265 (C–O–C), 1,660 ([C=O), 1,575
(–N=N–), 1,430 (C–N), 3,025, 2,905 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.5 (m, 6H,
CH3), 2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H),
4.0–4.2 (q, 2H, OCH2), 6.0 (d, 1H, C5-H), 7.0–7.6 (m,
13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3):
d = 13.4, 14.8, 49.2, 49.2, 49.2, 52.8, 52.9, 64.7, 74.9,
114.4, 114.4, 120.5, 121.1, 121.4, 121.6, 124.0, 124.0,
124.4, 129.0, 129.0, 129.4, 129.4, 129.7, 129.7, 132.8,
134.9, 146.5, 148.1, 156.7, 157.5, 158.4 ppm; MS (EI):
m/z = 552; HRMS (EI): m/z calcd [M]? 552.2485,
found 552.2481.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-1-
phenyl-5-(phenylazo)-2(1H)-pyridinone
(41, C31H33N5O2)
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,660 ([C=O), 1,570
(–N=N–), 1,430 (C–N), 3,025, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.6 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 14.8, 49.2,
49.2, 49.3, 52.8, 52.8, 64.7, 75.0, 114.4, 114.4, 118.9,
120.4, 121.6, 121.6, 124.4, 128.7, 128.8, 128.8, 128.9,
129.0, 129.1, 129.4, 132.8, 146.5, 157.0, 157.5, 160.7 ppm;
MS (EI): m/z = 507; HRMS (EI): m/z calcd [M]?
507.2634, found 507.2637.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-
(3-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(38, C31H32N6O4)
ꢀ
IR (KBr): m = 1,255 (C–O–C), 1,650 ([C=O), 1,570
(–N=N–), 1,430 (C–N), 3,025, 2,915 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.6 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 5.9 (d, 1H, C5-H), 7.0–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.2, 49.2,
49.3, 52.8, 52.8, 64.7, 74.9, 114.2, 114.4, 120.4, 121.1,
121.6, 121.6, 124.0, 124.0, 124.4, 129.0, 129.1, 129.4,
129.4, 129.6, 129.7, 132.8, 134.9, 146.5, 148.0, 156.7,
157.5, 158.3 ppm; MS (EI): m/z = 552; HRMS (EI): m/z
calcd [M]? 552.2485, found 552.2487.
5-(2-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-ethylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(42, C31H32ClN5O2)
ꢀ
IR (KBr): m = 1,255 (C–O–C), 1,670 ([C=O), 1,575
(–N=N–), 1,425 (C–N), 3,020, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.6 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.9, 49.2, 49.2,
49.2, 52.8, 52.6, 64.7, 75.0, 114.4, 114.4, 118.9, 120.4,
121.6, 124.4, 126.9, 128.9, 129.0, 129.0, 129.1, 129.4,
129.4, 130.2, 130.2, 132.8, 134.3, 146.5, 157.1, 157.5,
160.7 ppm; MS (EI): m/z = 541 [M]?, 543 [M ? 2]?;
HRMS (EI): m/z calcd [M]? 541.2245, found 541.2241.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-
(4-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(39, C31H32N6O4)
ꢀ
IR (KBr): m = 1,255 (C–O–C), 1,655 ([C=O), 1,570
(–N=N–), 1,430 (C–N), 3,020, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.0 (d, 1H, C5-H), 7.0–7.6 (m, 13H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.2, 49.2,
49.2, 52.8, 52.8, 64.7, 74.9, 114.4, 114.4, 120.4, 121.1,
121.2, 121.6, 121.6, 124.0, 124.4, 129.0, 129.0, 129.4,
129.4, 129.7, 129.7, 132.8, 134.8, 146.5, 148.1, 156.7,
157.5, 158.4 ppm; MS (EI): m/z = 552; HRMS (EI): m/z
calcd [M]? 552.2485, found 552.2481.
5-(3-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-ethylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(43, C31H32ClN5O2)
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,660 ([C=O), 1,575
(–N=N–), 1,430 (C–N), 3,010, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.6 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.1, 49.2,
123

