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[8] 3-Amino-5-iodobenzyl alcohol (2) mp 66–68 8C; 1H NMR (300 MHz, CDCl3): d 2.07 (br, 1H), 3.92 (br, 2H), 4.81 (s, 2H), 6.45 (s, 1H), 6.86 (s,
1H), 7.02 (s, 1H); IR (film): 3370, 2974, 2872, 749 cmÀ1. 3-Azido-5-iodobenzyl alcohol (3) mp 89–91 8C; 1H NMR (300 MHz, CDCl3): d 1.91
(br, 1H), 4.71 (s, 2H), 7.09 (s, 1H), 7.47 (s, 1H), 7.67 (s, 1H); IR (film): 3330, 2980, 2878, 2113, 789 cmÀ1. 3-Nitro-5-(2-(trimethylsily-
l)ethynyl)benzyl alcohol (4) mp 82–84 8C; 1H NMR (300 MHz, CDCl3): d 0.26 (s, 9H), 1.95 (br, 1H), 4.79 (s, 2H), 7.76 (s, 1H), 8.17 (s, 1H), 8.20
(s, 1H); IR (film): 3305, 2968, 2165, 1535, 1347 cmÀ1. 3-Amino-5-(2-(trimethylsilyl)ethynyl)benzyl alcohol (5) mp 78–80 8C; 1H NMR
(300 MHz, CDCl3): d 0.23 (s, 9H), 2.70–3.25 (br, 3H), 4.56 (s, 2H), 6.67 (s, 1H), 6.72 (s, 1H), 6.87 (s, 1H); IR (film): 3365, 2975, 2873,
2161 cmÀ1. 3-Azido-5-(2-(trimethylsilyl)ethynyl)benzyl alcohol (6) mp 88–90 8C; 1H NMR (300 MHz, CDCl3): d 0.25 (s, 9H), 2.11 (br, 1H),
4.62 (s, 2H), 6.96 (s, 1H), 7.02 (s, 1H), 7.20 (s, 1H); IR (film): 3308, 2974, 2872, 2163, 2118 cmÀ1; HR-MS (ESI) calcd. for C12H15N3OSi (M+):
245.0984, found: 245.0982. 4-(3,5-Dioxo-4-aza-tricyclo[5.2.1.02,6]dec-8-en-4-yl)-bromide (8) mp 153–155 8C (Lit. [7] 156 8C); 1H NMR
(400 MHz, CDCl3): d 1.59 (d, 1H, J = 8.8 Hz), 1.77 (d, 1H, J = 8.8 Hz), 3.41–3.42 (m, 2H), 3.48–3.50 (m, 2H), 6.23 (t, 2H, J = 1.8 Hz), 7.02 (d,
2H, J = 8.6 Hz), 7.53 (d, 2H, J = 8.6 Hz). 4-(4-Azatricyclo[5.2.1.02.6]dec-8-en-4-yl)-phenyl bromide (9) mp 156–158 8C; 1H NMR (400 MHz,
CDCl3): d 1.50 (d, 1H, J = 8.2 Hz), 1.60 (d, 1H, J = 8.2 Hz), 2.82–2.85 (m, 2H), 2.95–2.96 (m, 2H), 3.04–3.07 (m, 2H), 3.15–3.20 (m, 2H), 6.14
(t, 2H, J = 1.9 Hz), 6.28 (d, 2H, J = 8.8 Hz), 7.23 (d, 2H, J = 8.8 Hz); 13C NMR (100 MHz, CDCl3): d 45.5, 46.5, 50.6, 52.1, 107.2, 113.4, 131.6,
135.8, 146.4; IR (film): 3056, 2970, 2955, 2887,1592, 1503, 1475, 1374, 793, 722 cmÀ1. HR-MS (FAB) calcd. for C15H16BrN (M+): 289.0466,
Found: 289.0467. 4-(4-Azatricyclo[5.2.1.02.6]dec-8-en-4-yl)-benzoic acid (10) mp 306–308 8C (Lit. [3d]. 310 8C, dec.); 1H NMR (400 MHz,
DMSO-d6): d 1.48 (s, 2H), 2.88–2.91 (m, 2H), 2.94–2.95 (m, 2H), 3.05–3.07 (m, 2H), 3.21–3.23 (m, 2H), 6.15 (t, 2H, J = 1.9 Hz), 6.40 (d, 2H,
J = 8.9 Hz), 7.69 (d, 2H, J = 8.9 Hz); 13C NMR (100 MHz, DMSO-d6): d 44.8, 46.1, 50.1, 51.6, 110.9, 116.3, 130.9, 135.8, 150.0, 167.6; HR-MS
(FAB) calcd. for C16H17NO2 (M+): 255.1259, found: 255.1264. Monomer 11 mp 172–174 8C; 1H NMR (300 MHz, CDCl3): d 0.25 (s, 9H), 1.52
(d, 1H, J = 8.6 Hz), 1.62 (d, 1H, J = 8.6 Hz), 2.94–3.33 (m, 8H), 5.23 (s, 2H), 6.16 (s, 2H), 6.39 (d, 2H, J = 8.7 Hz), 7.01 (s, 1H), 7.07 (s, 1H),
7.28 (s, 1H), 7.89 (d, 2H, J = 8.7 Hz); 13C NMR (75 MHz, CDCl3): d À0.2, 45.4, 46.6, 50.5, 52.1, 64.1, 95.5, 103.6, 110.8, 116.6, 117.4, 121.1,
124.7, 126.6, 131.2, 135.8, 140.4, 142.9, 150.3, 168.3; IR (film): 2967, 2939, 2856, 2160, 2116, 1693, 1608, 1525, 1479 1384, 1364, 1278 cmÀ1
;
HR-MS (FAB) calcd. for C28H30N4O2Si (M+): 482.2138, found: 482.2134. Polymer 12 1H NMR (300 MHz, CDCl3): d 0.23 (brs, 9 H), 1.32 (brs,
1 H), 1.83 (brs, 1 H), 2.73 (brs, 2 H), 2.89 (brs, 2 H), 3.24 (brs, 4 H), 5.20 (brs, 2 H), 5.36 (brs, 2 H), 6.48 (brs, 2 H), 6.99 (brs, 1 H), 7.04 (brs, 1 H),
7.25 (brs, 1 H), 7.89 (brs, 2 H); IR (KBr): 2965, 2930, 2162, 2114, 1720, 1606, 1527, 1350, 1271, 720 cmÀ1; GPC (THF): Mn = 17800;
PDI = 1.36. Polymer 13 1H NMR (300 MHz, CDCl3): d 1.31 (brs, 1H), 1.87 (brs, 1H), 2.73–2.92 (brs, 4H), 3.31 (brs, 5H), 5.22 (brs, 2H), 5.34
(brs, 2H), 6.56 (brs, 2H), 6.99–7.05 (brs, 2H), 7.25 (brs, 1H), 7.92 (brs, 2H); IR (KBr): 3323, 2963, 2932, 2130, 2110, 1721, 1604, 1528, 1353,
1270, 721 cmÀ1; GPC (THF): Mn = 15100; PDI = 1.36.