Synthesis and antimicrobial of some novel-5-carbomethoxy-2-pyridone derivatives containing sulfonamide moiety

Article abstract of DOI:10.1080/10426500802067789

Dimethyl 4-(methoxymethylene)-2-pentenedioate 2 was selected as the starting material for the synthesis of some novel 2-pyridones containing sulfonamide moiety, which we expected to have biological activities such as bactericidal and fungicidal or other a

Full text of DOI:10.1080/10426500802067789

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Synthesis and Antimicrobial of
Some Novel-5-carbomethoxy-2-
pyridone Derivatives
Containing Sulfonamide Moiety
Fatma El-Mariah a & Ekhlass Nassar a
a Department of Chemistry, Faculty of Girls , Ain
Shams University , Cairo, Egypt
Published online: 03 Nov 2008.
To cite this article: Fatma El-Mariah & Ekhlass Nassar (2008) Synthesis and
Antimicrobial of Some Novel-5-carbomethoxy-2-pyridone Derivatives Containing
Sulfonamide Moiety, Phosphorus, Sulfur, and Silicon and the Related Elements, 183:12,
3145-3155, DOI: 10.1080/10426500802067789
To link to this article: http://dx.doi.org/10.1080/10426500802067789
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Phosphorus, Sulfur, and Silicon, 183:3145–3155, 2008
Copyright © Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426500802067789
Synthesis and Antimicrobial of Some Novel-
5-carbomethoxy-2-pyridone Derivatives Containing
Sulfonamide Moiety
Fatma El-Mariah and Ekhlass Nassar
Department of Chemistry, Faculty of Girls, Ain Shams University,
Cairo, Egypt
Dimethyl 4-(methoxymethylene)-2-pentenedioate 2 was selected as the starting ma-
terial for the synthesis of some novel 2 - pyridones containing sulfonamide moiety,
which we expected to have biological activities such as bactericidal and fungicidal
or other applications of certain interest.
Keywords Antimicrobial activity; coumalic acid; p-substituted aniline; n-substituted
5-carbomethoxy-2-pyridones
INTRODUCTION
A number of biologically active compounds possessing 2-pyridone moi-
ety have been known.1−3 On the other hand, 5-carboxy-2-pyridone has
been used as a key intermediate for the synthesis of recently de-
veloped insecticide. There have been several reports for the synthe-
sis of carboalkoxy-2-pyridones from alkylcoumalate.4 However, prepa-
rations of alkylcoumalate from coumalic acid 1 have some prob-
lems such as low yield or use of expensive coupling agents.5 Also,
the yields for the synthesis of N-aryl-5-carboalkoxy-2-pyridones, from
alkylcoumalate were poor.4a Other synthetic methods for carboalkoxy-
2-pyridones consist of cyclization of dienamino esters prepared from
enamino ester6a or cyclic sulfonamide.6b We have been interested in
the synthesis of some heterocycles containing sulfonamide moiety.7
This is because they have been found to possess a wide range of
Received 5 January 2008; accepted 25 March 2008.
The author acknowledges the help of Dr. Gamal El-Sherbeney, Department of Mi-
crobiology, Faculty of Science, El-Azhar University, Cairo, Egypt, for carrying out the
antimicrobial activity.
Address correspondence to Ekhlass Nassar, Department of Chemistry, Faculty of
Girls, Ain Shams University, Cairo. E-mail: ekhlass nassar@hotmail.com
3145

3146
F. El-Mariah and E. Nassar
biological activities8such as anticonvulsant, hypoglycemic, antihyper-
tensive, histamine-H2-receptor antagonistic, and herbicidal activities.3
RESULTS AND DISCUSSION
We now wish to report a new and facile synthesis of 2-pyridones contain-
ing the sulfonamide moiety using a microwave oven based methodology
with the aim of finding compounds with promising biological activities.
The precursor, dimethyl 4-(methoxymethylene)-2-pentene dioate
2 was synthesized using a published procedure1 through the reaction
of coumalic acid 1 with acetyl chloride in methanol at refluxing tem-
perature (Scheme 1).
