1088
H. A. K. Abd El-Aal
C-5), 129.4 (2C, Ar, C-300, C-500), 131.4 (1C, Ar, C-7), 136.5 (1C,
Ar, C-60), 138.8 (2C, Ar, C-4, C-50), 141.6 (1C, Ar, C-400), 148.2
(2C, Ar, C-8a, C-30), 161.1 (1C, Ar, C-40), 166.5 (1C, Ar, C-2),
169.4 (1C, COOH). m/z (EI, 70 eV) (%) 419 (Mþ, 4), 401 (1),
387 (10), 374 (2), 360 (13), 298 (4), 284 (11), 282 (18), 265
(100), 252 (74), 226 (11), 207 (26), 202 (12), 191 (99), 189 (92),
178 (56), 167 (33), 165 (77), 152 (17), 105 (20), 91 (56), 77 (15).
Anal. Calc. for C22H17N3O4S (419): C 63.00, H 4.05, N 10.02,
S 7.63. Found: C 63.14, H 4.10, N 9.89, S 7.52 %.
202 (12), 191 (99), 178 (53), 167 (17), 165 (61), 152 (15), 105
(3), 91 (98), 77 (8). Anal. Calc. for C23H19N3O4S (433):
C 63.74, H 4.38, N 9.69, S 7.39. Found: C 63.68, H 4.43,
N 9.75, S 7.30 %.
2-(2-(N-Benzyl-N-tosylamino)quinolin-3-yl)acetic Acid (3f)
White crystals; 78 %; mp 150–1528C (benzene). vmax (KBr)/cmꢀ1
3095, 2980, 2780, 1720, 1600, 1590, 1480, 1430, 1360, 1130, 760.
dH (90 MHz, CDCl3) 2.4 (s, 3H, CH3), 3.5 (s, 2H, CH2), 4.5 (s, 2H,
CH2), 6.8–8.5 (m, 13H, Ar–H), 10.8 (s, 1H, COOH). dC
(100 MHz, CDCl3) 25.3 (1C, –CH3), 39.8 (1C, –CH2), 48.0 (1C,
N–CH2), 122.0 (1C, Ar, C-6), 121.4 (1C, Ar, C-4a), 121.2 (1C, Ar,
C-3), 125.0 (1C, Ar, C-8), 126.1 (1C, Ar, C-5), 126.8 (1C, Ar,
C-40), 127.2 (4C, Ar, C-20, C-60, C-20, C-60), 127.9 (1C, Ar, C-8),
128.6 (2C, Ar, C-30, C-50), 129.4 (2C, Ar, C-30, C-50), 134.5 (1C,
Ar, C-4), 136.7 (1C, Ar, C-100), 141.6 (2C, Ar, C-10, C-400), 144.8
(1C, Ar, C-8a), 168.7(1C, Ar, C-2), 175.3 (1C, COOH). m/z (EI,
70 eV) (%) 446 (Mþ, 24), 401 (25), 387 (12), 360 (10), 297 (2),
282 (7), 268 (100), 252 (40), 226 (9), 207 (4), 202 (11), 191 (92),
178 (53), 167 (15), 165 (42), 152 (15), 105 (3), 91 (97), 77 (12).
