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(C-2), 131.6 (Ca), 130.8 (C-7a), 124.2 (C-3), 121.9 (C-3a),
H-4, 3J3–4 4.0 Hz), 5.40 (d, 1H, HA, 3JA–X 8.4 Hz), 5.24 (d,
3
106.7 (Cb), 24.7 (C-4), 23.0 (C-7), 22.7 (C-5, C-6). IR (thin
film, KBr plate): 3125, 3088, 2933, 2854, 2784, 2716, 1655,
1638, 1565, 1481, 1462, 1440, 1424, 1394, 1372, 1329, 1288,
1257, 1241, 1212, 1160, 1132, 1105, 1083, 1059, 970, 945,
869, 833, 815, 743, 705, 686, 636, 551, 486 cmꢀ1. Anal.
Calcd for C11H13NO (175.23): C, 75.40; H, 7.48; N 7.99.
Found: C, 75.21; H, 7.62; N, 8.03.
1H, HB, JB–X 15.7 Hz). 13C NMR (101.61, CDCl3): d
179.20 (C@O), 135.15 (C-20), 133.53 (C-2), 132.43 (C-50),
130.87 (Ca), 127.91 (C-5), 127.55 (C-4), 127.01 (C-30),
123.28 (C-3), 114.66 (Cb), 112.80 (C-4). IR (thin layer):
3106, 3077, 2992, 2846, 2817, 2791, 2726, 1669, 1655, 1640,
1592, 1563, 1511, 1470, 1435, 1411, 1362, 1330, 1113, 1292,
1230, 1199, 1094, 1076, 1038, 1006, 958, 906, 847, 786, 747,
704, 670, 634, 616, 581, 501, 461 cmꢀ1. Anal. Calcd for
C11H9NOS (203.26): C, 65.00; H, 4.46; N 6.89, S 15.77.
Found: C, 65.11; H, 4.34; N 6.68, S 15.91.
5-Phenyl-1-vinylpyrrole-2-carbaldehyde (2b). Yield 66%.
Yellowish oil, n2D3 1.6550. 1H NMR (400.13 MHz, CDCl3):
d 9.63 (s, 1H, HCHO), 7.42 (m, 5H, Ph) 7.40 (dd, 1H, HX,
3
3
3JB–X 15.9 Hz, JA–X 8.7 Hz), 7.07 (d, 1H, H-3, J3–4
1-Vinyl-4,5-dihydrobenzo[g]indole-2-carbaldehyde
(2e).
3
3.9 Hz), 6.34 (d, 1H, H-4, J3–4 3.9 Hz), 5.10 (d, 1H, HA,
Yield 91%. Beige crystals, mp. 133–135 ꢀC. 1H NMR
(400.13 MHz, CDCl3): d 9.54 (s, 1H, HCHO), 7.70 (d, 1H,
H-6, 3J6–7 8.1 Hz), 7.50 (dd, 1H, HX, 3JB–X 15.7 Hz, 3JA–X
8.3 Hz), 7.23 (d, 1H, H-9, 3J8–9 9.1 Hz), 7.14 (m, 2H, H-7,
3JA–X 8.7 Hz), 4.87 (d, 1H, HB, 3JB–X 15.9 Hz). 13C NMR
(101.6, CDCl3): d 179.5 (C@O), 142.3 (C-2), 133.3 (Ci),
131.5 (C-5), 131.2 (Cp), 129.3 (Cm), 128.5 (Co), 128.5 (C-3),
124.4 (C-4), 112.7 (Ca), 112.6 (Cb). IR (thin film, KBr
plate): 3121, 3065, 3027, 2985, 2928, 2803, 2721, 1655,
1636, 1595, 1564, 1530, 1497, 1453, 1440, 1421, 1350, 1328,
1288, 1223, 1065, 1033, 949, 919, 895, 869, 837, 788, 746,
686, 663, 606, 531, 462 cmꢀ1. Anal. Calcd for C13H11NO
(197.23): C, 79.16; H, 5.62; N 7.10. Found: C, 79.05; H,
5.92; N, 7.42.
3
H-8), 6.84 (s, 1H, H-3), 5.37 (d, 1H, HA, JA–X 8.3 Hz),
3
3
5.36 (d, 1H, HB, JB–X 15.7 Hz), 2.88 (t, 2H, H-4, J4–5
7.2 Hz), 2.66 (t, 2H, H-5, 3J4–5 7.2 Hz). 13C NMR (101.61,
CDCl3): d 178.5 (C@O), 138.3 (C-5a), 136.2 (C-9b), 133.6
(C-2), 132.5 (Ca), 128.7 (C-7), 127.8 (C-9a), 127.6 (C-6),
126.4 (C-8), 125.1 (C-3a), 124.2 (C-9), 121.2 (C-3), 113.7
(Cb), 30.6 (C-5), 22.1 (C-4). IR (KBr): 3098, 3028, 2982,
2961, 2894, 2834, 1640, 1606, 1535, 1504, 1467, 1436, 1416,
1373, 1335, 1297, 1278, 1236, 1185, 1158, 1136, 1094, 1045,
1027, 982, 943, 926, 913, 867, 839, 778, 762, 738, 716, 683,
664, 637, 599, 574, 549, 522, 471, 437 cmꢀ1. Anal. Calcd
for C15H13NO (223.27): C, 80.69; H, 5.87; N 6.27. Found:
C, 80.81; H, 6.14; N 6.07.