The reactivity of 2a,b with amines was studied in the aim to form
pyridone derivatives with potential biological activity. Thus the reac-
tion of compound 2 with p-substituted aniline9 gave one isomer of di-
enamino ester 3a–j. The structures of the latter products were based
on analytical and spectral data.
Compounds 3a–j underwent ready cyclization1 when irradiated in a
microwave oven in the presence of dimethyl formamide for 3 minutes
to give the corresponding N-substituted 5-carbomethoxy-2-pyridones
4a–j (Scheme 2).
The structures of these products were established on the basis of
their analytical and spectral data. All the synthesized compounds were
screened for antimicrobial activity against representative Gram posi-
tive and Gram negative bacteria, and fungi.
Antimicrobial Activity
Applying the agar plate diffusion technique,10some of the newly syn-
thesized compounds were screened in vitro for antimicrobial activity
SCHEME 1

5-Carbomethoxy-2-pyridone Derivatives Containing Sulfonamide Moiety 3147
SCHEME 2
against representative Gram positive bacteria (Staphylococcus au-
reus, Bacillus subtilis), Gram negative bacteria (Escherichia coli,
Pseudomonas aeruginosa), yeast, (Candida albicans), and fungi, (As-
pergillus niger). In this method a standard 5-mm diameter sterilized
filter paper disc impregnated with the compound (0.3 mg/0.1 ml of
dimethyl-formamide) was placed on an agar plate seeded with the
tested organism. The plates were incubated for 24 h at 37◦C for bacte-
ria and 28◦C for fungi. The zone of inhibition of bacterial and fungal
growth around the disc was observed. The screened results given in Ta-
ble I revealed that the synthesized compounds showed high or moderate
antimicrobial activity against tested Gram positive bacteria staphylo-
coccus aureus, (compounds number; 3a, 3c, 3g, 3h, 3i, 3j, 4a, 4b, 4c,
4g, 4h, 4i) and Bacillus subtilis (compounds number; 3c, 3h, 4a, 4b,
4c, 4e, 4i, 4j). Only six compounds (3c, 3h, 4a, 4b, 4c, 4i), showed
antimicrobial activity against both tested organisms, this is because
these compounds contain (R = PhCH2, C6H4Cl (p−), H, n-Pr, PhCH2,
C6H4NO2(o−)), respectively.
On the other hand, all synthesized compounds showed high (num-
ber; 3d, 3f, 3j, 4a, 4c, 4d, 4g, 4i, 4j) or moderate (number; 3a, 3b,
3c, 3e, 3g, 3h, 3i, 4b, 4e, 4f, 4h) antimicrobial activity against tested
Gram negative bacteria Escherichia coli. On the other hand no an-
timicrobial activity obtained against tested Gram negative bacteria

3148
F. El-Mariah and E. Nassar
TABLE I Antibacterial and Antifungal Activity
Staphylococ Bacillus Escherichia Pseudomonas Candida Aspergillus
No.
cus aureus subtilis
coli
aeruginosa albicans
nigar
3a
3b
3c
3d
3e
3f
3g
3h
3i
3j
4a
4b
4c
4d
4e
4f
++
−
−
−
++
++
−
−
−
−
−
−
+ + +
−
++
−
++
−
−
−
+ + +
++
−
−
−
−
−
−
−
−
−
−
+ + +
+
−
−
−
++
++
++
++
+ + +
++
++
−
−
−
−
−
+ + +
−
++
−
−
−
++
−
−
−
−
+ + +
+ + +
++
−
−
−
+ + +
++
++
−
−
−
−
−
−
−
+ + +
+ + +
++
−
−
−
−
−
−
−
++
−
−
−
−
−
+
−
−
−
4g
4h
4i
4j
++
++
++
−
−
+ + +
++
−
−
−
−
−
−
−
++
++
+ + +
−
+ + +
+ + +
+ + +
−
−
−
−
−
−
−
Ciprofloxacin
Fungicide
Nystin
+ + +
−
+ + +
−
−
−
+ + +
+ + +
Zone of inhibition: + = 10–15 mm; ++ = 15–20 mm; + + + = 20–25 mm; − = No
inhibition.
