906
M. Z. Gao, J. H. Reibenspies, B. Wang, Z. L. Xu and R. A. Zingaro
Vol. 41
CH), 4.25-4.98 (4H, m, CH O), 7.18-7.27 (10H, m, phenyl-H),
2
δ : 0.93, 1.03 (12H, 2d, J=7.0Hz, CH ), 2.01-2.08 (2H, m, CH),
H
4.09-4.16 (4H, m, CH O and CH),5.22-5.25 (2H, dd, J=3.0, 11.2Hz,
3
8.21-8.45 (6H, m, pyridyl-H), 8.60 (2H, d, J = 7.8Hz, CONH);
MS(FAB): 565 (M+1, 24%), 239, 57, 55.
Anal. Calcd. for C H N O : C, 68.07; H, 5.00; N, 9.92.
2
CH O), 8.58-8.60 (2H, d, J=8.5Hz, CONH), 7.73-9.09 (7H, m,
13
2
ArH); C NMR, δ : 19.98, 20.34, 55.95, 65.32, 125.95, 130.09,
C
32 28
4 6
131.36, 135.06, 139.97, 150.65, 164.04, 165.55, 175.13; MS(FAB):
468 (M+1, 95%), 424, 277, 234, 190, 149 (100%), 105, 55.
Anal. Calcd. for C H N O : C, 64.23; H, 6.25; N, 8.99.
Found: C, 68.38; H, 5.12; N, 9.75.
(4S, 1 5S)-4, 15-Dibenzyl-6, 13-dioxa-23-thia-3, 16, 22-triazatri-
8 , 11
25 29
3 6
c y c l o [ 1 6 . 3 . 1 . 1
2,7,12,17-tetraone (4s).
] t r i c o s a - 1 ( 2 1 ) , 8 , 1 0 , 1 8 ( 2 2 ) , 1 9 - p e n t a e n e -
Found: C, 64.02; H, 6.21; N, 9.06.
(5S, 1 5S)-5, 15-Diisopropyl-3, 17-dioxa-6, 14, 23, 24-tetraazatri-
8,12
cyclo[17.3.1.1 ]tetracosa-1(22),8,10,12(24),19(23),20-hexa-
ene-2,7,13,18-tetraone (4o).
This compound was obtained as white solid 0.15 g, yield 22%;
25
mp: 220-222 ºC; [α]
3400, 3083, 2957, 2926, 1735, 1700, 1676, 1517, 1234, 1093,
= –94.5° (c = 0.1, acetone); IR, ν
:
D
max
-1
745, 701 cm ; H NMR, δ : 3.00-3.40 (4H, m, PhCH ), 4.45
1
This compound was obtained as colorless solid 0.22 g, yield
25
H
(2H, m, CH), 4.38-4.60 (4H, m, CH O), 7.18-7.31 (10H, m,
2
40%; mp: 263-265 ºC; [α]
ν
max:
1515, 1462, 1443, 1380, 1319, 1266, 1235, 1151, 1128, 1084,
= -342.7° (c = 0.30, acetone); IR,
3415, 3097, 3012, 2962, 2935, 2882, 1725, 1675, 1590,
D
2
phenyl-H), 7.80 (2H, d, J = 2.0Hz, thiophene-H), 8.13-8.28 (3H,
m, pyridyl-H), 8.44 (2H, d, J = 7.5Hz, CONH); MS(FAB): 570
(M+1, 60%), 478, 237, 91, 57, 55.
Anal. Calcd. for C H N O S: C, 65.36; H, 4.78; N, 7.38; S,
31 27 3 6
5.63. Found: C, 65.21; H, 4.89; N, 7.65; S, 5.57.
-1 1
1054, 997, 844, 751,692, 646, 567 cm ; H NMR, δ : 0.94-1.04
H
(12H, 2d, J=7.0Hz, CH ), 1.92-1.98 (2H, m, CH), 4.16-4.19 (2H,
3
dd, J=2.7, 11.7Hz, CH O), 4.24-4.29 (2H, m, CH), 5.34-5.36
2
(2H, dd, J=2.0, 11.5Hz, CH O), 8.34-8.36 (2H, d, J=8. 5Hz,
2
( 5 R, 1 4 R) - 5 , 1 4 - D i e t h y l - 3 , 1 6 - d i o x a - 2 3 - t h i a - 6 , 1 3 - d i a z a t r i -
8 , 11
CONH), 8.24-8.43 (6H, m, ArH); MS(FAB): 469 (M+1, 100%),
425, 234, 216, 154, 69, 55.
