314
R. K. Bhatt et al.
CDCl3): d = -2.90 (s, 2H, internal NH), 3.91 (d,
J = 15.9 Hz, 1H, SCH2CO), 4.03 (d, J = 15.9 Hz, 1H,
SCH2CO), 6.78 (s, 1H, CH), 7.37–7.26 (m, 2H, ArH), 7.43
(d, J = 8.1 Hz, 1H, ArH), 7.54 (d, J = 6.9 Hz, 1H, ArH),
7.71–7.69 (m, 11H, meso-ArH), 8.07 (d, J = 8.1 Hz, 2H,
meso-ArH), 8.13 (d, J = 5.7 Hz, 6H, meso-ArH), 8.64 (d,
J = 4.8 Hz, 2H, b-pyrrolic H), 8.76 (s, 6H, b-pyrrolic H)
ppm; 13C NMR (100 MHz, CDCl3): d = 33.16, 64.53,
118.09, 120.19, 120.83, 121.89, 126.68, 127.74, 128.35,
129.87, 130.65, 134.53, 134.99, 137.03, 138.02, 140.79,
142.06, 170.69 ppm; HRMS (ESI): [M]? calcd for
C53H36ClN5OS 825.2329, found 825.2318.
(300 MHz, CDCl3): d = -2.81 (s, 2H, internal NH),
3.97 (d, J = 15.6 Hz, 1H, SCH2CO), 4.17 (d,
J = 14.1 Hz, 1H, SCH2CO), 6.15 (s, 1H, CH), 7.38 (d,
J = 8.1 Hz, 2H, ArH), 7.43 (d, J = 7.8 Hz, 2H, meso-
ArH), 7.62 (d, J = 8.1 Hz, 2H, ArH), 7.75–7.72 (m, 9H,
meso-ArH), 8.00 (d, J = 8.4 Hz, 2H, meso-ArH), 8.18–
8.17 (m, 6H, meso-ArH), 8.58 (d, J = 4.5 Hz, 2H,
b-pyrrolic H), 8.80 (d, J = 4.8 Hz, 2H, b-pyrrolic H),
8.84 (s, 4H, b-pyrrolic H) ppm; 13C NMR (100 MHz,
CDCl3): d = 33.48, 64.70, 118.40, 120.31, 120.55, 122.95,
126.01, 126.70, 127.28, 127.77, 131.05, 134.52, 134.93,
136.75, 140.71, 141.95, 143.43, 170.97 ppm; HRMS (ESI):
[M ? H]? calcd for C54H37F3N5OS 860.2671, found
860.2670.
2-(4-Nitrophenyl)-3-[4-(10,15,20-triphenylporphyrin-5-
yl)phenyl]thiazolidin-4-one (4b, C53H36N6O3S)
ꢀ
Yield 85%; IR (KBr): m = 1,702, 1,525, 1,473, 1,348, 966,
2-(4-Bromophenyl)-3-[4-(10,15,20-triphenylporphyrin-5-
yl)phenyl]thiazolidin-4-one (4e, C53H36BrN5OS)
1
802, 734 cm-1; H NMR (300 MHz, CDCl3): d = -2.83
ꢀ
(s, 2H, internal NH), 3.99 (d, J = 14.1 Hz, 1H, SCH2CO),
4.09 (d, J = 14.1 Hz, 1H, SCH2CO), 6.35 (s, 1H, CH),
7.50 (d, J = 8.4 Hz, 2H, ArH), 7.60 (d, J = 8.7 Hz, 2H,
meso-ArH), 7.80–7.72 (m, 9H, meso-ArH), 8.09 (d,
J = 8.4 Hz, 2H, meso-ArH), 8.21–8.17 (m, 6H, meso-
ArH), 8.28 (d, J = 8.4 Hz, 2H, ArH), 8.62 (d, J = 4.8 Hz,
2H, b-pyrrolic H), 8.81 (d, J = 4.8 Hz, 2H, b-pyrrolic H),
8.84 (s, 4H, b-pyrrolic H) ppm; 13C NMR (100 MHz,
CDCl3): d = 33.53, 64.24, 118.16, 120.38, 120.53, 122.84,
124.48, 126.71, 127.76, 131.17, 134.50, 135.35, 136.63,
141.08, 141.90, 146.92, 148.21, 170.89 ppm; HRMS (ESI):
[M]? calcd for C53H36N6O3S 836.2570, found 836.2566.