Anal. Calc. for C25H22N2O4S (446): C 67.26, H 4.93, N 6.27, S
7.17. Found: C 67.18, H 4.91, N 6.29, S 7.24 %.
2-(N-Benzyl-N-tosylamino)quinoline-3-Carboxylic
Acid (3c)
White crystals; 82%; mp 140–1428C (ethanol). vmax (KBr)/cmꢀ1
3065, 2973, 2550, 1690, 1610, 1570, 1465, 1440, 1335, 1250,
760. dH (90 MHz, CDCl3) 2.4 (s, 3H, CH3), 4.5 (s, 2H, CH2), 6.7–
8.3 (m, 14H, Ar–H), 10.8 (s, 1H, COOH). dC (100 MHz, CDCl3)
25.4 (1C, –CH3), 47.7 (1C, N–CH2), 110.8 (1C, Ar, C-3), 120.2
(1C, Ar, C-4a), 123.1 (1C, Ar, C-6), 125.2 (1C, Ar, C-8), 126.8
(1C, Ar, C-40), 127.2 (4C, Ar, C-20, C-60, C-200, C-600), 128.6 (3C,
Ar, C-5, C-30, C-50), 129.4 (2C, Ar, C-300, C-500), 131.6 (1C, Ar,
C-7), 136.7 (1C, Ar, C-100), 138.3 (1C, Ar, C-4), 141.6 (2C, Ar,
C-10, C-400), 148.3 (1C, Ar, C-8a), 167.2 (1C, Ar, C-2), 169.4 (1C,
COOH). m/z (EI, 70 eV) (%) 432 (Mþ, 17), 387 (6), 360 (14), 298
(2), 286 (2), 282 (8), 268 (100), 265 (50), 252 (43), 227 (6), 215
(7), 207 (7), 202 (10), 191 (95), 189 (67), 179 (21), 165 (54), 152
(13), 105 (5), 91 (97), 77 (9). Anal. Calc. for C24H20N2O4S (432):
C 66.66, H 4.62, N 6.48, S 7.40. Found: C 66.74, H 4.68, N 6.37, S
7.52%.
3-(2-(N-Phenyl-N-tosylamino)quinolin-3-yl)propanoic
Acid (3g)
White crystals; 85%; mp 155–1578C (ethanol). vmax (KBr)/cmꢀ1
3060, 2979, 2520, 1725, 1605, 1585, 1475, 1435, 1365, 1280,
1083, 765. dH (90 MHz, CDCl3) 2.3 (t, 2H, 6, CH2), 2.5 (s, 3H,
CH3), 2.8 (t, 2H, 6, CH2), 6.7–8.3 (m, 14H, Ar–H), 11.2 (s, 1H,
COOH). dC (100MHz, CDCl3) 25.4 (1C, –CH3), 25.1 (1C,
–CH2), 36.4 (1C, –CH2–COOH), 116.3 (2C, Ar, C-20, C-60),
118.8 (1C, Ar, C-40), 121.2 (2C, Ar, C-3, C-4a), 122.0 (1C, Ar,
C-6), 125.0 (1C, Ar, C-8), 126.1 (1C, Ar, C-5), 127.2 (2C, Ar,
C-200, C-600), 127.9 (1C, Ar, C-7), 129.6 (4C, Ar, C-30, C-50, C-30,
C-50), 134.5 (1C, Ar, C-4), 136.7 (1C, Ar, C-100), 141.6 (1C, Ar,
C-400), 144.8 (1C, Ar, C-8a), 146.7 (1C, Ar, C-10), 168.7 (1C,
Ar, C-2), 177.6 (1C, COOH). m/z (EI, 70 eV) (%) 446 (Mþ, 12),
386 (18), 360 (12), 297 (8), 282 (13), 269 (100), 252 (62), 226
(9), 207 (12), 202 (10), 191 (97), 178 (56), 167 (18), 165 (52),
152 (15), 105 (4), 91 (92), 77 (7). Anal. Calc. for C25H22N2O4S
(446): C 67.26, H 4.93, N 6.27, S 7.17. Found: C 67.25, H 5.07,
N 6.15, S 7.20 %.
2-(2-(N-Phenyl-N-tosylamino)quinolin-3-yl)acetic Acid (3d)
White needles; 77%; mp 164–1668C (ethanol). vmax (KBr)/cmꢀ1
3065, 2975, 2568, 1715, 1590, 1575, 1450, 1430, 1380, 1130,
765. dH (90 MHz, CDCl3) 2.4 (s, 3H, CH3), 3.5 (s, 2H, CH2), 6.3–
8.2 (m, 14H, Ar–H), 11.5 (s, 1H, COOH). dC (100 MHz, CDCl3)
25.5 (1C, –CH3), 39.8 (1C, –CH2), 116.3 (2C, Ar, C-20, C-60),
118.8 (1C, Ar, C-40), 121.4 (2C, Ar, C-3, C-4a), 122.0 (1C, Ar,
C-6), 125.0 (1C, Ar, C-8), 126.1 (1C, Ar, C-5), 127.2 (2C, Ar,
C-200, C-600), 127.9 (1C, Ar, C-7), 129.4 (4C, Ar, C-30, C-50, C-30,
C-50), 134.5 (1C, Ar, C-4), 136.7 (1C, Ar, C-100), 141.6 (1C, Ar,
C-400), 144.8 (1C, Ar, C-8a), 146.7 (1C, Ar, C-10), 168.7 (1C, Ar,
C-2), 175.3 (1C, COOH). m/z (EI, 70 eV) (%), 432 (Mþ, 22), 387
(5), 360 (13), 345 (2), 297 (2), 282 (7), 268 (100), 253 (38), 226
(8), 207 (4), 202 (11), 191 (97), 178 (50), 167 (18), 165 (58), 152
(14), 105 (4), 91 (96), 77 (8). Anal. Calc. for C24H20N2O4S (432):
C 66.66, H 4.62, N 6.48, S 7.40. Found: C 66.64;H 4.60; N 6.54; S
7.37%.