A n a l. Calcd. for C H N O : C, 61.53; H, 6.02; N, 11.96.
c y c l o [ 1 6 . 3 . 1 . 1
2,7,12,17-tetraone (4t).
] t r i c o s a - 1 ( 2 1 ) , 8 , 1 0 , 1 8 ( 2 2 ) , 1 9 - p e n t a e n e -
24 28
4 6
This compound was obtained as white solid 0.13 g, yield 24%;
25
Found: C, 61.47; H, 6.08; N, 11.87.
mp: >260 ºC; [α]
3083, 2966, 2875, 1729, 1681, 1634, 1544, 1513, 1436, 1387,
= -144.0° (c = 0.1, dmso); IR, ν
3289,
D
max:
(4S, 1 5S)-4,15-Diisopropyl-6,13-dioxa-23-thia-3,16,22-triazatri-
8 , 11
c y c l o [ 1 6 . 3 . 1 . 1
2,7,12,17-tetraone (4p).
] t r i c o s a - 1 ( 2 1 ) , 8 , 1 0 , 1 8 ( 2 2 ) , 1 9 - p e n t a e n e -
-1
1
1299, 1253, 1192, 1142, 1096, 1077, 928, 822, 728 cm ; H
NMR, δ : 0.99-1.05 (6H, t, J=7.5Hz, CH ), 1.74-1.85 (4H, m,
CH ), 4.38-4.40 (4H, m, CH O), 4.51-4.53 (2H, m, CH), 7.70-
H
3
This compound was obtained as white solid 0.10 g, yield
25
2
2
13
18%; mp: 175-178 ºC; [α]
= -82.9° (c = 0.1, dmso); IR, ν
max:
7.71 (2H, d, J=7.8Hz, CONH), 7.62-8.65 (6H, m, ArH);
C
D
3379, 3319, 3083, 2964, 2935, 2880, 1726, 1669, 1585, 1536,
1449, 1371, 1344, 1300, 1244, 1161, 1133, 1097, 98, 973, 839,
NMR, _c: 10.23, 23.37, 52.17, 66.22, 127.94, 129.17, 129.52,
129.68, 130.09, 130.18, 132.98, 133.46, 133.54, 142.87, 160.77,
165.39, 166.23; MS(FAB): 445 (M+1, 4%), 388, 219, 163, 154
(100%), 89, 77; A n a l. Calcd. for C H N O S: C, 59.45; H,
-1
789, 747, 646 cm ; H NMR, δ : 0.91-1.03 (12H, m, CH ),
1
H
1.92-2.04 (2H, m, CH), 3.91-4.73 (6H, m, CH O and CH), 7.44-
3
2
22 24
2 6
8.66 (7H, m, ArH and CONH); MS(FAB): 474 (M+1, 100%),
240, 154, 77, 57.
Anal. Calcd. for C H N O S: C, 58.34; H, 5.75; N, 8.87; S,
5.44; N, 6.30; S, 7.21. Found: C, 59.56; H, 5.51; N, 6.34; S, 7.10.
( 5R, 1 4 R) - 5 , 1 4 - D i e t h y l - 3 , 1 6 - d i o x a - 2 3 - t h i a - 6 , 1 3 , 2 2 - t r i a z a -
8, 11
23 27
3 6
tricyclo[16. 3. 1. 1 ]tricosa-1(21), 8, 10, 18(22), 19-pentaene-
2,7,12,17-tetraone (4u).
6.27. Found: C, 58.61; H, 5.80; N, 8.65; S, 6.04.
( 4 S, 1 6 S) - 4 , 1 6 - D i b e n z y l - 6 , 1 4 - d i o x a - 3 , 1 7 , 2 3 - t r i a z a t r i -
8,12
cyclo[17.3.1.1 ]tetracosa-1(22),8,10,12(24),19(23),20-hexa-
ene-2,7,13,18-tetraone (4q).
