J. Chil. Chem. Soc., 57, Nº 1 (2012)
(C-12), 130.2 (C-16), 130.5 (C-3a), 131.6 (C-14), 132.7 (C-13), 133.1 (C-15),
134.8 (C-6), 135.7 (C-3), 137.5 (C-11), 140.7 (C-7a),165.8 (C-2’), 173.3 (C-
4”); FAB-Mass (m/z): 504 [M+]; Anal. Calcd. for C20H N5O4SBr: C, 47.62, H,
3.52, N, 13.88 %; found C, 47.59, H, 3.48, N, 13.79 %1.8
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(4-nitrophenyl)-4-oxo-1,3-
thiazolidine-carboxamide (4h):
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(phenyl)-4-oxo-5-
(benzylidene)-1,3-thiazolidine-carboxamide (5a):
Yield: 62%; m.p. 162-163 ºC; IR (cm-1): 670 (C-S-C), 885 (C-N), 1343
(N-CH2), 1536 (NO2), 1666 (C=O), 1741 (CO cyclic), 1457, 2854, 2902 (CH2),
2941 (C=CH), 3038 (CH-Ar), 3366 (NH); 1H NMR (CDCl3, 300 MHz) δ: 2.12-
2.16 (m, 2H, H-9), 3.43-3.49 (m, 2H, H-10), 4.16 (t, 2H, J = 7.40 Hz, H-8),
5.10 (s, 1H, H-2”), 5.69 (s, 1H, H-1’), 6.52 (s, 1H, H-17), 7.77-8.31 (m, 14H,
Ar-H);13C NMR (CDCl3, 75 MHz) δ: 32.8 (C-9), 40.1 (C-10), 54.3 (C-8), 60.5
(C-2”), 117.6 (C-4), 123.2 (C-7), 125.4 (C-5), 127.3 (C-19 and C-23), 128.1
(C-12 and C-16), 129.2 (C-3a), 129.7 (C-20 and C-22), 130.5 (C-14), 131.4 (C-
13 and C-15), 132.1 (C-18), 134.8 (C-6), 135.7 (C-3), 137.6 (C-11), 138.2 (C-
17), 140.7 (C-5”), 142.3 (C-7a), 162.0 (C-2’), 170.7 (C-4”); FAB-Mass (m/z):
513 [M+]; Anal. Calcd. for C27H23N5O4S: C, 63.14, H, 4.51, N, 13.63 %; found
C, 63.12, H, 4.49, N, 13.57 %.
Yield: 66%; m.p. 177-179 ºC; IR (cm-1): 673 (C-S-C), 893 (C-N), 1349 (N-
CH2), 1538 (NO2), 1549 (C=C), 1666 (C=O), 1746 (CO cyclic), 1459, 2854,
2897 (CH2), 2955 (S-CH2), 3036 (CH-Ar), 3368 (NH); 1H NMR (CDCl3, 300
MHz) δ: 2.20-2.25 (m, 2H, H-9), 3.39 (s, 2H, H-5”), 3.43-3.49 (m, 2H, H-10),
4.21 (t, 2H, J = 7.45 Hz, H-8), 5.36 (s, 1H, H-2”), 5.70 (s, 1H, H-1’), 7.26-7.84
(m, 8H, Ar-H);13C NMR (CDCl , 75 MHz) δ: 32.2 (C-9), 36.9 (C-5”), 40.3 (C-
10), 51.8 (C-8), 57.2 (C-2”), 1183.6 (C-4), 123.4 (C-5), 124.7 (C-7), 127.6 (C-12
and C-16), 128.8 (C-3a), 129.9 (C-14), 130.4 (C-13 and C-15), 135.7 (C-11),
132.6 (C-6), 133.7 (C-3), 143.1 (C-7a), 162.4 (C-2’), 174.3 (C-4”); FAB-Mass
(m/z): 470 [M+]; Anal. Calcd. for C20H18N6O6S: C, 51.06, H, 3.85, N, 17.86 %;
found C, 51.00, H, 3.78, N, 17.79 %.