Pseudomonas aeruginosa. It should be mentioned here that (com-
pounds number 3a, 3c, 3g, 3h, 3i, 3j, 4a, 4b, 4c, 4e, 4g, 4h, 4i,
4j) showed antimicrobial activity against both tested Gram positive
and Gram negative bacteria, whereas the highest antimicrobial ac-
tivity was obtained by compound (4a), which contains (R=H). More-
over synthesized compounds did not show any antimicrobial activity
against both tested yeast, (Candida albicans) and fungi, (Aspergillus
nigar).
Finally, results of antimicrobial activity revealed that synthesized
compounds showed high antimicrobial activity against bacteria than
fungi. It could be concluded from these results that the biologi-
cally active compounds are nearly as active as standard antibiotic
Ciprofloxacin against the tested both Gram positive bacteria Staphy-
lococcus aureus and Bacillus subtilis and Gram negative bacteria

5-Carbomethoxy-2-pyridone Derivatives Containing Sulfonamide Moiety 3149
Escherichia coli and are completely inactive against tested yeast, (Can-
dida albicans) and fungi,(Aspergillus nigar).
EXPERIMENTAL
Melting points were determined in open glass capillaries and are un-
corrected. Elemental analyses were carried out in the microanalytical
laboratory of the Faculty of Science, Cairo, University. The IR spec-
tra of compounds were recorded on a Perkin-Elmer; spectrophotometer
model 1430 as potassium bromide pellets and frequencies are reported
in Cm−1. The mass spectra were recorded on a mass spectrometer HP
model MS 5988 El 70 eV. The 1H-NMR spectra were observed on Perkin-
Elmer R12B spectrometer and chemical shifts δ are in ppm relative to
internal TMS. Microwave oven (1000 watt, 30−80% of its total power),
input 230−240 volt 50 Hz, 1400 Watt. Output 2450 M. Hz 900 Watt.
Reactions were routinely followed by thin layer chromatography (TLC)
on silica gel F254 aluminum sheets (Merck). The spots were detected by
U.V irradiation at 254−336 nm. Compound 1 and 2 were synthesized
as reported previously.10,11
Synthesis of Dienamino Benzene Sulfonamido Esters
(3a-j)—General Procedure
P-substituted aniline (2.5 mmol) was added to a solution of dimethyl
4-(methoxymethylene)-2-pentenedioate 2a,b (2.5 mmol, 0.5 g) in
dimethylformamide (5 ml). The reaction mixture was stirred at room
temperature for 15 min, poured into water and extracted with ethyl
acetate. The organic layer was washed with brine and water, dried over
magnesium sulfate, evaporated under reduced pressure, to afford crude
solid product which was recrystallized from ethanol to give 3a–j.
Dimethyl (2E,4Z)-4-{[(4-sulfamoylphenyl) amino]
methylene}pent-2-enedioate (3a)
Yield (0.41 g, 82%), m.p. 210−211◦C; IR: 3369, 3300 (NH, Amine
and Sulfonamide), 3100, 851 (C H, Ar), 1760 (C O, Ester), 1658 (C C,
Alkene), 1595 (C C, Ar-ring), 1370 (S O, Asy.), 1156 (S O, Sym.) Cm−1
;
MS (m/z, %): 340 (M+, 1), 255 (2), 199 (2), 173 (10), 172 (100), 156 (43),
92 (13),. Anal. calcd. for C14H16N2O6S:C, 49.40; H, 4.74; N, 8.23; Found:
C, 49.70; H, 4.80; N, 8.40.

