V. Cîrcu et al. / Polyhedron 28 (2009) 3739–3746
3745
7.75 (dt, 1H, J = 0.8, 7.5 Hz, H-3); 7.90 (ddd, 1H, J = 1.6, 7.4, 7.5 Hz,
H-4); 8.19–8.21 (m, 2H, ortho-Ph-BTU); 9.28 (ddd, 1H, J = 0.8, 1.6,
5.0 Hz, H-6).
1H NMR (300 MHz, CDCl3) d: 7.02–7.05 (m, 2H, H-40, H-50); 7.29
(ddd, 1H, J = 1.4, 6.0, 7.1 Hz, H-5); 7.33–7.56 (m, 12H, H-30, H-60,
8H-BTU); 7.71 (m, 1H, H-3); 7.86 (m, 1H, H-4); 8.15–8.17 (m, 2H,
ortho-Ph-BTU); 9.18 (dd, 1H, J = 0.8, 6.0 Hz, H-6).
13C NMR (75 MHz, CDCl3) d: 168.9 (C@S), 165.8 (C@O), 145.1
(C-2, ppy), 138.4 (C-4, ppy), 132.7 (C-30, ppy), 131.3 (Ph-BTU),
130.0 (C-40, ppy), 129.4 (Ph-BTU), 128.5 (Ph-BTU), 124.0 (C-60,
ppy), 123.7 (C-50, ppy), 122.2 (C-5, ppy), 119.0 (C-3, ppy), 54.8,
53.7, 21.6, 21.0 (CH2), 11.9 (CH3).
IR (KBr, cmꢀ1): (
1518s, 1501s, 1485s, 1427vs, 752m.
mN–H), 3054w, (mC@N, mC@C), 1636m, 1608m,
Compound 8. Yield 72%, yellow crystals, m.p. 228 °C dec. Anal.
Calc. for C26H21N3OPtS: C, 50.5; H, 3.4; N, 6.8. Found: C, 50.3; H,
3.7; N, 6.5%.
IR (KBr, cmꢀ1): (
1635m, 1606m, 1514s, 1482s, 1423vs, 746m.
mC–H), 2950w, 2930w, 2870w, (mC@N, mC@C),
1H NMR (300 MHz, CDCl3) d: 2.38 (s, 1H, p-CH3); 7.07–7.10 (m,
H-40, H-50); 7.21 (d, 2H, J = 8.6 Hz, 2H-BTU); 7.35 (ddd, 1H, J = 1.6,
6.0, 7.4 Hz, H-5); 7.41–7.58 (m, 7H, H-30, H-60, 5H-BTU); 7.75–
7.77 (m, 1H, H-3); 7.88–7.93 (m, 1H, H-4); 8.20–8.23 (m, 2H,
ortho-Ph-BTU); 9.23 (dd, 1H, J = 1.6, 6.0 Hz, H-6).
Compound 4. Yield 70%, yellow crystals, m.p. 143 °C. Anal. Calc.
for C27H32N3OPtS: C, 51.8; H, 5.2; N, 6.7. Found: C, 51.9; H, 5.5; N,
6.4%.
1H NMR (300 MHz, CDCl3) d: 0.98, 1.05 (2t, 6H, J = 7.3 Hz, 2CH3);
1.35–1.55 (m, 4H, 2CH2); 1.65–1.95 (m, 4H, 2CH2); 3.80–3.93 (m,
4H, 2CH2N); 7.10 (m, 2H, H-40, H-50); 7.32 (ddd, 1H, J = 1.4, 5.0,
7.4 Hz, H-5); 7.40–7.45 (m, 2H, meta-Ph-BTU); 7.48–7.53 (m, 3H,
H-30, H-60, para-Ph-BTU); 7.75 (dt, 1H, J = 0.8, 7.5 Hz, H-3); 7.90
(ddd, 1H, J = 1.6, 7.4, 7.5 Hz, H-4); 8.20–8.22 (m, 2H, ortho-Ph-
BTU); 9.29 (ddd, 1H, J = 0.8, 1.6, 5.0 Hz, H-6).
IR (KBr, cmꢀ1): (
1518s, 1485s, 1431vs, 754m.
mN–H), 3051w, (mC@N, mC@C), 1636m, 1608m,
9. Yield 83%, yellow crystals, m.p. 150 °C. Anal. Calc. for
C26H21N3OPtS: C, 50.5; H, 3.4; N, 6.8. Found: C, 50.2; H, 3.6; N, 6.5%.
1H NMR (300 MHz, CDCl3) d: 2.40 (s, 1H, m-CH3); 7.01–7.03 (m,
2H, H-40, H-50); 7.23–7.52 (m, 10H, H-5, H-30, H60, 7H-BTU); 7.69 -
7.71 (m, 1H, H-3); 7.82–7.88 (m, 1H, H-4); 8.15–8.18 (m, 2H, ortho-
Ph-BTU); 9.17 (dd, 1H, J = 1.6, 6.0 Hz, H-6).