1132
N. B. Patel et al.
49.2, 52.8, 52.8, 64.7, 75.0, 114.4, 114.3, 118.9, 120.4,
121.6, 121.6, 124.4, 126.9, 128.9, 129.0, 129.0, 129.1,
129.4, 129.4, 130.1, 130.2, 132.8, 134.3, 146.5, 157.0,
157.5, 160.7 ppm; MS (EI): m/z = 541 [M]?, 543
[M ? 2]?; HRMS (EI): m/z calcd [M]? 541.2245, found
541.2246.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-5-
(4-methylphenylazo)-1-phenyl-2(1H)-pyridinone
(47, C32H35N5O2)
IR (KBr): ꢀm = 1,265 (C–O–C), 1,650 ([C=O), 1,560
(–N=N–), 1,420 (C–N), 3,015, 2,900 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.6 (t, 3H, CH3),
2.3 (s, 6H, CH3), 2.5 (q, 2H, NCH2), 2.7–3.4 (m, 8H,
Pip–H), 4.0–4.1 (q, 2H, OCH2), 6.5 (d, 1H, C3–H), 6.9–7.6
(m, 13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3):
d = 13.4, 14.8, 24.3, 49.1, 49.2, 49.2, 52.8, 52.8, 64.7,
75.0, 114.4, 114.2, 118.9, 120.4, 121.3, 121.6, 124.4,
125.7, 128.7, 128.7, 129.0, 129.0, 129.1, 129.1, 129.4,
129.4, 132.8, 138.4, 146.5, 157.0, 157.5, 160.7 ppm; MS
(EI): m/z = 521; HRMS (EI): m/z calcd [M]? 521.2791,
found 521.2793.
5-(4-Chlorophenylazo)-4-(4-ethoxyphenyl)-6-
(4-ethylpiperazinyl)-1-phenyl-2(1H)-pyridinone
(44, C31H32ClN5O2)
ꢀ
IR (KBr): m = 1,255 (C–O–C), 1,665 ([C=O), 1,570
(–N=N–), 1,435 (C–N), 3,030, 2,905 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.6 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.2, 49.2,
49.2, 52.6, 52.7, 64.7, 75.0, 114.4, 114.4, 118.9, 120.4,
121.6, 121.6, 124.5, 126.8, 128.9, 128.9, 129.0, 129.1,
129.4, 129.4, 130.2, 130.2, 132.7, 134.3, 146.5, 157.0,
157.5, 160.7 ppm; MS (EI): m/z = 541 [M]?, 543
[M ? 2]?; HRMS (EI): m/z calcd [M]? 541.2245, found
541.2245.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-5-
(2-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(48, C31H32N6O4)
ꢀ
IR (KBr): m = 1,260 (C–O–C), 1,665 ([C=O), 1,570
(–N=N–), 1,435 (C–N), 3,030, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.6 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.2, 49.2,
49.2, 52.8, 52.8, 64.7, 75.1, 114.4, 114.4, 118.9, 120.4,
121.1, 121.6, 121.6, 124.0, 124.4, 129.0, 129.0, 129.4,
129.4, 129.7, 129.7, 132.8, 134.9, 146.5, 148.0, 157.0,
157.5, 160.0 ppm; MS (EI): m/z = 552; HRMS (EI):
m/z calcd [M]? 552.2485, found 552.2481.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-5-
(2-methylphenylazo)-1-phenyl-2(1H)-pyridinone
(45, C32H35N5O2)
ꢀ
IR (KBr): m = 1,240 (C–O–C), 1,640 ([C=O), 1,570
(–N=N–), 1,420 (C–N), 3,010, 2,915 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.6 (t, 3H, CH3),
2.3 (s, 6H, CH3), 2.5 (q, 2H, NCH2), 2.7–3.5 (m, 8H,
Pip–H), 4.0–4.1 (q, 2H, OCH2), 6.6 (d, 1H, C3–H), 7.0–7.7
(m, 13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3):
d = 13.4, 14.8, 15.2, 49.1, 49.2, 49.2, 52.8, 52.8, 64.7,
75.0, 114.4, 114.4, 118.9, 120.4, 121.6, 121.6, 124.4,
125.8, 128.1, 128.7, 128.7, 129.0, 129.0, 129.1, 129.4,
129.4, 132.8, 137.1, 146.5, 157.0, 157.5, 160.7 ppm; MS
(EI): m/z = 521; HRMS (EI): m/z calcd [M]? 521.2791,
found 521.2787.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-5-
(3-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(49, C31H32N6O4)
ꢀ
IR (KBr): m = 1,250 (C–O–C), 1,645 ([C=O), 1,575
(–N=N–), 1,420 (C–N), 3,025, 2,910 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.6 (m, 14H, Ar–H) ppm;
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.2, 49.2,
49.2, 52.8, 52.8, 64.7, 75.1, 114.3, 114.4, 118.9, 120.4,
