7
290
A. Kumar et al. / Tetrahedron Letters 48 (2007) 7287–7290
Compound 6d: kmax (loge) 412 (5.7), 432 (4.34), 535 (3.6).
2
9. Yang, J.; Feng, K.; Li, Y.; Zang, H. M.; Wang, H.;
Chou, C.; Liang, R. U.S. Patent Application
0,050,039,274, 2005.
0. Adler, A. D.; Longo, F. R.; Varadi, V. Inorg. Synth. 1976,
6, 213.
1. Tharsh, T. P.; Wilson, L. J. Inorg. Chem. 2001, 40,
556.
2. George, R. G.; Padmanabhan, M. Polyhedron 2005, 24,
79.
3. Selected spectral data: H and C NMR spectra were
measured in CDCl at 400 MHz and 100 MHz and UV–
visible spectra were recorded in chloroform. Compound
1
Compound 6e: H d 3.38–3.56 (m, 12H, o-OCH
3
), 3.77–
2
3.98 (m, 12H, p-OCH ), 6.68–6.75 (m, 8H, phenyl), 7.14–
3
13
3
3
3
3
7.84 (m, 4H, phenyl), 8.58 (s, 8H, pyrrole); C d 55.5
(o-CH ), 103.3 (meso-C), 142.94 (a-C, pyrrole), 131.56
1
3
(b-C, pyrrole), 160.9; kmax (loge) 418 (5.12), 530 (4.00). IR
À1
4
(KBr pellet, cm ) 2956 (m C–H, OCH ), 1600 (m C@C Bz),
3
1248 (m C–O). C H N (%): Calcd: C, 68.51; H, 4.86; N,
6
6.15. Found: C, 68.47; H, 4.75; N, 6.11.
Compound 6g: H d 3.74–3.80 (m, 12H, o-OCH ), 3.9–
1
13
1
3
3
4.01 (m, 12H, p-OCH
7.81 (m, 4H, phenyl), 8.76 (s, 8H, pyrrole); C d 55.5
(o-OCH ), 55.8 (p-OCH ), 103.15, 116.1, 124.5 (meso-C),
3
), 6.76–6.80 (m, 8H, phenyl), 7.69–
13
2
b: kmax (loge) 425 (6.2), 548 (5.0), 586 (4.1). FAB-MS:
3
3
À1
m/z 817, IR (KBr pellet, cm ): 3062 (m Cp–H), 3062
m C–H Bz), 1577 (m C@C Bz), 1449 (m Cp–Cp), 1446 (m
Cp–N), 1357 (m Cp–Cp), 1182 (d Cp–H), 1089 (d CCN), C
135.86 (b-C, pyrrole), 150.5 (a-C, pyrrole), 105.6, 130.74,
131.3, 160.15, 160.98; kmax (loge) 422 (5.66), 549 (4.36),
589 (4.55). FAB-MS: m/z 856, IR (KBr pellet, cm ): 2945
(
À1
H N (%): Calcd: C, 64.65; H, 2.96; N, 6.85. Found: C,
3
(m C–H, OCH ), 1605 (m C@C Bz), 1248 (m C–O). C H N
(%): Calcd: C, 73.05; H, 5.42; N, 6.55. Found: C, 72.97; H,
5.35; N, 6.39.
64.53; H, 2.88; N, 6.82.
Compound 3b: kmax (loge) 427 (5.54), 552 (4.36), 609
À1
(
4.04). FAB-MS: m/z 744, IR (KBr pellet, cm ) 3510 (m
Compound 7b: kmax (loge) 427 (5.41), 460 (4.52), 548
O–H), 3012 (m Cp–H), 2920 (m C–H Bz), 1589 (m C–C Bz),
(4.25), 660 (3.74). FAB-MS: m/z 921, IR (KBr pellet,
À1
1481 (m Cp–Cp), 1442 (m Cp–N). C H N (%): Calcd: C,
cm ): 2926 (m C–H, OCH ), 1605 (m C@C Bz), 1245 (m C–
3
71.06; H, 3.8; N, 7.53. Found: C, 71.01; H, 3.68; N, 7.49.
O). C H N (%): Calcd: C, 67.90; H, 4.82; N, 6.09. Found:
C, 67.97; H, 4.75; N, 6.01.
Compound 5b: kmax (loge) 429 (5.52), 464 (4.42), 550
À1
(
4.32). FAB-MS: m/z 921, IR (KBr pellet, cm ) 2926 (m
Compound 8b: kmax (loge) 430 (5.78), 508 (3.92), 547
C–H, OCH
3
), 1605 (m C@C Bz), 1505 (m Cp–Cp), 1245 (m
(4.61), 586 (3.90). FAB-MS: m/z 921, IR (KBr pellet,
À1
C@O). C H N (%): Calcd: C, 67.90; H, 4.82; N, 6.09.
Found: C, 67.97; H, 4.75; N, 6.01.
Compound 5d: kmax (loge) 410 (5.7), 432 (4.34), 535 (3.6).
cm ) 2932 (m C–H, OCH
3
), 1582 (m C@C Bz), 1259 (m C–
O). C H N (%): Calcd: C, 67.90; H, 4.82; N, 6.09. Found:
C, 67.97; H, 4.75; N, 6.01.
