Table 4
1H NMR (CDCl3) and 13C NMR (CDCl3) data of new compounds prepared (2e25)
5
2
4
3
9
1
6
N3
O
2
7
4
10
8
S
1
5
Compound 1H NMR d (ppm)
13C NMR d (ppm)
2
3
4
5
6
7
4.25 (s, 1H), 3.96 (m, 1H), 3.51 (d, J ¼ 15.6 Hz, 1H), 3.35 (m, 1H), 3.24 (d, J ¼ 15.6 Hz, 1H), 173.7 (C-4), 72.6 (C-2), 55.1 (NCH2), 44.8 (2 ꢅ CH3), 44.2 (CH2N), 41.7 (C-1), 38.3 (CAd-2,8,9),
2.73 (m, 1H), 2.59 (m, 1H), 2.38 (s, 6H), 2.00e1.61 (m, 15H)
36.6 (CAd-4,6,10), 33.2 (C-5), 27.9 (CAd-3,5,7)
4.32 (d, J ¼ 1.3 Hz, 1H), 3.89 (m, 1H), 3.52 (dd, J ¼ 15.6, 1.3 Hz, 1H), 3.26 (d, J ¼ 15.6 Hz, 1H), 173.6 (C-4), 73.3 (C-2), 50.1 (CH2N), 47.4 (2 ꢅ NCH2), 45.5 (NCH2), 41.7 (C-1), 38.5
3.21 (m, 1H), 2.71e2.45 (m, 6H), 2.01e1.60 (m, 15H), 1.04 (t, J ¼ 7.2 Hz, 6H)
(CAd-2,8,9), 36.7 (CAd-4,6,10), 33.3 (C-5), 28.0 (CAd-3,5,7), 12.0 (2 ꢅ CH3)
4.32 (s, 1H), 3.97 (m, 1H), 3.52 (d, J ¼ 15.6 Hz, 1H), 3.26 (d, J ¼ 15.6 Hz, 1 þ 1H), 2.58e2.29 173.7 (C-4), 72.8 (C-2), 55.8 (CH2N), 54.7 (2 ꢅ NCH2), 44.5 (C-1), 41.7 (NCH2), 38.4
(m, 6H), 2.01e1.40 (m, 15H þ 6H)
(CAd-2,8,9), 36.6 (CAd-4,6,10), 33.4 (C-5), 28.0 (CAd-3,5,7), 25.9 (2 ꢅ CH2), 24.14 (CH2)
4.27 (s, 1H), 4.00 (m, 1H), 3.68 (m, 6H), 3.53 (dd, J ¼ 15.6, 1.2 Hz, 1H), 3.27 (d, J ¼ 15.6 Hz, 173.9 (C-4), 72.8 (C-2), 67.0 (2 ꢅ CH2O) 55.4 (CH2N), 53.7 (2 ꢅ NCH2), 44.1 (C-1), 41.7
1H), 2.64e2.49 (m, 5H), 2.02e1.60 (m, 15H)
(NCH2), 38.4 (CAd-2,8,9), 36.6 (CAd-4,6,10), 33.3 (C-5), 28.00 (CAd-3,5,7)
4.14 (s, 1H), 3.81 (m, 1H), 3.68 (m, 1H), 3.56 (d, J ¼ 15.7 Hz, 1H), 3.25 (d, H-11, J ¼ 15.7 Hz, 174.0 (C-4), 72.5 (C-2), 55.0 (CH2N), 44.3 (2 ꢅ CH3), 42.3 (NCH2), 41.8 (C-1), 38.2 (CAd-2,8,9),
1H), 2.94 (t, J ¼ 7.3 Hz, 2H), 2.74 (s, 6H), 2.00e1.60 (m, 15H þ 1H) 1.20 (t, 1H, J ¼ 7.3 Hz)
36.5 (CAd-4,6,10), 33.2 (C-5), 27.9 (CAd-3,5,7), 22.1 (CH2)
4.21 (d, J ¼ 1.2 Hz, 1H), 3.85 (m, 1H), 3.53 (dd, J ¼ 15.6, 1.2 Hz, 1H), 3.31 (d, J ¼ 15.6 Hz, 1H), 173.5 (C-4), 72.5 (C-2), 49.6 (CH2N), 46.5 (2 ꢅ NCH2), 45.2 (NCH2), 41.7 (C-1), 38.3