This compound was obtained as yellow solid 0.11 g, yield
25
21%; mp: 247-250 ºC; [α]
= -88.3° (c = 0.1,dmso); IR, ν
:
3318, 3078, 2966, 2931, 2875, 1728, 1633, 1546, 1454, 1319,
D
max
-1 1
1243, 1138, 1075, 1039, 991, 835, 751 cm ; H NMR, δ : 0.89-
This compound was obtained as white solid 0.34 g, yield 50%;
25
H
0.94 (6H, m, CH ), 1.62-1.71 (4H, m, CH ), 4.19-4.24 (2H, m,
mp: 239-242 ºC; [α]
= -125.8° (c = 0.1, acetone); IR, ν
3426, 3079, 2952, 2929, 1727, 1668, 1502, 1314, 1119, 751, 697
:
max
D
3
CH), 4.32-4.36 (2H, dd, J=8.0, 11Hz, CH O), 4.46-4.49 (2H, dd,
2
2
J=3.7, 11.2Hz, CH O), 7.64 (2H, s, thiophene-H), 8.08-8.19 (3H,
-1
cm ; H NMR, δ : 2.92-3.18 (4H, m, PhCH ), 4.60 (2H, m,
1
H
CH), 4.25-4.87 (4H, m, CH O), 7.15-7.35 (11H, m, phenyl-H),
2
2
m, pyH), 8.38-8.40 (2H, d, J= 8.5Hz, CONH).
Anal. Calcd. for C H N O S: C, 56.62; H, 5.20; N, 9.43; S,
2
7.77-8.25 (2H, m, phenyl-H), 8.32-8.37 (3H, m, pyridyl-H),
8.88 (2H, d, J = 7.8Hz, CONH), 9.10 (1H, d, J = 1.8Hz, phenyl-
H); MS(FAB): 564 (M+1, 13%), 239, 191, 165, 149, 121, 95, 69
(100%), 57, 55.
Anal. Calcd. for C H N O : C, 70.33; H, 5.19; N, 7.46.
33 29 3 6
Found: C, 70.21; H, 5.22; N, 7.56.
21 23
9.70. Found: C, 56.48; H, 5.27; N, 9.47; S, 9.79.
3 6
(5R, 14 R)-5, 14-Diethyl-3, 16-dioxa-21, 22-dithia-6, 13-diaza-
8,11
tricyclo[16.2.1.1 ]docosa-1(20),8,10,18-tetraene-2,7,12,17-
tetraone (4v).
This compound was obtained as yellow solid 0.097 g, 18%;
25
(5S, 15S)-5, 15-Dibenzyl-3, 17-dioxa-6, 14, 23, 24-tetraazatricy-
8,12
clo[17.3.1.1 ]tetracosa-1(22),8,10,12(24),19(23),20-hexaene-
2,7,13,18-tetraone (4r).
mp: 163-166 ºC; [α] = -76.7° (c = 0.1, dmso); IR, ν : 3418,
34293, 3090, 2966, 2935, 2880, 1713, 1634, 1542, 1458, 1382,
D
max
-1 1
1349, 1253, 1093, 1030, 964, 831, 778, 748, 676 cm ; H NMR,
δ : 0.80-0.945 (6H, m, CH ), 1.50-1.70 (4H, m, CH ), 4.17-4.43
This compound was obtained as white solid 0.19 g, yield 28%;
25
H
(6H, m, CH and CH O), 7.60-7.79 (4H, m, ArH), 8.34-8.40 (2H,
3
2
mp: 272-275 ºC; [α]
= –118.8° (c = 0.1, MeOH); IR, ν
:
3428, 3080, 2952, 2931, 1727, 1669, 1503, 1315, 1120, 751, 698
D
max
2
d, J=8.5Hz, CONH); MS(FAB): 451 (M+1, 5%), 226, 178, 154
(100%), 71, 55.
-1
cm ; H NMR, δ : 2.94-2.99 (4H, m, PhCH ), 4.75 (2H, m,
1
H
2