Med Chem Res (2015) 24:1635–1643
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Synthesis of tributyltannic[3-(30,40-dichlorophenylami-
do)propanoate] (1) white crystals (chloroform methanol, 4:
1 v/v) Complex 1 was synthesized by refluxing equimolar
amount of ligand HL (1 g, 3.80 mmol), Bu3SnCl (1.25 g,
3.80 mmol), and triethylamin (0.53 mL, 3.80 mmol) in dry
toluene (100 mL). The filtrate was concentrated to dryness
under reduced pressure, and the product was Purified by
recrystallization from a chloroform methanol (4:1 v/v)
mixture at room temperature. M.p. 66–68 °C. IR
(4000–200 cm-1, KBr): 3327 m (NH), 1705 m (amide C=O),
1548 m (COasym), 1406 m (COsym), 142 (Dm), 520 m (Sn–
Synthesis of tributylstannic(20,40,60-trichlorobenzoate) (4)
white needles (chloroform methanol, 4:1 v/v) Complex 4
was synthesized in the same way as 1, by refluxing equi-
molar amount of 20,40,60-trichlorobenzoic acid (1 g, 4.4
mmol), Bu3SnCl (1.3 g, 4.4 mmol), and triethylamin (0.
62 mL, 4.4 mmol) in dry toluene (100 mL). The filtrate
was concentrated to dryness under reduced pressure, and
the product was purified by recrystallization from a chlo-
roform methanol (4:1 v/v) mixture at room temperature. M.
p. 79–80 °C. IR (4000–200 cm-1, KBr): 1547 m (COasym),
1417 m (COsym), 130 (Dm), 552 m (Sn–C), 465 m (Sn–O). 1H
NMR (CDCl3, 300 MHz) d (ppm): 7.79 (s, 2H 3/5); 0.81 (t,
1
C), 416 m (Sn–O). H NMR (CDCl3, 300 MHz) d (ppm):
1
1
7.70 (s, 1H, 2); 7.53 (d, J (1H, H) = 7.6 Hz, 1H 5); 7.69
J (1H, H) = 6.9 terminal methyl protons of butyl); 1.0–1.
1
1
(d, J (1H, H) = 7.6 Hz, 1H, 6); 2.57 (t, J (1H, H) = 6.0
Hz, 2H, 8); 2.69 (t, J (1H, 1H) = 6.0 Hz, 2H 9); 8.5 (s, 1H
NH); 0.889 (t, 7.2 terminal methyl protons of butyl);
1.23–1.37 (m, 6H of first 3 carbons of butyl). 13C NMR
(CDCl3-d3, 75 MHz) d (ppm): 137.5 (C1); 121.5 (C2); 132
(C3); 126 (C4); 130.2 (C5); 119.5 (C6); 170.9 (C7); 30.3
(C8); 29.7 (C9); 178 (C10); (29.71 J [349,332], 27.92J [21],
26.83J [64], 14.4, n-butyl carbons). EI-MS, m/z (%):
[C14H13N2O6Cl2Sn]? 496 (100), [C6H4Cl2Sn]? 269
(12), [C7H3ClSn]? 242 (20), [SnCOO]? 164 (18), [SnL]
341 (8), [R3Sn]? 291 (8), [R2Sn]? 234 (5), [RSn]? 177
(30), [Sn]? 120 (7), [C6H4NCl2]? 161 (19), [C4H9]? 57
(25). Anal. Calcd for C22H35NO4Cl2Sn (566.82): C 46.61;
H 6.17; N 2.47; Found: C (47.63); H (6.53); N (2.54).
51 (m, 6H of first 3 carbons of butyl). 13C NMR (CDCl3-
d3, 75 MHz) d (ppm): 131.7 (C1); 135.6 (C2/6); 129.3 (C3/
1
2
5); 135.3 (C4); 170.8 (C7); (28.1 J [355], 27.8 J [21],
26.1 3J [60], 14.0, n-butyl carbons). EI-MS, m/z (%):
[R2SnCOOL] 459 (82), [SnCOOL]? 345 (12), [SnL] 301
(44), [R2Sn]? 234 (12), [RSn]? 177 (32), [Sn]? 120 (33),
[C7H2OCl3]? 208 (18), [C4H9]? 57 (100). Anal. Calcd for
C19H29O2Cl3Sn (514.24): C 44.37; H 5.64; Found: C (44.
41); H (5.71).
Synthesis of trimethylstannic[3-(2-fluorophenylamido)pro-
panoate] (7) white crystals (chloroform methanol, 4:1
v/v) Complex 7 was synthesized in the same way as 1, by
refluxing equimolar amount of ligand HL (1 g, 4.74
mmol), Me3SnCl (0.94 g, 4.74 mmol), and triethylamin (0.