3.17 (m, 1H), 2.56 (q, J ¼ 7.2 Hz, 4H), 2.45 (m, 2H), 2.01e1.59 (m, 15H þ 2H), 1.03 (t, J ¼
(CAd-2,8,9), 36.6 (CAd-4,6,10), 33.4 (C-5), 28.0 (CAd-3,5,7), 24.1 (CH2), 11.2 (2 ꢅ CH3)
7.2 Hz, 6H)
7.33 (d, J ¼ 8.8 Hz, 2H), 7.09 (d, J ¼ 8.8 Hz, 2H), 4.83 (d, J ¼ 1.2 Hz, 1H), 3.76 (d, J ¼ 15.6 Hz, 171.8 (C-4), 160.8 (d, J ¼ 246 Hz, CeF), 136.3 (d, J ¼ 3.1Hz, CAreN), 127.3 (d, J ¼ 8.4 Hz,
8
1H), 3.51 (d, J ¼ 15.6 Hz, 1H), 1.93e1.44 (m, 15H)
2 ꢅ C), 116.0 (d, J ¼ 22 Hz, 2 ꢅ C), 74.3 (C-2), 41.6 (C-1), 38.6 (CAd-2,8,9), 36.6 (CAd-4,6,10),
33.3 (C-5), 28.0 (CAd-3,5,7)
9
7.37 (d, J ¼ 9.2 Hz, 2H), 7.31 (d, J ¼ 9.1 Hz, 2H), 4.85 (d, J ¼ 1.3 Hz, 1H), 3.76 (dd, J ¼ 16.1, 171.6 (C-4), 138.8 (CAreN), 132.2 (CeCl), 129.2 (2 ꢅ C), 126.8 (2 ꢅ C), 74.0 (C-2), 41.7 (C-1),
1.3 Hz, 1H), 3.50 (d, J ¼ 16.1 Hz, 1H), 1.93e1.43 (m, 15H)
38.6 (CAd-2,8,9), 36.6 (CAd-4,6,10), 33.4 (C-5), 28.0 (CAd-3,5,7)
10
11
12
13
14
7.52 (d, J ¼ 8.5 Hz, 2H), 7.25 (d, J ¼ 8.5 Hz, 2H), 4.85 (d, J ¼ 1.2 Hz, 1H), 3.75 (d, J ¼ 15.6 Hz, 171.6 (C-4), 139.4 (CAreN), 132.2 (2 ꢅ C), 127.1 (2 ꢅ C), 120.1 (CeBr), 74.0 (C-2), 41.8 (C-1),
1H), 3.50 (d, J ¼ 15.6 Hz, 1H), 1.93e1.43 (m, 15H)
38.6 (CAd-2,8,9), 36.5 (CAd-4,6,10), 33.4 (C-5), 28.0 (CAd-3,5,7)
7.71 (d, J ¼ 8.8 Hz, 2H), 7.12 (d, J ¼ 8.8 Hz, 2H), 4.85 (d, J ¼ 1.2 Hz, 1H), 3.74 (dd, J ¼ 15.6, 171.5 (C-4), 140.1 (CAreN), 138.2 (2 ꢅ C), 127.3 (2 ꢅ C), 91.36 (CeI), 73.9 (C-2), 41.8 (C-1),
1.2 Hz, 1H), 3.49 (d, J ¼ 15.6 Hz, 1H), 1.93e1.43 (m, 15H)
38.6 (CAd-2,8,9), 36.6 (CAd-4,6,10), 33.5 (C-5), 28.0 (CAd-3,5,7)
7.70 (d, J ¼ 9.0 Hz, 2H), 7.53 (d, J ¼ 9.0 Hz, 2H), 4.93 (s, 1H), 3.78 (d, J ¼ 16.3 Hz, 1H), 3.52 (d, 171.5 (C-4), 144.2 (CAreN), 133.0 (2 ꢅ C), 125.6 (2 ꢅ C), 118.3 (C^N), 110.0 (CeCN), 73.4
J ¼ 16.3 Hz, 1H), 1.94e1.40 (m, 15H)
(C-2), 42.1 (C-1), 38.7 (CAd-2,8,9), 36.5 (CAd-4,6,10), 33.5 (C-5), 27.9 (CAd-3,5,7)
7.25 (d, J ¼ 9.1 Hz, 2H), 6.91 (d, J ¼ 9.1 Hz, 2H), 4.82 (d, J ¼ 1.5 Hz, 1H), 3.81 (s, 3H), 3.75 (dd 171.8 (C-4), 158.0 (CeOMe), 132.2 (CAreN), 126.8 (2 ꢅ C), 114.2 (2 ꢅ C), 74.4 (C-2), 55.2