3150
F. El-Mariah and E. Nassar
Dimethyl (2E,4Z)-4-({[4-(propylsulfamoyl) phenyl]
amino}methylene)pent-2-enedioate (3b)
Yield (0.4 g, 80%), m.p. 124−126◦C; IR: 3468, 3375 (NH, Amine and
Sulfonamide), 3098, 835 (C H, Ar), 1734 (C O, Ester), 1632 (C C,
Alkene) 1595 (C C, Ar-ring), 1360 (S O, Asy.), 1161 (S O, Sym.) Cm−1
;
MS (m/z, %): 382 (M+, 5), 368 (11), 337 (13), 336 (7), 321 (7), 293 (9), 264
(13), 240 (100), 239 (37), 238 (9), 213 (30), 199 (20), 122 (53), 92 (42),
91 (21), 60 (38), 57 (68). 1H-NMR (DMSO-d6): δ 0.89−0.91 (t, 3H, CH3),
1.26−2.12 (m, 2H, CH2), 2.18−2.25 (t, 1H, NH),3.17−3.20 (t, 2H, CH2),
3.76 (s, 6H, 2OCH3), 4.0 (s, 1H, NH), 6.51−6.54 (dd, 2H, Ar), 6.68 (s,
1H, CH), 6.70−6.71 (d, 1H, CH), 7.56−7.59 (d, 1H, CH), 7.65−7.68
(dd, 2H, Ar). Anal calcd. for C17H22N2O6S: C, 53.39; H, 5.80; N, 7.33;
Found: C, 53.10; H, 5.90; N, 7.50.
Dimethyl (2E,4Z)-4-({[4-(benzylsulfamoyl)
phenyl]amino}methylene) pent-2-enedioate (3c)
Yield (0.37 g, 74%), m.p. 180−181◦C; IR: 3488, 3389 (NH, Amine
and Sulfonamide), 3075, 829 (C-H, Ar.), 1720 (C O, Ester), 1631 (C C,
Alkene), 1595 (C C, Ar-ring), 1388 (S O, Asy.), 1149 (S O, Sym.) Cm−1
;
MS (m/z, %): 431 (M++1, 2), 387 (2), 261 (2), 249 (3), 171 (2), 106 (4),
107 (7), 91 (10), 79 (14), 77 (8) 69 (100), 68 (20), 67 (31), 57 (62). Anal.
calcd. for C21H22N2O6S: C, 58.59; H, 5.15; N, 6.51; Found: C, 58.30; H,
5.00; N, 6.60.
Mimethyl (2E,4Z)-4-({[4-(phenylhydrazinosulfamoyl)
phenyl]amino}methylene) pent-2-enedioate (3d)
Yield (0.39g, 78%), m.p. 168−170◦C; IR: 3567, 3367(NH, Amine and
Sulfonamide), 3060, 830 (C-H, Ar), 1725 (C O, Ester), 1628 (C C,
Alkene), 1594 (C C, Ar-ring), 1400 (S O, Asy.), 1153 (S O, Sym.) Cm−1
;
MS (m/z, %): 431 (M+, 14), 156 (34), 108 (28), 93 (19), 92 (42), 77 (72), 65
(100). Anal. calcd. for C20H21N3O6S: C, 55.67; H, 4.91; N, 9.74; Found:
C, 55.90; H, 5.00; N, 9.60.
Dimethyl (2E,4Z)-4-({[4-(phenylsulfamoyl) phenyl]
amino}methylene)pent-2-enedioate (3e)
Yield (0.4 g, 80%), m.p. 181−182◦C; IR: 3476, 3350 (NH, Amine
and Sulfonamide), 3040, 830 (C-H, Ar), 1720 (C O, Ester), 1640 (C C
Alkene) 1595 (C C, Ar-ring), 1316 (S O, Asy.) 1151 (S O, Sym.) Cm−1
;
MS (m/z, %): 416 (M+, 5), 403 (18), 347(7), 306 (9), 280 (17), 254(12),
238 (7); 165 (29), 106 (100). Anal calcd. for C20H20N2O6S: C, 57.68; H,
4.84, N, 6.73; Found: C, 57.40; H, 4.90; N, 6.90.