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(4-chlorophenyl)-4-oxo-5-(4-
chloro benzylidene)-1,3-thiazolidine-carboxamide (5b):
Yield: 64%; m.p. 179-180 ºC; IR (cm-1): 672 (C-S-C), 744 (C-Cl), 887 (C-
N), 1345 (N-CH2), 1544 (NO2), 1566 (C=CH), 1672 (C=O), 1742 (CO cyclic),
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(3-nitrophenyl)-4-oxo-1,3-
thiazolidine-carboxamide (4i):
1
1462, 2861, 2906 (CH2), 2947 (C=CH), 3040 (CH-Ar), 3370 (NH); H NMR
Yield: 64%; m.p. 180-181 ºC; IR (cm-1): 666 (C-S-C), 887 (C-N), 1350 (N-
CH2), 1539 (NO2), 1546 (C=C), 1669 (C=O), 1747 (CO cyclic), 1456, 2850,
2905 (CH2), 2957 (S-CH2), 3037 (CH-Ar), 3369 (NH); 1H NMR (CDCl3, 300
MHz) δ: 2.19-2.24 (m, 2H, H-9), 3.28-3.33 (m, 2H, H-10), 3.37 (s, 2H, H-5”),
4.20 (t, 2H, J = 7.40 Hz, H-8), 5.41 (s, 1H, H-2”), 5.69 (s, 1H, H-1’), 7.29-7.81
(m, 8H, Ar-H); 13C NMR (CDCl3, 75 MHz) δ: 33.4 (C-9), 37.4 (C-5”), 41.6
(C-10), 49.7 (C-8), 58.1 (C-2”), 119.6 (C-4), 124.8 (C-7), 125.6 (C-5), 128.4
(C-12), 129.5 (C-3a), 129.7 (C-16), 130.7 (C-14), 131.6 (C-13), 133.5 (C-6),
133.7 (C-15), 134.2 (C-3), 136.8 (C-11), 142.7 (C-7a), 163.4 (C-2’), 174.5 (C-
4”); FAB-Mass (m/z): 470 [M+]; Anal. Calcd. for C20H18N6O6S : C, 51.06, H,
3.85, N, 17.86 %; found C, 51.04, H, 3.80, N, 17.81%.
(CDCl , 300 MHz) δ: 2.15-2.20 (m, 2H, H-9), 3.45-3.51 (m, 2H, H-10), 4.20
(t, 2H,3J = 7.40 Hz, H-8), 5.16 (s, 1H, H-2”), 5.75 (s, 1H, H-1’), 6.57 (s, 1H,
H-17), 7.79-8.37 (m, 12H, Ar-H);13C NMR (CDCl3, 75 MHz) δ: 32 (C-9), 40.6
(C-10), 54.9 (C-8), 60.7 (C-2”), 118.2 (C-4), 123.5 (C-7), 126.5 (C-5), 127.7
(C-19 and C-23), 128.4 (C-12 and C-16), 129.4 (C-3a), 129.8 (C-20 and C-22),
131.3 (C-14), 131.9 (C-13 and C-15), 132.6 (C-18), 136.4 (C-3), 134.4 (C-6),
137.6 (C-11), 141.2 (C-17), 142.3 (C-5”), 142.9 (C-7a), 162.5 (C-2’), 171.1
(C-4”); FAB-Mass (m/z): 582 [M+]; Anal. Calcd. for C27H21N5O4SCl2: C, 55.67,
H, 3.63, N, 12.02 %; found C, 55.57, H, 3.55, N, 11.95 %.