65 mL, 4.74 mmol) in dry toluene (100 mL). The filtrate
was concentrated to dryness under reduced pressure, and
the product was purified by recrystallization from a chlo-
roform methanol (4:1 v/v) mixture at room temperature. M.
p. 158–161 °C. IR (4000–200 cm-1, KBr): 3385 m (NH),
1699 m (amide C=O), 1578 m (COasym), 1419 m (COsym),
Synthesis of tributylstannic[3-(3,5-dimethylphenylami-
do)propionate] (2) white crystals (chloroform methanol, 4:
1 v/v) Complex 2 was synthesized in the same way as 1,
by refluxing equimolar amount of ligand HL (1 g, 4.6
mmol), Bu3SnCl (1.48 g, 4.6 mmol), and triethylamin
(0.64 mL, 4.6 mmol) in dry toluene (100 mL). The filtrate
was concentrated to dryness under reduced pressure, and
the product was purified by recrystallization from a chlo-
roform methanol (4:1 v/v) mixture at room temperature. M.
p. 152–154 °C. IR (4000–200 cm-1, KBr): 3300 m (NH),
1713 m (amide C=O), 1556 m (COasym), 1412 m (COsym),
1
156 (Dm), 530 m (Sn–C), 462 m (Sn–O). H NMR (CDCl3,
300 MHz) d (ppm): 7.20–7.10 (m, 4H, 3–6); 2.68 (t, J (1H,
1H) = 9.0 Hz, 2H, 8); 2.75 (t, J (1H, 1H) = 9.0 Hz, 2H, 9);
2
1
9.48 (s, 1H NH); 0.084 (s, 9H methyl); J [119/117Sn, H]
52, 58.8 Hz. 13C NMR (CDCl3-d3, 75 MHz) d (ppm): 123.
2 (C1); 154.8 (C2) 1J [13C–19F] 243 Hz; 114.8 (C3)
2J [13C–19F] 18.75 Hz; 124.67 (C4) 3J [13C–19F] 11.25 Hz;
127.2 (C5); 127 (C6); 170.8 (C7); 30.6 (C8); 33.5 (C9);
175.1 (C10); -2.3 (1J [378] methyl carbons).EI-MS, m/z
(%): [R2SnCOOL] 360 (78), [C8H10NOFSn]? 270 (30),
[C5H4O2Sn]? 193 (52), [R3Sn]? 165 (100), [RSn]? 135
(36), [C6H5NF]? 110 (58), [C3H3O]? 55 (22). Anal. Calcd
for C13H18NO4FSn (389.83): C 40.05; H 4.62; N 3.59;
Found: C (40.90); H (4.92); N (3.69).
1
144 (Dm), 535 m (Sn–C), 431 m (Sn–O). H NMR (CDCl3,
300 MHz) d (ppm): 7.70 (s, 1H, 2); 7.53 (s, 1H, 4); 7.69 (d,
1H, 6); 2.57 (d, J(1H, 1H) = 6.0 Hz, 1H, 10); 2.69 (d, J(1H,
1H) = 6.0 Hz, 1H 11); 11.02 (s, 1H NH); 0.85 (t, 7.5 ter-
minal methyl protons of butyl); 1.22–1.34 (m, 6H of first 3
carbons of butyl). 13C NMR (CDCl3-d3, 75 MHz) d (ppm):
133.2 (C1); 124.9 (C2/6); 138.6 (C3/5); 126 (C4); 21 (C7/
8); 163.7 (C9); 139.1 (C10); 132.1 (C11); 168.4 (C12); (29.
51J [342], 27.92J [27], 26.93J [77], 14.0, n-butyl carbons).
EI-MS, m/z (%): [R2SnCOOL] 451 (22), [R3Sn]? 297 (38),
[R2Sn]? 234 (16), [RSn]? 177 (39), [Sn]? 120 (49),
[C12H12NO2]? 202 (78), [C11H12NO]? 174 (37), [C4H9]?
57 (100). Anal. Calcd for C24H39NO4Sn (523.96): C 55.01;
H 7.44; N 2.67; Found: C (53.8); H (7.51); N (2.61).
Synthesis of trimethylstannic(30,40-dimethoxybenzoate) (8)
white crystals (chloroform methanol, 4:1 v/v) Complex 8
was synthesized in the same way as 1, by refluxing equimolar
amount of 30,40-dimethoxybenzoic acid (1 g, 5.5 mmol),
123