5-Carbomethoxy-2-pyridone Derivatives Containing Sulfonamide Moiety 3151
Dimethyl(2E,4Z)-4-[({4-[(4- methylphenyl)sulfamoyl]
phenyl}amino) methylene]pent-2- enedioate (3f)
Yield (0.35g, 70%), m.p. 180−182◦C; IR: 3413, 3344 (NH, Amine
and Sulfonamide), 3024, 811 (C-H, Ar), 1734 (C O, Ester), 1635 (C C,
Alkene), 1596 (C C, Ar-ring), 1320 (S O, Asy.), 1154 (S O, Sym.) Cm−1
;
MS (m/z, %): 430 (M+, 11), 357, (12), 262 (92), 156 (57), 106 (100), 92
(77), 77 (92).1H NMR (DMSO-d6): δ 2.49 (s, 3H, CH3), 3.63 (s, 6H,
2OCH3), 4.1 (s, 1H, NH), 4.3 (s, 1H, NH), 6.53–6.55 (d, 1H, CH),
6. –6.53 (dd, 2H, Ar), 6.58−6.60 (dd, 2H, Ar),6.88−6.92 (dd, 2H, Ar),
6.93 (s, 1H, CH), 7.38−7.41(d, 1H, CH), 7.45−7.48 (dd, 2H, Ar).
Anal.calcd.forC21H22 N2O6S: C, 58.59; H, 5.15; N, 6.51; Found: C, 58.90;
H, 5.30; N, 6.40.
Dimethyl (2E,4Z)-4-[({4-[(4- methoxyphenyl) sulfamoyl]
phenyl}amino)methylene]pent-2- enedioate (3g)
Yield (0.43g, 86%), m.p. 188−189◦C; IR: 3487, 3388 (NH, Amine
and Sulfonamide), 3075, 829 (C-H, Ar), 1721 (C O, Ester), 1632 (C C,
Alkene), 1595 (C C, Ar-ring), 1388 (S O, Asy.), 1148 (S O, Sym.) Cm−1
;
MS (m/z, %): 447 (M+, 20), 364 (25), 266 (22), 123 (44), 122 (100), 78
1
(48) H NMR (DMSO-d6):δ 3.30 (s, 3H, OCH3), 3.65 (s, 6H, 2OCH3),
3.70 (s, 1H, NH), 3.80 (s, 1H, NH), 6.45−6.48 (d, 1H, CH), 6.50 – 6.53
(dd, 2H, Ar), 6.55−6.58 (dd, 2H, Ar), 6.70−6.74 (dd, 2H, Ar), 6.95 (s, 1H,
CH ), 7.25− 7.27 (d, 1H, CH),7.30−7.33 (dd, 2H, Ar). Anal. calcd. for
C21H22N2O7S: C, 56.49; H, 4.97; N, 6.28; Found: C, 56.10;H, 4.90; N,
6.10.
Dimethyl (2E,4Z)-4-[({4-[(4- chlorophenyl) sulfamoyl]
phenyl}amino)methylene]pent-2-enedioate (3h)
Yield (0.42 g, 84%), m.p. 190−191◦C; IR: 3416, 3344 (NH, Amine
and Sulfonamide), 3100, 826(C-H, Ar), 1720 (C O, Ester), 1640 (C C,
Alkene), 1595 (C C, Ar-ring), 1312 (S O, Asy.), 1148 (S O, Sym.) Cm−1
;
MS (m/z,%): 450 (M+, 2), 282 (22), 156 (100), 126 (17), 92 (61),. Anal.
calcd. for C20H19ClN2O6S: C, 53.27; H, 4.25; N, 6.21; Found: C, 53.50;
H, 4.40; N, 6.00.
Dimethyl(2E,4Z)-4-[({4-[(2- nitrophenyl)sulfamoyl]
phenyl}amino)methylene]pent-2-enedioate (3i)
Yield (0.41g, 82%), m.p. 125−127◦C; IR: 3566, 3399 (NH, Amine
and Sulfonamide), 2955, 844 (C-H, Ar), 1733 (C O, Ester), 1600 (C C,
Alkene), 1595 (C C, Ar-ring), 1389 (S O, Asy.), 1162 (S O, Sym.) Cm−1
;
MS (m/z, %): 461 (M+, 2), 387 (4), 372 (3), 343 (4), 317 (5) 293 (6), 277(6),
221 (100), 140 (10), 122 (8), 77 (19), 76 (16), 59 (85). Anal. calcd. for

3152
F. El-Mariah and E. Nassar
C20H19N3O8S: C, 52.06; H, 4.15; N, 9.11; Found: C, 52.30; H, 4.10, N,
9.30.