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(3-chloro phenyl)-4-oxo-5-(3-
chloro benzylidene)-1,3-thiazolidine-carboxamide (5c):
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(2-nitrophenyl)-4-oxo-1,3-
thiazolidine-carboxamide (4j):
Yield: 62%; m.p. 175-176 ºC; IR (cm-1): 670 (C-S-C), 749 (C-Cl), 888 (C-
N), 1346 (N-CH2), 1530 (NO2), 1578 (C=CH) 1647 (C=O), 1743 (CO cyclic),
1
Yield: 68%; m.p. 178-179 ºC; IR (cm-1): 675 (C-S-C), 889 (C-N), 1347 (N-
CH2), 1541 (NO2), 1548 (C=C), 1668 (C=O), 1748 (CO cyclic), 1460, 2852,
2902 (CH2), 2965 (S-CH2), 3040 (CH-Ar), 3370 (NH); 1H NMR (CDCl3, 300
MHz) δ: 2.24-2.29 (m, 2H, H-9), 3.29 (s, 2H, H-5”), 3.34-3.39 (m, 2H, H-10),
4.26 (t, 2H, J = 7.50 Hz, H-8), 5.22 (s, 1H, H-2”), 5.72 (s, 1H, H-1’), 7.34-7.92
(m, 8H, Ar-H); 13C NMR (CDCl3, 75 MHz) δ: 34.7 (C-9), 37.1 (C-5”), 41.5
(C-10), 48.6 (C-8), 60.4 (C-2”), 119.7 (C-4), 126.2 (C-7), 127.3 (C-5), 129.6
(C-12), 130.4 (C-3a), 130.7 (C-16), 131.3 (C-14), 132.8 (C-13), 134.1 (C-15),
135.3 (C-3), 136.9 (C-6), 137.3 (C-11), 142.8 (C-7a), 163.1 (C-2’), 175.7 (C-
4”); FAB-Mass (m/z): 470 [M+]; Anal. Calcd. for C20H18N6O6S: C, 51.06, H,
3.85, N, 17.86 %; found C, 51.01, H, 3.82, N, 17.85 %.
1450, 2839, 2923 (CH2), 2946 (C=CH), 3047 (CH-Ar), 3362 (NH); H NMR
(CDCl , 300 MHz) δ: 2.19-2.24 (m, 2H, H-9), 3.46-3.50 (m, 2H, H-10), 4.15
(t, 2H,3J = 7.50 Hz, H-8), 5.22 (s, 1H, H-2”), 5.74 (s, 1H, H-1’), 6.65 (s, 1H,
H-17), 7.85-8.39 (m, 12H, Ar-H); 13C NMR (CDCl , 75 MHz) δ: 35.8 (C-9),
44.1 (C-10), 49.3 (C-8), 60.9 (C-2”), 122.6 (C-4), 3124.2 (C-7), 128.4 (C-5),
128.7 (C-19), 128.9 (C-23), 129.1 (C-12), 129.8 (C-16), 130.2 (C-3a), 130.7
(C-20), 131.2 (C-22), 131.8 (C-14), 132.2 (C-13), 132.7 (C-15), 133.1 (C-18),
135.3 (C-6), 136.6 (C-3), 138.6 (C-11), 140.6 (C-17), 141.3 (C-7a), 143.7
(C-5”), 166.0 (C-2’), 173.4 (C-4”); Mass (FAB) 582 [M+]; Anal. Calcd. for
C27H21N O4SCl2: C, 55.67, H, 3.63, N, 12.02 %; found C, 55.59, H, 3.60, N,
11.98 %5.
General methods for the synthesis of compounds 5(a-j):
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(2-chloro phenyl)-4-oxo-5-(2-
chloro benzylidene)-1,3-thiazolidine-carboxamide (5d):
The compound 4a (0.007 mole) and benzaldehyde (0.007 mole) in
ethanol (50 ml) in the presence of CH3CH2ONa were allowed to react at room
temperature. The reaction mixture was first stirred on a magnetic stirrer for
about 2.00 hours followed by reflux on a steam bath for about 4.30 hours. The
completion of the reaction was monitored by silica gel-G coated TLC plates.
The product was filtered and cooled at room temperature. The filtered product
was purified over a silica gel packed column chromatography using CH OH :
CHCl (7 : 3 v/v) as eluant as eluant (50 ml). The purified product was3dried
under3vacuo and recrystallized from acetone at room temperature to furnish
compound 5a (Figure 5).