13C NMR (75 MHz, CDCl3) d: 168.9 (C@S), 165.8 (C@O), 145.2
(C-2, ppy), 138.4 (C-4, ppy), 132.8 (C-30, ppy), 131.3 (Ph-BTU),
130.0 (C-40, ppy), 129.4 (Ph-BTU), 128.5 (Ph-BTU), 124.0 (C-60,
ppy), 123.7 (C-50, ppy), 122.2 (C-5, ppy), 119.0 (C-3, ppy), 52.8,
51.8, 30.4, 29.7, 20.7 (CH2), 14.3 (CH3).
IR (KBr, cmꢀ1): (
1512s, 1485s, 1431vs, 751m.
mN–H), 3047w, (mC@N, mC@C), 1636m, 1607m,
Compound 10. Yield 82%, yellow crystals, m.p. 229 °C dec. Anal.
Calc. for C25H18FN3OPtS: C, 48.2; H, 2.9; N, 6.7. Found: C, 47.9; H,
3.3; N, 6.4%.
IR (KBr, cmꢀ1): (
1634m, 1607m, 1518s, 1494s, 1484s, 1418vs, 745m.
mC–H), 2957m, 2930m, 2870w, (mC@N, mC@C),
Compound 5. Yield 80%, yellow crystals, m.p. 79 °C. Anal. Calc.
for C31H40N3OPtS: C, 53.4; H, 5.8; N, 6.0. Found: C, 53.1; H, 6.0;
N, 5.7%.
1H NMR (300 MHz, CDCl3) d: 7.00–7.08 (m, 4H, H-40, H-50, 2H-
BTU); 7.19–7.52 (m, 8H, H-5, H-30, H-60, 5H-BTU); 7.69–7.72 (m,
1H, H-3); 7.82–7.85 (m, 1H, H-4); 8.10–8.13 (m, 2H, ortho-Ph-
BTU); 9.16 (dd, 1H, J = 1.6, 6.0 Hz, H-6).
1H NMR (300 MHz, CDCl3) d: 0.86, 0.94 (2t, 6H, J = 7.1 Hz, 2CH3);
1.21–1.56 (m, 8H, 4CH2); 1.60–1.78 (m, 4H, 2CH2); 1.80–1.99 (m,
4H, 2CH2); 3.77–3.87 (m, 4H, 2CH2N); 7.06–7.11 (m, 2H, H-40, H-
50); 7.32 (ddd, 1H, J = 1.4, 5.0, 7.4 Hz, H-5); 7.41–7.46 (m, 2H,
meta-Ph-BTU); 7.49–7.52 (m, 3H, H-30, H-60, para-Ph-BTU); 7.73
(dt, 1H, J = 0.8, 7.5 Hz, H-3); 7.88 (ddd, 1H, J = 1.6, 7.4, 7.5 Hz, H-
4); 8.18–8.21 (m, 2H, ortho-Ph-BTU); 9.28 (ddd, 1H, J = 0.8, 1.6,
5.0 Hz, H-6).
IR (KBr, cmꢀ1): (
1522s, 1508s, 1485s, 1431vs, 755m.
mN–H), 3077w, (mC@N, mC@C), 1637m, 1607m,
Compound 11. Yield 85%, yellow crystals, m.p. 232 °C. Anal. Calc.
for C25H18ClN3OPtS: C, 47.0; H, 2.8; N, 6.6. Found: C, 46.8; H, 3.1; N,
6.4%.
1H NMR (300 MHz, CDCl3) d: 7.01–7.08 (m, 4H, H-40, H-50, 2H-
BTU); 7.29–7.54 (m, 8H, H-5, H-30, H-60, 5H-BTU); 7.70–7.72 (m,
1H, H-3); 7.83–7.89 (m, 1H, H-4); 8.11–8.14 (m, 2H, ortho-Ph-
BTU); 9.15 (dd, 1H, J = 1.6, 6.0 Hz, H-6).
13C NMR (75 MHz, CDCl3) d: 168.9 (C@S), 165.8 (C@O), 145.1
(C-2, ppy), 138.4 (C-4, ppy), 132.8 (C-30, ppy), 131.3 (Ph-BTU),
130.0 (C-40, ppy), 129.4 (Ph-BTU), 128.4 (Ph-BTU), 124.0 (C-60,
ppy), 123.7 (C-50, ppy), 122.2 (C-5, ppy), 119.0 (C-3, ppy), 52.8,
53.1, 52.1, 31.9, 28.2, 27.4, 27.2, 23.0 (CH2), 14.4 (CH3).
