absolute pyridine under an atmosphere of argon. The solution
was stirred for 2 h under reflux and subsequently filtered over
10 g of alumina. The alumina was thoroughly washed with
dichloromethane. The washing solution and the filtrate were
combined and the solvent was removed under reduced
pressure. The resulting black solid was dissolved in 20 mL
dichloromethane and precipitated by the addition of acetone.
This procedure was repeated twice. Finally, the product was
dried in vacuum at 50 1C for several hours to yield 41.2 mg of
10 (76%) as a dark green solid. IR (KBr, cmꢁ1): 2959 s,
2923 vs, 2853 s, 1620 m, 1532 vs, 1480 s, 1464 s, 1378 m, 1318 m,
1261 vs, 1100 vs, 1038 vs, 950 w, 916 w, 897 w, 802 vs, 754 m,
703 w, 620 w 475 w, 461 w, 412 w. 1H NMR (CDCl3,
400.13 MHz): d = 0.88–0.92 (m, 24H, H-h), 1.32–1.52
(m, 80H, H-g–H-c), 1.80–1.87 (m, 16H, H-b), 2.12–2.14
(m, 4H, H-py1), 2.85–2.88 (m, 16H, H-a), 5.10–5.14 (m, 4H,
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H-py2), 6.00–6.03 (m, 2H, H-py3), 6.26 (d, JH,H = 2.2 Hz,
8H, H-2), 7.25 (d, 3JH,H = 2.2 Hz, 8H, H-3), 9.49 (s, 8H, H-5).
13C NMR (CDCl3, 150.92 MHz): d = 14.3 (C-h), 22.9 (C-g),
28.6 (C-f), 29.5 (C-e), 29.6 (C-d), 29.7 (C-c), 29.8 (C-b), 32.1
(C-a), 107.0 (C-2), 119.8 (C-5), 121.8 (C-py2), 131.7 (C-3), 134.1
(C-py3), 135.3 (C-4), 140.9 (C-6), 147.7 (C-7), 149.7 (C-py1),
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532 | New J. Chem., 2010, 34, 526–532