Yield: 68%; m.p. 172-173 ºC; IR (cm-1): 676 (C-S-C), 741 (C-Cl), 890 (C-
N), 1347 (N-CH2), 1541 (NO2), 1568 (C=CH), 1667 (C=O), 1744 (CO cyclic),
1
1464, 2856, 2903 (CH2), 2949 (C=CH), 3042 (CH-Ar), 3372 (NH); H NMR
(CDCl , 300 MHz) δ: 2.22-2.27 (m, 2H, H-9), 3.54-3.59 (m, 2H, H-10), 4.22
(t, 2H,3J = 7.50 Hz, H-8), 5.18 (s, 1H, H-2”), 5.77 (s, 1H, H-1’), 6.67 (s, 1H,
H-17), 7.83-8.40 (m, 12H, Ar-H); 13C NMR (CDCl , 75 MHz) δ: 36.5 (C-9),
43.4 (C-10), 50.0 (C-8), 57.3 (C-2”), 119.6 (C-4), 3125.5 (C-7), 126.4 (C-5),
128.3 (C-19), 128.7 (C-23), 129.4 (C-12), 129.7 (C-16), 130.2 (C-3a), 130.9
(C-20), 131.1 (C-22), 131.7 (C-14), 132.4 (C-13), 132.8 (C-15), 133.6 (C-18),
135.8 (C-6), 137.7 (C-3), 139.6 (C-11), 141.5 (C-17), 141.7 (C-7a), 143.8 (C-
5”), 163.7 (C-2’), 171.8 (C-4”); FAB-Mass (m/z): 582 [M+]; Anal. Calcd. for
C27H21N O4SCl2: C, 55.67, H, 3.63, N, 12.02 %; found C, 55.64, H, 3.57, N,
12.00 %5.
Compounds 5 (b-j) have also been synthesized by using similar method
as above.
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(4-bromo phenyl)-4-oxo-5-(4-
bromo benzylidene)-1,3-thiazolidine-carboxamide (5e):
Yield: 64%; m.p. 169-171 ºC; IR (cm-1): 679 (C-S-C), 891 (C-N), 1352
(N-CH2), 1542 (NO2), 1572 (C=CH), 1670 (C=O), 1746 (CO cyclic), 1465,
2859, 2904 (CH2), 2945 (C=CH), 3044 (CH-Ar), 3375 (NH); 1H NMR (CDCl3,
300 MHz) δ: 2.23-2.28 (m, 2H, H-9), 3.49-3.55 (m, 2H, H-10), 4.27 (t, 2H, J =
7.40 Hz, H-8), 5.15 (s, 1H, H-2”), 5.78 (s, 1H, H-1’), 6.68 (s, 1H, H-17), 7.81-
8.32 (m, 12H, Ar-H); 13C NMR (CDCl3, 75 MHz) δ: 33.7 (C-9), 41.6 (C-10),
51.3 (C-8), 61.7 (C-2”), 121.6 (C-4), 123.6 (C-7), 125.5 (C-5), 129.3 (C-19
and C-23), 130.3 (C-12 and C-16), 130.9 (C-3a), 131.7 (C-20 and C-22), 132.5
(C-14), 133.6 (C-13 and C-15), 134.5 (C-18), 136.6 (C-6), 138.7 (C-3), 139.7
(C-17), 140.4 (C-11), 141.6 (C-7a), 143.5 (C-5”), 163.8 (C-2’), 171.5 (C-4”);
Mass (FAB) 671 [M+]; Anal. Calcd. for C H21N5O4SBr2: C, 48.30, H, 3.15, N,
10.43 %; found C, 48.21, H, 3.14, N, 10.3297 %.
N-[3-(1H-6-nitroindazol-1-yl)-propyl]-2-(3-bromophenyl)-4-oxo-5-(3-
Figure 5: Structure of compound 5(a-j).
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