5-(4-Methoxyphenyl)-1-vinylpyrrole-2-carbaldehyde (2c).
Yield 82%. Yellowish crystals, mp 74–76 ꢀC. 1H NMR
(400.13 MHz, CDCl3): d 9.55 (s, 1H, HCHO), 7.40 (dd, 1H,
3
3
3
HX, JB–X 15.9 Hz, JA–X 8.7 Hz), 7.30 (d, 2H, Ho, Jo–m
3
9.0 Hz), 6.96 (d, 1H, H-3, J3–4 3.9 Hz), 6.86 (d, 2H, Hm,
3Jo–m 9.0 Hz), 6.24 (d, 1H, H-4, 3J3–4 3.9 Hz), 5.05 (d, 1H,
3
3
HA, JA–X 8.7 Hz), 4.85 (d, 1H, HB, JB–X 15.9 Hz), 3.81
(s, 3H, Me). 13C NMR (101.6 MHz, CDCl3): d 179.2
(C@O), 159.9 (Cp), 142.4 (C-2), 133.2 (Ci), 131.3 (Ca),
130.6 (Co), 124.5 (C-3), 123.9 (C-5), 114.0 (Cm), 112.2 (Cb,
C-4), 55.4 (Me). IR (KBr): 2967, 2924, 2828, 1638, 1597,
1565, 1523, 1497, 1440, 1421, 1375, 1333, 1308, 1288, 1223,
1165, 1099, 1023, 1004, 944, 910, 817, 786, 757, 730, 709,
676, 643, 586, 521, 434 cmꢀ1. Anal. Calcd for C14H13NO2
(227.26): C, 73.99; H, 5.77; N 6.16. Found: C, 73.87; H,
5.81; N, 6.23.
15. (a) Trofimov, B. A.; Korostova, S. E.; Mikhaleva, A. I.;
Sobenina, L. N.; Vasil’ev, A. N. Khim. Geterotsikl. Soed.
1982, 1631–1639; (b) Trofimov, B. A.; Korostova, S. E.;
Shevthenko, S. G.; Mikhaleva, A. I.; Matel’, N. L. Zh.
Org. Khim. 1996, 32, 897–899.
16. (a) Sigalov, M. V.; Shmidt, E. Yu.; Trofimov, B. A. Izv.
AN SSSR. Ser. Khim. 1987, 1146–1149; (b) Sigalov, M. V.;
Shmidt, E. Yu.; Trofimov, B. A. Khim. Geterotsikl. Soed.
1988, 334–338; (c) Sigalov, M. V.; Shmidt, E. Yu.;
Korostova, S. E.; Trofimov, B. A. Khim. Geterotsikl.
Soed. 1991, 1041–1045; (d) Sigalov, M. V.; Trofimov, A.
B.; Shmidt, E. Yu.; Trofimov, B. A. J. Phys. Org. Chem.
1993, 6, 471–477; (e) Sigalov, M. V.; Shmidt, E. Yu.;
Mikhaleva, A. I.; Korostova, S. E.; Lazarev, I. M.;
Trofimov, B. A. Khim. Geterotsikl. Soed. 1993, 48–57; (f)
Trofimov, B. A.; Sigalov, M. V. Main Group Chem. News
1998, 6, 30–41.
5-(2-Thienyl)-1-vinylpyrrole-2-carbaldehyde (2d). Yield
88%. Cherry coloured crystals, mp. 34–35 ꢀC. 1H NMR
(400.13 MHz, CDCl3): d 9.61 (s, 1H, HCHO), 7.36 (dd, 1H,
H-30, 3J3–34, 5.1 Hz, 3J3–5, 1.1 Hz), 7.25 (dd, 1H, HX, 3JB–X
3
15.7 Hz, JA–X 8.4 Hz), 7.20 (dd, 1H, H-40, J3–4, 5.1 Hz,
3
3
3
0
J4–5 3.6 Hz), 7.06 (dd, 1 H,H5 , J4–5 3.6 Hz, J3–5
,
3
1.1 Hz), 7.04 (d, 1H, H-3, J3–4 4.0 Hz), 6.45 (d, 1H,