Dimethyl(2E,4Z)-4-[({4-[(4- nitrophenyl)sulfamoyl]
phenyl}amino)methylene]pent-2-enedioate (3j)
Yield (0.45g, 90%), m.p. 149−150◦C; IR: 3413, 3342 (NH, Amine
and Sulfonamide), 3075, 847 (C H, Ar), 1721 (C O, Ester), 1631 (C C,
Alkene), 1596 (C C, Ar-ring), 1345 (S O, Asy.), 1156 (S O, Sym.) Cm−1
;
MS (m/z, %): 464 (M++3, 0.4), 293 (13), 137 (3), 92 (100). Anal. calcd.
for C20H19N3O8S: C, 52.06; H, 4.15, N, 9.11; Found: C, 51.80; H, 4.30;
N, 8.90.
Synthesis of 2-Pyridones (4a-j)—General Procedure
Enamino esters 3a–j (1.0 mmol) in (0.1 ml) dimethyl-formamide was
irradiated in a microwave oven for 3 minutes. the reaction was rou-
tinely checked by thin layer chromatography (TLC). The reaction
mixture was extracted with diethyl ether, washed with brine, wa-
ter and dried over anhydrous magnesium sulfate. The organic layer
was evaporated. The residue was recrystallized from ethanol to give
(4a–j).
Methyl 2-oxo-1-(4-sulfamoylphenyl)-1,2-dihydropyridine-5-
carboxylate (4a)
Yield (0.28 g, 90%), m.p. 120−122◦C; IR: 3348 (NH, Sulfonamide),
3096, 834 (C-H, Ar), 1726 (C O, Ester), 1594 (C C, Ar-ring), 1336 (S O,
Asy), 1159 (S O, Sym.) Cm−1; MS (m/z,%): 308 (M+, 7), 279 (13), 249
(13), 185 (6), 172 (23), 156 (28), 149 (100).1H NMR (DMSO-d6): δ 2.25
(s, 2H, NH2), 3.76 (s, 3H, OCH3), 6.56−6.59 (d, 1H, CH), 6.85−7.15 (d,
1H, CH),7.85−7.88 (dd, 2H, Ar), 7.92−7.95 (dd, 2H, Ar),8.30 (s, 1H,
CH). Anal. calcd. for C13H12N2O5S: C, 50.64; H, 3.92; N, 9.09; Found:
C, 50.90; H, 4.00; N, 9.20.
Methyl 2-oxo-1-[4-(propylsulfamoyl)
phenyl]-1,2-dihydropyridine-5-carboxylate (4b)
Yield (0.30 g, 85.7%), m.p. 105−106◦C; IR: 3437, 3370 (NH, Sulfon-
amide), 3065, 834 (C H, Ar), 1703 (C O, Ester), 1632 (C C, Alkene),
1596 (C C, Ar-ring), 1335 (S O, Asy.), 1161 (S O, Sym.) Cm−1;MS
(m/z, %): 353 (M++3, 12), 227 (21), 225 (11), 213 (34), 199 (19), 123
(36), 69 (100). 1H NMR (DMSO-d6): δ 1.27−1.32 (t, 3H, CH3), 1.42−1.66
(m, 2H, CH2), 2.22 (s, 1H, NH), 2.96−3.10 (t, 2H, CH2), 3.76 (s, 3H,
OCH3),6.63−6.66 (d, 1H, CH), 6.69−6.71 (d, 1H, CH), 7.57−7.60
(dd, 2H, Ar), 7.69−7.72 (dd, 2H, Ar), 8.42 (s, 1H, CH). Anal. calcd. for

5-Carbomethoxy-2-pyridone Derivatives Containing Sulfonamide Moiety 3153
C16H18N2O5S: C, 54.84; H, 5.18; N, 8.00; Found: C, 54.60; H, 5.10; N,
8.10.
