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PAPER
Table 2 Spectral Data for Compounds 2–5, 9–11 and 13 (continued)
Compd IR (cm–1) NMR (d, ppm)a
3c
3450, 3424, 2950, 2870, 2791, 2616, 2478, 2438,
1717, 1555, 1493, 1458, 1408, 1371, 1301, 1279,
1H NMR: 1.66 (tdd, J = 6.9, 7.4, 12.8 Hz, 1 H, 4¢¢-Ha), 2.03 (dtd, J = 5.5, 7.8,
12.8 Hz, 1 H, 4¢¢-Hb), 2.58 (br sept., J = 7.0 Hz, 1 H, 3¢¢-H), 2.96 (br s, 2 H,
1232, 1190, 1157, 1130, 1109, 1080, 1029, 992, 941, CHCH2N), 3.07 (br s, 2 H, 1¢-CH2), 3.35–3.43 (m, 2 H, 2¢-CH2), 3.50 (dd,
902, 865, 807, 787, 751, 710, 652, 609, 542, 459, 414 J = 5.8, 8.8 Hz, 1 H, 2¢¢-Ha), 3.64 (q, J = 7.6 Hz, 1 H, 5¢¢-Ha), 3.72 (dd,
J = 6.3, 7.4 Hz, 1 H, 5¢¢-Hb), 3.74 (s, 3 H, 1-CH3), 3.77 (t, J = 8.7 Hz, 1 H, 2¢¢-
+
Hb), 3.89 (s, 3 H, OCH3), 7.81 (s, 1 H, 3-H), 9.21 (br s, 2 H, NH2 )
13C NMR: 21.0, 29.9, 35.9, 36.8, 45.0, 49.2, 51.0, 66.7, 70.4, 111.2, 139.9,
142.0, 163.0
3d
3e
3f
3437, 3172, 2828, 2797, 2739, 2701, 2597, 2506,
2459, 2334, 2055, 1704, 1598, 1564, 1500, 1460,
1435, 1395, 1374, 1339, 1299, 1282, 1249, 1186,
1166, 1130, 1110, 1079, 1059, 1023, 981, 949, 924,
890, 810, 795, 777, 745, 705, 655, 543, 511, 467
1H NMR: 1.26 [d, J = 6.5 Hz, 6 H, (CH3)2CH], 3.00–3.10 (m, 2 H, 1¢-CH2),
3.30–3.40 [m, 3 H, CH(CH3)2 and 2¢-CH2], 3.77 (s, 3 H, 1-CH3), 3.89 (s, 3 H,
+
OCH3), 7.81 (s, 1 H, 3-H), 9.21 (br s, 2 H, NH2 )
3470, 2992, 2951, 2927, 2845, 2807, 2751, 2663,
2615, 2477, 2360, 1964, 1905, 1824, 1713, 1634,
1595, 1557, 1502, 1454, 1440, 1413, 1379, 1306,
1258, 1230, 1196, 1096, 1029, 972, 918, 877, 808,
783, 757, 744, 698, 653, 593, 492, 441
1H NMR: 3.05–3.13 (m, 2 H, 1¢-CH2), 3.28–3.36 (m, 2 H, 2¢-CH2), 3.80 (s,
3 H, OCH3), 4.09 (br s, 2 H, CH2Ph), 7.39–7.44 (m, 3 H, 3H of Ph), 7.44–7.54
(m, 4 H, 4H of Ph), 7.56–7.61 (m, 3 H, 3H of Ph), 8.08 (s, 1 H, 3-H), 9.33 (br
+
s, 2 H, NH2 )
3418, 2984, 2945, 2831, 2604, 2570, 2466, 2407,
2013, 1958, 1702, 1634, 1560, 1495, 1454, 1414,
1375, 1311, 1269, 1105, 1070, 1005, 975, 933, 874, H), 7.51 (dd, J = 2.0, 7.4 Hz, 1 H, 3¢¢-H), 7.51–7.54 (m, 1 H, p-PhH), 7.55–
810, 777, 700, 623, 598, 486, 444
1H NMR: 3.17–3.25 (m, 2 H, 1¢-CH2), 3.33–3.41 (m, 2 H, 2¢-CH2), 3.81 (s,
3 H, OCH3), 4.29 (br s, 2 H, CH2Py), 7.47 (ddd, J = 1.0, 5.0, 7.5 Hz, 1 H, 5¢¢-
7.61 (m, 4 H, o,m-PhH), 7.92 (dt, J = 1.8, 7.7 Hz, 1 H, 4¢¢-H), 8.08 (s, 1 H, 3-
+
H), 8.62 (ddd, J = 0.9, 1.6, 4.9 Hz, 1 H, 6¢¢-H), 9.64 (br s, 2 H, NH2 )
3g
3455, 3088, 2947, 2852, 2767, 2704, 2607, 2434,
1715, 1595, 1548, 1499, 1458, 1434, 1404, 1242,
1092, 1043, 972, 910, 772, 693
1H NMR: 1.59 (tdd, J = 6.9, 7.6, 12.6 Hz, 1 H, 4¢¢-Ha), 1.98 (dtd, J = 5.4, 7.9,
12.8 Hz, 1 H, 4¢¢-Hb), 2.49 (br sept., J = 7.0 Hz, 1 H, 3¢¢-H), 2.87 (br s, 2 H,
CHCH2N), 3.10 (br s, 2 H, 1¢-CH2), 3.26–3.35 (m, 2 H, 2¢-CH2), 3.42 (dd,
J = 5.9, 8.8 Hz, 1 H, 2¢¢-Ha), 3.61 (q, J = 7.7 Hz, 1 H, 5¢¢-Ha), 3.71 (t, J = 8.5