J ¼ 15.7, 1.5 Hz, 1H), 3.50 (d, J ¼ 15.7 Hz, 1H), 1.92e1.46 (m, 15H)
(OCH3), 41.4 (C-1), 38.5 (CAd-2,8,9), 36.6 (CAd-4,6,10), 33.3 (C-5), 28.0 (CAd-3,5,7)
7.68 (d, J ¼ 1.6 Hz, 2H), 7.54 (m, 2H), 4.87 (d, J ¼ 1.2 Hz, 1H), 3.77 (dd, J ¼ 16.0, 1.2 Hz, 1H), 171.7 (C-4), 132.1 (CeCl, CAr), 130.0 (CAr), 128.6 (q, J ¼ 32 Hz, CeCF3), 124.1 (q, J ¼ 5 Hz,
3.52 (d, J ¼ 16 Hz, 1H), 1.95e1.42 (m, 15H)
CAr), 122.3 (q, J ¼ 272 Hz, CF3), 73.7 (C-2), 41.9 (C-1), 38.7 (CAd-2,8,9), 36.5 (CAd-4,6,10),
33.3 (C-5), 27.9 (CAd-3,5,7)
15
16
8.39 (ddd, J ¼ 4.9, 2.0, 0.8 Hz, 1H), 7.84 (ddd, J ¼ 8.1, 1.2, 0.8 Hz, 1H), 7.75 (ddd, J ¼ 8.1, 7.3, 171.2 (C-4), 152.4, 147.4, 138.0, 121.0, 118.5 (CAr), 70.4 (C-2), 41.7 (C-1), 38.3 (CAd-2,8,9),
2 Hz, 1H), 7.11 (ddd, J ¼ 7.3, 4.9, 1.2 Hz, 1H), 5.88 (d, J ¼ 1.0 Hz, 1H), 3.83 (dd, J ¼ 16.2,
1.0 Hz, 1H), 3.52 (d, J ¼ 16.2 Hz, 1H), 1.91e1.39 (m, 15H)
36.6 (CAd-4,6,10), 35.0 (C-5), 28.0 (CAd-3,5,7)
8.66 (d, J ¼ 2.5 Hz, 1H), 8.48 (dd, J ¼ 4.8, 1.3 Hz, 1H), 7.74 (ddd, J ¼ 8.4, 2.5, 1.3 Hz, 1H), 7.36 171.8 (C-4), 147.2, 146.4, 137.1, 132.8, 123.6 (CAr), 73.6 (C-2), 41.8 (C-1), 38.7 (CAd-2,8,9),
(dd, J ¼ 8.4, 4.8 Hz, 1H), 4.92 (d, J ¼ 1.4 Hz, 1H), 3.77 (dd, J ¼ 15.8, 1.4 Hz, 1H), 3.52 (d, J ¼ 36.5 (CAd-4,6,10), 33.2 (C-5), 27.9 (CAd-3,5,7)
15.8 Hz, 1H), 1.92e1.42 (m, 15H)
17
18
8.64 (d, J ¼ 6.0 Hz, 2H), 7.50 (dd, J ¼ 6.0 Hz, 2H), 4.99 (s, 1H), 3.79 (dd, J ¼ 16.0, 1.0 Hz, 1H), 171.8 (C-4), 149.8, 118.6 (CAr), 72.4 (C-2), 42.5 (C-1), 38.7 (CAd-2,8,9), 36.7 (CAd-4,6,10), 33.8
3.53 (d, J ¼ 16.0 Hz, 1H), 1.95e1.42 (m, 15H)
(C-5), 27.9 (CAd-3,5,7)
8.30 (d, J ¼ 4.3 Hz, 1H), 7.60 (ddd, J ¼ 7.7, 0.8 Hz, 1H), 7.16 (dd, J ¼ 7.7, 4.3 Hz, 1H), 5.51
(s, 1H), 3.79 (ddd, J ¼ 15.2, 0.8 Hz, 1H), 3.46 (d, J ¼ 15.2 Hz, 1H), 2.36 (s, 3H), 1.92e1.44
(m, 15H)
172.0 (C-4), 152.1, 145.8, 140.4, 130.2, 122.7 (CAr), 72.6 (C-2), 41.0 (C-1), 38.1 (CAd-2,8,9),
36.7 (CAd-4,6,10), 33.8 (C-5), 28.0 (CAd-3,5,7), 18.5 (CH3)