Yield 90%; IR (Nujol): m = 1,695, 1,595, 1,462, 1,377,
1,072, 965, 800 cm-1 1H NMR (300 MHz, CDCl3):
;
d = -2.82 (s, 2H, internal NH), 4.01 (d, J = 15.9 Hz,
1H, SCH2CO), 4.11(d, J = 15.9 Hz, 1H, SCH2CO), 6.27
(s, 1H, CH), 7.34 (d, J = 8.1 Hz, 2H, meso-ArH), 7.49 (d,
J = 8.4 Hz, 2H, ArH), 7.56 (d, J = 8.4 Hz, 2H, ArH),
7.78–7.72 (m, 9H, meso-ArH), 8.09 (d, J = 8.1 Hz, 2H,
meso-ArH), 8.21–8.19 (m, 6H, meso-ArH), 8.65 (d,
J = 4.8 Hz, 2H, b-pyrrolic H), 8.83 (d, J = 4.8 Hz, 2H,
b-pyrrolic H), 8.84 (s, 4H, b-pyrrolic H) ppm; 13C NMR
(75 MHz, CDCl3): d = 33.57, 64.97, 118.52, 120.28,
120.42, 123.04, 123.21, 126.70, 127.75, 128.72, 131.32,
132.16, 134.53, 134.95, 136.90, 138.45, 140.70, 142.01,
170.97 ppm; HRMS (ESI): [M]? calcd for C53H36BrN5OS
869.1824, found 869.1819.
2-(2-Trifluoromethylphenyl)-3-[4-(10,15,20-triphenylpor-
phyrin-5-yl)phenyl]thiazolidin-4-one
(4c, C54H36F3N5OS)
ꢀ
Yield 79%; IR (KBr): m = 1,698, 1,597, 1,473, 1,347,
2-(4-Chlorophenyl)-3-[4-(10,15,20-triphenylporphyrin-5-
yl)phenyl]thiazolidin-4-one (4f, C53H36ClN5OS)
1
1,312, 1,163, 1,119, 1,035, 965, 800, 730 cm-1; H NMR
ꢀ
(300 MHz, CDCl3): d = -2.83 (s, 2H, internal NH), 4.05
(d, J = 15.9 Hz, 2H, SCH2CO), 4.17 (d, J = 16.2 Hz, 1H,
SCH2CO), 6.87 (s, 1H, CH), 7.51 (dd, J = 7.8, 7.5 Hz, 1H,
ArH), 7.65 (d, J = 8.4 Hz, 2H, meso-ArH), 7.75–7.70 (m,
11H, ArH, meso-ArH), 7.86 (d, J = 7.8 Hz, 1H, ArH),
8.12 (d, J = 8.4 Hz, 2H, meso-ArH), 8.66 (d, J = 4.8 Hz,
2H, b-pyrrolic H), 8.27–8.17 (m, 6H, meso-ArH), 8.80 (d,
J = 4.8 Hz, 2H, b-pyrrolic H), 8.83 (s, 4H, b-pyrrolic H)
ppm; 13C NMR (100 MHz, CDCl3): d = 33.21, 60.59,
118.60, 120.19, 120.43, 121.85, 126.67, 127.49, 127.73,
128.82, 132.90, 134.51, 134.99, 137.05, 139.15, 140.65,
142.06, 171.46 ppm; HRMS (ESI): [M ? H]? calcd for
C54H37F3N5OS 860.2671, found 860.2680.
Yield 86%; IR (Nujol): m = 1,677, 1,597, 1,463, 1,377,
1
966, 800 cm-1; H NMR (300 MHz, CDCl3): d = -2.82
(s, 2H, internal NH), 4.03 (d, J = 15.6 Hz, 1H, SCH2CO),
4.13 (d, J = 15.3 Hz, 1H, SCH2CO), 6.34 (s, 1H, CH),
7.43 (s, 4H, ArH), 7.52 (d, J = 8.1 Hz, 2H, meso-ArH),
7.80–7.74 (m, 9H, meso-ArH), 8.10 (d, J = 7.8 Hz, 2H,
meso-ArH), 8.20 (d, J = 7.2 Hz, 6H, meso-ArH), 8.65 (d,
J = 4.8 Hz, 2H, b-pyrrolic H), 8.82 (d, J = 4.8 Hz, 2H,
b-pyrrolic H), 8.83 (s, 4H, b-pyrrolic H) ppm; 13C NMR
(100 MHz, CDCl3): d = 33.63, 65.07, 118.47, 120.30,
120.45, 123.31, 126.68, 127.74, 128.50, 129.36, 131.05,
134.52, 134.99, 137.00, 137.96, 140.74, 142.01, 171.01
ppm; HRMS (ESI): [M]? calcd for C53H36ClN5OS
825.2329, found 825.2335.
2-(4-Trifluoromethylphenyl)-3[4-(10,15,20-triphenylpor-
phyrin-5-yl)phenyl]thiazolidin-4-one
(4d, C54H36F3N5OS)
2-(4-Fluorophenyl)-3-[4-(10,15,20-triphenylporphyrin-5-
yl)phenyl]thiazolidin-4-one (4g, C53H36FN5OS)
ꢀ
ꢀ
Yield 82%; IR (film): m = 1,699, 1,508, 1,473, 1,324,
Yield 96%; IR (Nujol): m = 1,690, 1,599, 1,506, 1,466,
1,167, 1,129, 1,067, 966, 801, 732 cm-1
;
1H NMR
1,377, 1,231, 1,176, 965, 802, 733 cm-1 1H NMR
;
123