Methyl 1-[4-(benzylsulfamoyl)phenyl]-2-oxo-1,2-
dihydropyridine-5-carboxylate (4c)
Yield (0.38 g, 95%), m.p. 78−80◦C; IR: 3378 (NH, Sulfonamide), 829
(C-H, Ar), 1725 (C O, Ester), 1657 (C C, Alkene), 1596 (C C, Ar-ring),
1328 (S O, Asy.), 1150 (S O, Sym.) Cm−1; MS (m/z, %): 398 (M+, 3),
369 (6), 275 (6), 246 (2), 169 (2), 122 (100), 106 (2), 105 (8). Anal. calcd.
for C20H18N2O5S: C, 60.29; H, 4.55; N, 7.03; Found: C, 60.00; H, 4.60;
N, 6.90.
Methyl 2-oxo-1-{4-[(2- phenylhydrazino)
sulfonyl]phenyl}-1,2-dihydropyridine-5-carboxylate (4d)
Yield (0.39 g, 97.5%); m.p. 154−155◦C; IR: 3424, 3330 (NH, Sulfon-
amide), 835 (C-H, Ar), 1734 (C O, Ester), 1653 (C C, Alkene), 1595
(C C, Ar-ring), 1376 (S O, Asy.), 1162 (S O, Sym.) Cm−1; MS (m/z,
%): 399 (M+; 0.5), 261 (1), 248 (31), 171 (1), 108 (51), 107 (5), 93 (26), 92
(95), 77 (8), 65 (100). Anal. calcd. for C19H17N3O5S: C, 57.13; H, 4.29;
N, 10.52; Found: C, 56.90; H, 4.20; N, 10.40.
Methyl 2-oxo-1-[4(phenylsulfamoyl)phenyl]-1,2-
dihydropyridine-5-carboxylate (4e)
Yield (0.35g, 92%), m.p. 160−161◦C; IR: 3419, 3350 (NH, Sulfon-
amide), 3100, 831 (C H, Ar), 1719 (C O, Ester), 1630 (C C, Alkene),
1595 (C C, Ar-ring), 1317 (S O, Asy.), 1154 (S O, Sym.) Cm−1; MS
(m/z, %): 384 (M+, 0.1), 248 (22), 156 (62), 92 (62), 77 (2), 65 (100).
Anal. calcd. for C19H16N2O5S: C, 59.36; H, 4.20, N, 7.29; Found: C,
59.60; H, 4.30; N, 7.40.
Methyl 1-{4-[(4- methylphenyl) sulfamoyl]phenyl}-2-oxo-
1,2-dihydropyridine-5-carboxylate (4f)
Yield (0.36 g, 90%), m.p. 140−141◦C; IR: 3471, 3378 (NH, Sulfon-
amide), 3033, 821 (C H, Ar), 1719 (C O, Ester), 1668 (C C, Alkene),
1594 (C C, Ar-ring), 1322 (S O, Asy.), 1154 (S O, Sym.) Cm−1; MS
(m/z, %): 398 (M+; 37), 276 (34) 253 (34), 170 (42), 106 (100), 77 (61), 59
1
(42). H NMR (DMSO-d6): δ 2.3 (s, 3H, CH3), 3.75 (s, 3H, OCH3), 4.11
(s, 1H, NH), 6.42−6.46 (d, 1H, CH), 6.49−6.52 (dd, 2H, Ar), 681−6.83
(dd, 2H, Ar), 6.93−6.95 (d, 1H, CH), 7.84−7.86 (dd, 2H, Ar), 7.91−7.93
(dd, 2H, Ar) 8.16 (s, 1H, CH),.Anal. calcd. for C20H18N2O5S: C, 60.29;
H, 4.55; N, 7.03; Found: C, 6.00; H, 4.50; N, 7.20.