121.1, 121.6, 121.6, 123.4, 124.4, 129.0, 128.7, 129.4,
129.4, 129.6, 129.7, 132.6, 134.9, 146.5, 148.0, 157.0,
157.5, 160.7 ppm; MS (EI): m/z = 552; HRMS (EI): m/z
calcd [M]? 552.2485, found 552.2479.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-5-
(3-methylphenylazo)-1-phenyl-2(1H)-pyridinone
(46, C32H35N5O2)
ꢀ
IR (KBr): m = 1,240 (C–O–C), 1,645 ([C=O), 1,575
(–N=N–), 1,425 (C–N), 3,010, 2,905 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.4–1.5 (t, 3H, CH3),
2.4 (s, 6H, CH3), 2.5 (q, 2H, NCH2), 2.7–3.6 (m, 8H,
Pip–H), 4.0–4.1 (q, 2H, OCH2), 6.6 (d, 1H, C3–H), 7.0–7.7
(m, 13H, Ar–H) ppm; 13C NMR (100 MHz, CDCl3):
d = 13.4, 14.8, 24.3, 49.2, 49.2, 49.3, 52.8, 52.9, 64.7,
75.0, 114.4, 114.5, 118.9, 120.4, 121.4, 121.6, 124.4,
125.8, 128.6, 128.7, 129.0, 129.0, 129.1, 129.4, 129.4,
130.4, 132.8, 138.4, 146.5, 157.1, 157.5, 160.7 ppm; MS
(EI): m/z = 521; HRMS (EI): m/z calcd [M]? 521.2791,
found 521.2793.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-5-
(4-nitrophenylazo)-1-phenyl-2(1H)-pyridinone
(50, C31H32N6O4)
ꢀ
IR (KBr): m = 1,240 (C–O–C), 1,650 ([C=O), 1,575
(–N=N–), 1,425 (C–N), 3,030, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.4 (m, 6H, CH3),
2.5 (q, 2H, NCH2), 2.7–3.3 (m, 8H, Pip–H), 4.0–4.1 (q, 2H,
OCH2), 6.6 (d, 1H, C3–H), 7.0–7.6 (m, 14H, Ar–H) ppm;
123

Synthesis of novel 6-(substituted amino)-4-(4-ethoxyphenyl)-1-phenyl-2(1H)-pyridinones
1133
13C NMR (100 MHz, CDCl3): d = 13.4, 14.8, 49.2, 49.2,
49.2, 52.8, 52.8, 64.7, 74.8, 114.4, 114.4, 118.9, 120.4,
121.1, 121.1, 121.6, 121.6, 124.4, 129.0, 129.0, 129.4,
129.4, 129.7, 129.7, 132.8, 134.8, 146.3, 148.0, 156.7,
157.5, 160.5 ppm; MS (EI): m/z = 552; HRMS (EI): m/z calcd
[M]? 552.2485, found 552.2483.
156.7, 157.5, 158.3 ppm; MS (EI): m/z = 529; HRMS
(EI): m/z calcd [M]? 529.3417, found 529.3411.
Acknowledgments The authors are grateful to the Head of the
Chemistry Department, Veer Narmad South Gujarat University,
Surat, Gujarat, for providing laboratory facilities, and to the SAIF,
Punjab University, Chandigarh, for NMR spectra.
4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-5-
(2-methoxyphenylazo)-1-phenyl-2(1H)-pyridinone
(51, C32H35N5O3)
References
ꢀ
IR (KBr): m = 1,260 (C–O–C), 1,650 ([C=O), 1,570
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(–N=N–), 1,435 (C–N), 3,010, 2,920 (C–H str) cm-1
;
1H NMR (400 MHz, CDCl3): d = 1.3–1.5 (t, 3H, CH3),
2.4 (s, 6H, CH3), 2.6–3.5 (m, 8H, Pip–H), 3.6 (s, 3H,
OCH3), 4.2 (q, 2H, NCH2), 6.6 (s, 1H, C3–H), 7.0–7.8 (m,
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4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-[(4-methyl-
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(52, C31H41N5O2)
ꢀ
IR (KBr): m = 3,035, 2,925 (C–H), 1,660 ([C=O), 1,245
(C–O–C), 1,430 (C = N) cm-1 1H NMR (400 MHz,
;
CDCl3): d = 1.4–1.5 (t, 3H, CH3), 2.3 (q, 6H, CH3), 2.4
(s, 2H, NCH2), 2.6 (s, 4H, CH2), 2.7–3.4 (m, 16H, Pip–H),
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43.1, 49.2, 49.2, 49.3, 52.4, 52.4, 52.8, 52.8, 55.3, 55.3,
57.9, 64.7, 74.9, 114.4, 114.4, 120.4, 121.6, 121.6, 124.4,
129.0, 129.0, 129.4, 129.4, 132.8, 134.8, 135.5, 156.7,
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4-(4-Ethoxyphenyl)-6-(4-ethylpiperazinyl)-3-[(4-ethyl-
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(53, C32H43N5O2)
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123