3-(2-(N-(Pyridin-2-yl)-N-tosylamino)quinolin-3-yl)
propanoic Acid (3h)
White crystals; 80%; mp 152–1548C (ethanol). vmax (KBr)/cmꢀ1
3035, 2965, 2610, 1724, 1600, 1575, 1450, 1430, 1375, 1035,
759. dH (90 MHz, CDCl3) 2.3 (s, 3H, CH3), 2.5 (t, 2H, 7.5, CH2),
2.9 (t, 2H, 7.5, CH2), 6.7–8.2 (m, 13H, Ar–H), 10.8 (s, 1H,
COOH). dC (100MHz, CDCl3) 25.1 (1C, –CH3), 27.3 (1C,
–CH2), 36.4 (1C, –CH2–COOH), 109.9 (1C, Ar, C-60), 113.3 (1C,
Ar, C-40), 121.2 (2C, Ar, C-3, C-4a), 122.0 (1C, Ar, C-6), 125.0
(1C, Ar, C-8), 126.1 (1C, Ar, C-5), 127.2 (2C, Ar, C-200, C-600),
127.9 (1C, Ar, C-7), 129.4 (2C, Ar, C-300, C-500), 134.5 (1C, Ar,
C-4), 136.7 (1C, Ar, C-10), 138.3 (1C, Ar, C-50), 141.6 (1C, Ar,
C-400), 144.8 (1C, Ar, C-8a), 148.2 (1C, Ar, C-30), 161.1 (1C, Ar,
C-10), 168.7 (1C, Ar, C-2), 177.5 (1C, COOH). m/z (EI, 70 eV)
(%) 447 (Mþ, 32), 402 (8), 387 (9), 362 (11), 297 (8), 282 (10),
268 (100), 253 (60), 225 (11), 207 (10), 205 (15), 191 (98), 178
(62), 167 (20), 152 (10), 91 (90), 77 (6). Anal. Calc. for
C24H21N3O4S (447): C 64.42, H 4.69, N 9.39, S 7.15. Found:
C 64.59, H 4.64, N 9.25, S 7.22 %.
2-(2-(N-(Pyridin-2-yl)-N-tosylamino)quinolin-3-yl)acetic
Acid (3e)
Yellowish crystals; 75 %; mp 146–1488C (acetone). vmax (KBr)/
cmꢀ1 3110, 2978, 2765, 1715, 1600, 1590, 1460, 1430, 1330,
1120, 765. dH (90 MHz, [D6]DMSO) 2.4 (s, 3H, CH3), 3.5 (s,
2H, CH2), 6.7–8.2 (m, 13H, Ar–H), 11.4 (s, 1H, COOH). dC
(100 MHz, CDCl3) 25.2 (1C, –CH3), 39.8 (1C, –CH2), 109.9
(1C, Ar, C-60), 113.3 (1C, Ar, C-40), 121.4 (2C, Ar, C-3, C-4a),
122.0 (1C, Ar, C-6), 125.0 (1C, Ar, C-8), 126.1 (1C, Ar, C-5),
127.2 (2C, Ar, C-200, C-600), 127.9 (1C, Ar, C-7), 129.4 (2C, Ar,
C-300, C-500), 134.5 (1C, Ar, C-4), 136.7 (1C, Ar, C-10), 138.3
(1C, Ar, C-50), 141.6 (1C, Ar, C-400), 144.8 (1C, Ar, C-8a), 148.2
(1C, Ar, C-30), 161.1 (1C, Ar, C-10), 168.7 (1C, Ar, C-2), 176.3
(1C, COOH). m/z (EI, 70 eV) (%) 433 (Mþ, 14), 387 (5), 360
(12), 297 (2), 282 (7), 269 (100), 252 (47), 226 (9), 207 (4),