À1
FAB-MS: m/z 913, IR (KBr pellet, cm ) 2926 (m C–H,
Compound 9b: kmax (loge) 429 (6.05), 550 (4.89), 592
À1
OCH
C H N (%): Calcd: C, 68.49; H, 4.86; N, 6.14. Found: C,
8.37; H, 4.75; N, 6.07.
3
), 1605 (m C@C Bz), 1505 (m Cp–Cp), 1245 (m C–O).
(4.17). FAB-MS: m/z 1041, IR (KBr pellet, cm ) 2935 (m
C–H, OCH ), 1578 (m C@C Bz), 1234 (m C–O). C H N (%):
3
6
Calcd: C, 64.67; H, 5.04; N, 5.39. Found: C, 64.57; H,
4.95; N, 5.27.
1
Compound 5e: H d 3.94–4.01 (m, 12H x, o-OCH
3
), 7.11–
7
.36 (m, 8H, phenyl), 7.53–7.74 (m, 4H, phenyl), 8.60–8.63
Compound 10b: kmax (loge) 429 (5.97), 550 (4.77), 587
(3.95). FAB-MS: m/z 1041, IR (KBr pellet, cm ) 2939 (m
1
3
À1
(
s, 8H, pyrrole); C d 55.9 (o-OCH ), 60.7, 60.8, 60.9 (m-
3
OCH
3
), 122.06, 127.06, 127.28, 127.67 (meso-C), 135.16
3
C–H, OCH ), 1607 (m C@C Bz), 1203 (m C–O). C H N (%):
Calcd: C, 64.67; H, 5.04; N, 5.39. Found: C, 64.57; H,
4.95; N, 5.27.
(b-C, pyrrole), 149.02 (a-C, pyrrole), 149.16, 152.3, 112.3,
1
5
14.5, 131.8, 142.5, 142.63, 142.67; kmax (loge) 414 (5.39),
27 (4.30), 559 (3.84). FAB-MS: m/z 921, C H N (%):
Compound 11b: kmax (loge) 429 (4.36), 549 (3.0), 583 (2.0).
À1
Calcd: C, 67.90; H, 4.82; N, 6.09. Found: C, 67.97; H,
.88; N, 6.01.
FAB-MS: m/z 881, IR (KBr pellet, cm ) 3048 (m Cp–H),
4
3026 (m C–H, Bz), 1578 (m C@C Bz). C H N (%): Calcd: C,
81.90; H, 4.12; N, 6.37. Found: C, 81.81; H, 4.10; N, 6.31.
Compound 12b: kmax (loge) 430 (5.7), 551 (4.4), 588 (3.6).
Compound 5f: kmax (loge) 416 (5.68), 538 (4.34), 573
À1
(
3.60). IR (KBr pellet, cm ) 2959, 2851 (m C–H, OCH3),
À1
1
(
4
600 (m C@C Bz), 1505 (m Cp–Cp), 1260 (m C–O). C H N
%): Calcd: C, 68.15; H, 4.84; N, 6.11. Found: C, 67.97; H,
.75; N, 6.83.
FAB-MS: m/z 881, IR (KBr pellet, cm ) 3057 (m Cp–H),
3026 (m C–H, Bz), 1578 (m C@C Bz). C H N (%): Calcd: C,
81.90; H, 4.12; N, 6.37. Found: C, 81.81; H, 4.10; N, 6.31.
Compound 12c: kmax (loge) 380 (4.6), 424 (4.9), 512 (41),
583 (3.53), 665 (3.53).
Compound 6b: kmax (loge) 429 (5.52), 464 (4.42), 550
À1
(
4.32). IR (KBr pellet, cm ) 2948 (m C–H, OCH
3
), 1600 (m
C@C Bz), 1515 (m Cp–Cp), 1256 (m C–O). C H N (%):
Calcd: C, 67.90; H, 4.82; N, 6.09. Found: C, 67.97; H,
Compound 13b: kmax (loge) 428 (6.0), 551 (4.94), 584
(3.74), 642 (3.32). IR (KBr pellet, cm ) 3062(m Cp–H),
À1
4
.75; N, 6.01.
3021 (m C–H, Bz), 1572 (m C@C Bz). C H N (%): Calcd: C,
84.41; H, 4.11; N, 5.19. Found; C 84.49, H 4.09, N 5.14.
Compound 13f: kmax (loge) 425 (5.55), 543 (4.63), 579
(4.11). IR (KBr pellet, cm ) 3048 (m Cp–H), 3016 (m C–H,
Bz), 1578 (m C@C Bz). C H N (%): Calcd: C, 84.78; H,
4.12; N, 5.20. Found: C, 84.73; H, 4.09; N, 5.15.
Compound 6c: kmax (loge) 381 (4.5), 422 (4.7), 510 (4.0),
À1
582 (3.6), 690 (3.44). IR (KBr pellet, cm ) 2936 (m C–H,
À1
OCH ), 1605 (m C@C Bz), 1245 (m C–O) C H N (%): Calcd:
C, 66.14; H, 4.70; N, 5.93. Found: C, 66.07; H, 4.65; N,
3
5.87.