A. Artillo et al. / Journal of Organometallic Chemistry 692 (2007) 1277–1284
1283
DMSO-d6) d = 7.81 (m, 2H), 7.67–7.57 (m, 4H overlapped),
4.41 (m, 2H), 1.79 (m, 2H), 1.00 (t, J = 7.2 Hz, 3H); 13C
NMR (75.5 MHz, DMSO) d = 232.2, 203.5, 198.6, 148.2,
145.6, 132.3, 129.8, 129.2, 128.2, 122.4, 60.6, 21.1, 10.5;
lapped), 7.40 (m, 2H), 7.08 (d, J = 1.5 Hz, 1H), 3.84 (q,
J = 7.1 Hz, 2H), 1.23 (t, J = 7.1 Hz, 3H); 13C NMR
(100.6 MHz, CDCl3) d = 234.2, 203.6, 198.1, 149.3, 148.9,
131.7, 130.9, 129.2, 127.6, 126.6, 42.7, 13.6; IR (CHCl3):
3019, 2061, 1929, 1685, 1560, 1216, 770 cmꢀ1; EI-MS
(70 eV) 184W m/z: 524 (M+), 496 (M+ ꢀ CO), 440
(M+ ꢀ 3CO), 412 (M+ ꢀ 4CO).
IR (KBr): 2962, 2361, 1898, 1689, 1573, 1026, 802 cmꢀ1
;
EI-MS (70 eV) 184W m/z: 538 (M+), 510, 480, 452, 424.
4.11. Compound 4i
4.16. Compound 5h
1
Dark red solid; m.p. 140 °C dec.; H NMR (400 MHz,
CDCl3) d = 12.07 (bs, 1H, NH), 7.92 (bs, 1H), 7.84 (m,
2H), 7.67 (m, 1H), 7.59 (2H), 4.61 (2H), 1.82 (m, 2H),
1.50 (m, 1H), 0.99 (t, J = 7.1 Hz, 3H). 13C NMR
(75.5 MHz, CDCl3) d = 241.2, 203.2, 198.4, 150.1, 141.9,
132.7, 129.6, 127.5, 124.8, 59.8, 30.3, 20.0, 13.8. IR (KBr,
CHCl3): 2962, 2060, 1897, 1666, 1512, 1072 cmꢀ1; ES-MS
184W m/z: 497 [(M + H)+ ꢀ 2CO], 469 [(M + H)+ ꢀ 3CO],
441 [(M + H)+ ꢀ 4CO], 413 [(M + H)+ ꢀ 5CO].
Orange solid; m.p. 158–162 °C; 1H NMR (400 MHz,
CDCl3) d = 11.09 (bs, 1H, NH), 7.63–7.52 (m, 3H over-
lapped), 7.39 (m, 2H), 7.07 (bs, 1H), 3.73 (m, 2H), 1.64
(m, 2H), 0.78 (t, J = 7.4 Hz, 3H). 13C NMR (100.6 MHz,
CDCl3) d = 229.0, 198.1, 192.9, 144.2, 143.3, 126.5, 125.6,
123.9, 122.4, 121.0, 43.4, 24.5, 16.5. IR (KBr): 3433,
2923, 2060, 1905, 1704, 1566, 1458, 1064, 586 cmꢀ1; EI-
MS (70 eV) 184W m/z: 538 (M+), 509, 454, 426.
4.12. Compound 4l
4.17. Compound 5i
1
Red solid; m.p. 176 °C dec.; 1H NMR (400 MHz,
CDCl3) d = 11.05 (bs, 1H, NH), 7.91 (bs, 1H), 7.77 (m,
2H), 7.65 (m, 1H), 7.59 (m, 2H), 6.02 (m, 1H), 5.31 (m,
3H overlapped), 5.20 (d, J = 17.0 Hz, 1H); 13C NMR
(100.6 MHz, CDCl3) d = 243.3, 203.2, 198.2, 149.3, 141.7,
132.9, 131.5, 129.8, 129.6, 127.3, 124.4, 118.0, 61.2; IR
(KBr): 2978, 2060, 1905, 1690, 1574, 1512 cmꢀ1; ES-MS
184W m/z: 559 [(M + Na)+], 508 [(M+ ꢀ CO], 531
[(M + Na)+ ꢀ CO], 447 [(M + Na)+ ꢀ 4CO].