3154
F. El-Mariah and E. Nassar
Methyl 1-{4-[(4-methoxyphenyl) sulfamoyl]phenyl}-2-oxo-
1,2-dihydropyridine-5-carboxylate (4g)
Yield (0.39g, 95%), m.p. 165−167◦C; IR: 3486, 3388 (NH, Sulfon-
amide), 3074, 829 (C H, Ar), 1724 (C O, Ester), 1666 (C C, Alkene),
1595 (C C, Ar-ring), 1389 (S O, Asy.), 1149 (S O, Sym.) Cm−1; MS
(m/z, %): 414 (M+, 0.44), 123 (13), 122 (100), 108 (12), 107 (3), 77
(3), 65 (62).1H NMR (DMSO-d6): δ 3.73 (s, 3H, OCH3), 3.76 (s, 3H,
OCH3), 4.0 (s, 1H, NH), 6.46−6.48 (dd, 2H, Ar), 6.50−6.52 (d, 1H,
CH), 6.55−6.58 (dd, 2H, Ar),6.93−6.95 (d, 1H, CH), 7.70−7.72
(dd, 2H, Ar), 7.78−7.80 (dd, 2H, Ar), 7.81 (s, 1H, CH). Anal. calcd.
for C20H18N2O6S: C, 57.96; H, 4.38; N, 6.76; Found: C, 57.70; H, 4.30;
N, 6.80.
Methyl 1-{4-[(4- chlorophenyl) sulfamoyl]phenyl}-2-oxo-
1,2-dihydropyridine-5-carboxylate (4h)
Yield (0.40 g, 95%), m.p. 135−36◦C; IR: 3469, 3378 (NH, Sul-
fonamide), 3100, 829 (C H, Ar), 1727 (C O, Ester), 1662 (C C,
Alkene), 1594 (C C, Ar-ring), 1389 (S O, Asy.), 1156 (S O, Sym.)
Cm−1; MS (m/z, %): 418 (M+, 1%), 361 (1), 297 (1), 282 (11), 190
(2), 126 (23), 111 (4), 92 (100), 77 (1), 65 (65). Anal. calcd. for
C19H15ClN2O5S: C, 54.48; H, 3.61; N, 6.69; Found: C, 54.70; H, 3.70;
N, 6.80.
Methyl 1-{4-[(2- nitrophenyl) sulfamoyl]phenyl}-2-oxo-
1,2-dihydropyridine-5-carboxylate (4i)
Yield (0.37g, 74%), m.p. 90−91◦C; IR: 3448, 3374 (NH, Sulfonamide),
3100, 842 (C H, Ar), 1723 (C O, Ester), 1655 (C C, Alkene), 1580
(C C, Ar-ring), 1346 (S O, Asy.), 1162 (S O, sym.) Cm−1; MS (m/z, %):
429 (M+, 2), 370 (5), 305 (5), 278 (5), 201 (5), 138 (43), 137 (28), 122 (8),
77 (16), 69 (100). Anal. calcd. for C19H15N3O7S: C, 53.14; H, 3.52; N,
9.79; Found: C, 53.40; H, 3.60; N, 9.90.
Methyl 1-{4-[(4- nitrophenyl) sulfamoyl]phenyl}-2-oxo-
1,2-dihydropyridine-5-carboxylate (4j)
Yield (0.40 g, 93%), m.p. 120−121◦C; IR: 3381 (NH, Sulfonamide),
3084, 848 (C H, Ar), 1734 (C O, Ester), 1654 (C C, Alkene), 1596
(C C, Ar-ring), 1342 (S O, Asy.), 1157 (S O, Sym.) Cm−1; MS (m/z,
%): 429 (M+, 23), 414 (27), 370 (27), 317 (40), 276 (23), 201 (33), 137
(27) 122 (30), 76 (27), 54 (100). Anal. calcd. for C19H15N3O7S: C, 53.14;
H, 3.52; N, 9.79; Found: C, 52.90; H, 3.60; N, 9.60.

5-Carbomethoxy-2-pyridone Derivatives Containing Sulfonamide Moiety 3155
CONCLUSION
An expedient route has been developed for the preparation of biologi-
cally active N-substituted 5-carbomethoxy-2-pyridones containing sul-
fonamide moiety by cyclizing of dienamino esters using a microwave
oven based methodology.
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