Hz, 1 H, 2¢¢-Hb), 3.73 (dd, J = 7.0, 8.1 Hz, 1 H, 5¢¢-Hb), 3.83 (s, 3 H, OCH3),
+
7.52–7.65 (m, 5 H, PhH), 8.09 (s, 1 H, 3-H), 9.10 (br s, 2 H, NH2 )
13C NMR: 21.6, 29.8, 35.7, 44.8, 48.9, 51.4, 66.7, 70.3, 112.5, 126.0, 129.3,
129.6, 138.0, 141.4, 142.6, 163.0
3h
3418, 2963, 2833, 2711, 2601, 2457, 2052, 1711,
1595, 1556, 1497, 1462, 1438, 1404, 1300, 1256,
1213, 1188, 1134, 1087, 1065, 1001, 966, 809, 772, (m, 5 H, PhH), 8.09 (s, 1 H, 3-H), 8.98 (br s, 2 H, NH2 )
1H NMR: 1.18 [d, J = 6.5 Hz, 6 H, (CH3)2CH], 3.02–3.11 (m, 2 H, 1¢-CH2),
3.15–3.33 [m, 3 H, 2¢-CH2 and CH(CH3)2], 3.83 (s, 3 H, OCH3), 7.52–7.64
+
694, 656, 616, 503, 463
13C NMR: 18.3, 22.0, 41.3, 48.8, 51.4, 112.5, 126.0, 129.2, 129.6, 138.0,
141.5, 142.6, 163.0
3i
3j
3422, 3129, 2955, 2772, 2701, 2363, 1868, 1724,
1645, 1582, 1549, 1499, 1472, 1436, 1391, 1298,
1237, 1192, 1151, 1098, 1032, 878, 802, 781, 737,
702, 608, 490, 458
1H NMR: 1.62 (s, 9 H, t-Bu), 3.05–3.18 (m, 2 H, 1¢-CH2), 3.56–3.64 (m, 2 H,
2¢-CH2), 3.73 (s, 3 H, OCH3), 4.22 (br t, J = 5.9 Hz, 2 H, CH2Ph), 7.40–7.49
(m, 3 H, o,p-PhH), 7.58–7.63 (m, 2 H, p-PhH), 7.79 (s, 1 H, 3-H), 9.77 (br s,
+
2 H, NH2 )
3453, 2948, 2776, 2479, 1707, 1549, 1464, 1437,
1400, 1374, 1277, 1238, 1215, 1150, 1098, 1046,
984, 933, 868, 810, 781, 615, 470
1H NMR: 1.65 (s, 9 H, t-Bu), 1.69 (tdd, J = 6.9, 7.6, 12.4 Hz, 1 H, 4¢¢-Ha),
2.06 (dtd, J = 5.4, 7.9, 12.4 Hz, 1 H, 4¢¢-Hb), 2.61 (br sept., J = 7.1 Hz, 1 H,
3¢¢-H), 3.01 (br s, 2 H, CHCH2N), 3.10 (br s, 2 H, 1¢-CH2), 3.51 (dd, J = 5.9,
8.8 Hz, 1 H, 2¢¢-Ha), 3.55–3.63 (m, 2 H, 2¢-CH2), 3.65 (q, J = 7.7 Hz, 1 H, 5¢¢-
Ha), 3.71–3.81 (m, 2 H, 2¢¢-Hb and 5¢¢-Hb), 3.77 (s, 3 H, OCH3), 7.80 (s, 1 H,
+
3-H), 9.40 (br s, 2 H, NH2 )
3k
4a
3439, 2972, 2949, 2833, 2801, 2740, 2698, 2648,
2597, 2569, 2507, 2458, 2327, 2052, 1710, 1587,
1553, 1467, 1442, 1400, 1373, 1298, 1275, 1238,
1H NMR: 1.28 [d, J = 6.5 Hz, 6 H, (CH3)2CH], 1.65 (s, 9 H, t-Bu), 3.09 (m,
2 H, 1¢-CH2), 3.29–3.41 [m, 1 H, CH(CH3)2], 3.50–3.59 (m, 2 H, 2¢-CH2),
+
3.77 (s, 3 H, OCH3), 7.80 (s, 1 H, 3-H), 9.19 (br s, 2 H, NH2 )
1211, 1152, 1099, 1052, 1028, 1009, 981, 945, 925, 13C NMR: 18.4, 22.9, 30.1, 42.2, 49.0, 51.1, 61.3, 112.9, 138.4, 141.5, 163.1
866, 828, 810, 781, 769, 740, 613, 555, 529, 467
3445, 3426, 3102, 3026, 2949, 2921, 2434, 1915,
1792, 1653, 1552, 1526, 1479, 1453, 1422, 1361,
1336, 1288, 1231, 1159, 1067, 1045, 1028, 1002,
980, 936, 903, 862, 800, 772, 748, 702, 671, 645,
614, 554, 489, 469, 453
1H NMR: 2.94 (t, J = 6.9 Hz, 2 H, 7-CH2), 3.50 (t, J = 6.9 Hz, 2 H, 6-CH2),
3.74 (s, 3 H, 1-CH3), 4.61 (s, 2 H, CH2Ph), 7.22–7.36 (m, 5 H, PhH), 7.69 (s,
1 H, 3-H)
13C NMR: 21.0, 36.1, 45.8, 49.0, 113.9, 127.5, 128.1, 128.7, 137.8, 138.0,
142.8, 162.9
Synthesis 2010, No. 19, 3363–3373 © Thieme Stuttgart · New York