IR (KBr, cmꢀ1): (
1519s, 1485s, 1431vs, 754m.
mN–H), 3052w, (mC@N, mC@C), 1635m, 1607m,
Compound 12. Yield 80%, yellow crystals, m.p. 239 °C. Anal. Calc.
for C25H18BrN3OPtS: C, 43.9; H, 2.7; N, 6.1. Found: C, 43.7; H, 3.0; N,
5.9%.
IR (KBr, cmꢀ1): (
1606m, 1514s, 1482s, 1419vs, 747m.
mC–H), 2925m, 2857m, (mC@N, mC@C), 1635m,
Compound 6. Yield 75%, yellow crystals, m.p. 71 °C. Anal. Calc.
for C35H48N3OPtS: C, 55.8; H, 6.4; N, 5.6. Found: C, 55.5; H, 6.8;
N, 5.4%.
1H NMR (300 MHz, CDCl3) d: 7.08–7.11 (m, 4H, H-40, H-50, 2H-
BTU); 7.35–7.60 (m, 8H, H-5, H-30, H-60, 5H-BTU); 7.76–7.79 (m,
1H, H-3); 7.89–7.95 (m, 1H, H-4); 8.18–8.21 (m, 2H, ortho-Ph-
BTU); 9.22 (dd, 1H, J = 1.6, 6.0 Hz, H-6).
1H NMR (300 MHz, CDCl3) d: 0.86, 0.90 (2t, 6H, J = 7.1 Hz, 2CH3);
1.25–1.44 (m, 16H, 8CH2); 1.63–178 (m, 4H, 2CH2); 1.80–1.98 (m,
4H, 2CH2); 3.78–3.89 (m, 4H, 2CH2N); 7.08–7.11 (m, 2H, H-40,
H-50); 7.30 (ddd, 1H, J = 1.4, 5.0, 7.4 Hz, H-5); 7.40–7.45 (m, 2H,
meta-Ph-BTU); 7.49–7.54 (m, 3H, H-30, H-60, para-Ph-BTU); 7.75
(dt, 1H, J = 0.8, 7.5 Hz, H-3); 7.89 (ddd, 1H, J = 1.6, 7.4, 7.5 Hz, H-4);
8.20–8.22 (m, 2H, ortho-Ph-BTU); 9.29 (ddd, 1H, J = 0.8, 1.6, 5.0 Hz,
H-6).
IR (KBr, cmꢀ1): (
1517s, 1485s, 1431vs, 754m.
mN–H), 3053w, (mC@N, mC@C), 1635m, 1608m,
Compound 13. Yield 77%, yellow crystals, m.p. 220 °C. Anal. Calc.
for C26H21N3O2PtS: C, 49.2; H, 3.3; N, 6.6. Found: C, 48.9; H, 3.6; N,
6.4%.
1H NMR (300 MHz, CDCl3) d: 3.85 (s, 1H, OCH3); 6.94 (d, 2H,
J = 8.0 Hz, BTU); 7.05–7.07 (m, 2H, H-40, H-50); 7.21–7.57 (m, 6H,
H-5, H-30, H-60, 3H-BTU); 7.75–7.77 (m, 1H, H-3); 7.87–7.93 (m,
1H, H-4); 8.11–8.20 (m, 4H, BTU); 9.24 (dd, 1H, J = 1.6, 6.0 Hz, H-6).
13C NMR (75 MHz, CDCl3) d: 168.3 (C@O), 165.5 (C@S), 144.9
(C-2, ppy), 138.0 (C-4, ppy), 132.4 (C-30, ppy), 130.9 (Ph-BTU),
129.6 (C-40, ppy), 129.1 (Ph-BTU), 128.1 (Ph-BTU), 123.6 (C-60,
ppy), 123.4 (C-50, ppy), 121.8 (C-5, ppy), 118.6 (C-3, ppy), 52.8,
51.7, 31.8, 29.3, 27.9, 27.2, 22.6 (CH2), 14.1 (CH3).
IR (KBr, cmꢀ1): (
mN–H), 3044w, (mC@N, mC@C), 1636m, 1607m,
1509s, 1484s, 1435vs, 751m.
IR (KBr, cmꢀ1): (
1636m, 1607m, 1517s, 1497s, 1483s, 1420vs, 742m.
mC–H), 2950m, 2925m, 2870m, (mC@N, mC@C),
Acknowledgements
Compound 7. Yield 77%, yellow crystals, m.p. 220 °C. Anal. Calc.
for C25H19N3OPtS: C, 49.7; H, 3.2; N, 7.0. Found: C, 49.5; H, 3.6; N,
6.8%.
The authors wish to thank MECI (Romanian Ministry of Educa-
tion and Innovation, Project PNII ID_954) for funding this study