Orange solid; m.p. 178 °C dec.; H NMR (400 MHz,
CDCl3) d = 11.2 (bs, 1H, NH), 7.62–7.53 (m, 3H over-
lapped), 7.40 (m, 2H), 7.07 (d, J = 1.4 Hz, 1H), 3.77 (m,
2H), 1.60 (m, 2H), 1.16 (m, 2H), 0.78 (t, J = 7.1 Hz, 3H);
13C NMR (75.5 MHz, CDCl3) d = 234.1, 203.4, 198.1,
149.4, 148.7, 131.7, 130.8, 129.1, 127.7, 126.3, 47.0, 30.2,
19.7, 13.2; IR (KBr): 2962, 2360, 1905, 1697, 1566, 1458,
1072 cmꢀ1; EI-MS (70 eV) 184W m/z: 552 (M+), 524
(M+ ꢀ CO), 468 (M+ ꢀ 3CO), 440 (M+ ꢀ 4CO), 412
(M+ ꢀ 5CO).
4.13. Compound 4m
4.18. Compound 5l
Red solid; m.p. 154–155 °C; 1H NMR (400 MHz,
CDCl3) d = 11.70 (bs, 1H, NH), 7.96 (s, 1H), 7.67 (m,
3H overlapped), 7.49 (2H), 7.30 (m, 3H overlapped), 7.16
(bd, J = 7.2 Hz, 2H), 5.89 (bs, 2H); 13C NMR
(100.6 MHz, CDCl3) d = 243.4, 202.9, 197.9, 149.8, 142.1,
135.3, 132.6, 129.6, 129.3, 128.5, 127.6, 127.3, 126.0,
1
Orange solid; m.p. 179 °C dec.; H NMR (400 MHz,
CDCl3) d = 11.50 (bs, 1H, NH), 7.59 (m, 1H), 7.53 (m,
2H), 7.41 (m, 2H), 7.10 (bd, J = 1.4 Hz, 1H), 5.82 (1H,
ddt, J = 17.0, 10.2, 5.6 Hz), 5.26 (1H, bd, J = 10.2 Hz),
5.01 (bd, J = 17.0 Hz, 1H), 4.37 (bd, J = 5.6 Hz, 2H); 13C
NMR (100.6 MHz, CDCl3) d = 235.2, 203.5, 198.0, 149.1,
148.8, 131.3, 130.9, 130.4, 128.9, 127.8, 126.5, 119.4, 49.3;
IR (KBr): 2924, 2060, 1905, 1705, 1566, 1458 cmꢀ1; ES-
MS 184W m/z: 537 [(M + H)+], 509 [(M + H)+ ꢀ CO],
481 [(M + H)+ ꢀ 2CO], 453 [(M + H)+ ꢀ 3CO], 425
[(M + H)+ ꢀ 4CO].
124.3, 62.5; IR (KBr): 2924, 2060, 1921, 1682, 1512 cmꢀ1
;
EI-MS (70 eV) 184W m/z: 586 (M+), 558, 502, 474.
4.14. Compound 5f
Red orange solid; m.p. 180 °C dec.; 1H NMR
(400 MHz, CDCl3) d = 11.46 (bs, 1H, NH), 7.65–7.53 (m,
3H overlapped), 7.42 (m, 2H), 7.14 (d, J = 1.4 Hz, 1H),
3.36 (s, 3H); 13C NMR (100.6 MHz, CDCl3) d = 234.4,
203.5, 198.1, 149.4, 149.2, 131.6, 131.2, 129.3, 127.8,
126.1, 34.8; IR (CHCl3): 2926, 2063, 1930, 1692, 1560,
1206, 772 cmꢀ1; EI-MS (70 eV) 184W m/z: 510 (M+), 482
(M+ ꢀ CO), 426 (M+ ꢀ 3CO).
4.19. Compound 5m
1
Solid; m.p. 160–164 °C; H NMR (400 MHz, CDCl3)
d = 10.8 (bs, 1H, NH), 7.55 (m, 1H), 7.45 (m, 2H), 7.29–
7.21 (m, 6H overlapped), 7.10 (m, 1H), 6.92 (m, 2H),
5.04 (bs, 2H); 13C NMR (100.6 MHz, CDCl3) d = 243.6,
203.2, 198.0, 149.2, 148.8, 134.7, 131.5, 130.9, 129.0,
128.8, 128.2, 127.9, 127.3, 126.5, 49.9; IR (KBr): 3464,
2924, 2060, 1929, 1689, 1458 cmꢀ1; EI-MS (70 eV) 184W
m/z: 586 (M+), 558 (M+ ꢀ CO), 502 (M+ ꢀ 3CO), 474
(M+ ꢀ 4CO), 446 (M+ ꢀ 5CO).
4.15. Compound 5g
Yellow solid; m.p. 185 °C dec.; 1H NMR (400 MHz,
CDCl3) d = 11.30 (bs, 1H, NH), 7.62–7.52 (m, 3H over-