2708
D. TAHMASSEBI, J. A. BRYSON, AND S. I. BINZ
ꢁ
1 1
Compound 4l. IR: 3326, 3189, 2959, 2195, 1681, 1631, 1604, 1368 cm ; H
NMR (DMSO-d ): d (ppm) ¼ 0.92 (3H, s, Me), 1.01 (3H, s, Me), 2.06 (1H, d,
6
0
J ¼ 16 Hz, H-6), 2.22 (1H, d, J ¼ 16 Hz, H-6 ), 2.39 (1H, d, J ¼ 18 Hz, H-8), 2.50
0
(
(
(
(
1H, d, J ¼ 18 Hz, H-8 ), 4.04 (1H, s, H-4), 6.63 (2H, d, J ¼ 7.5 Hz, H-Ar), 6.89
1
3
2H, br s, NH ), 6.91 (2H, d, J ¼ 7.5 Hz, H-Ar), 9.22 (1H, s, OH); C NMR
2
DMSO-d ): d (ppm) ¼ 27.47 (Me), 29.08 (Me), 32.46 (C-7), 35.39 (C-4), 40.39
6
C-8), 50.75 (C-6), 59.51 (C-3), 113.90 (C-4a), 120.54 (CN), 115.68, 128.82, 133.85,
56.66 (C-Ar), 159.09 (C-2), 162.65 (C-8a), 196.31 (C-5).
1
ꢁ
1
;
Compound 4m. IR: 3396, 3281, 3027, 2956, 1689, 1652, 1608, 1522, 1369 cm
1
H NMR (CDCl ): d (ppm) ¼ 0.97 (3H, s, Me), 1.09 (3H, s, Me), 1.15 (3H, t, J ¼ 7 Hz,
3
0
Et), 2.14 (1H, d, J ¼ 16.3 Hz, H-6), 2.24 (1H, d, J ¼ 16.3 Hz, H-6 ), 2.42 (2H, br s, H-8),
4
.02 (2H, q, J ¼ 7 Hz, Et), 4.69 (1H, s, H-4), 6.15 (2H, br s, NH ), 7.05–7.28 (5H, m,
3 3 2
2
1
3
H-Ar); C NMR (CDCl ): d (ppm) ¼ 14.21 (CH CH ), 27.44 (Me), 29.11 (Me), 32.27
(
(
(
C-7), 33.83 (C-4), 40.67 (C-8), 50.73 (C-6), 59.69 (CH CH ), 80.89 (C-3), 116.85
3 2
C-4a), 126.04, 127.04, 128.26, 145.80 (C-Ar), 158.31 (C-2), 161.34 (C-8a), 169.16
CO ), 196.41 (C-5).
2
ꢁ
1 1
Compound 4n. IR: 3411, 3300, 2957, 1690, 1652, 1608, 1360 cm ; H NMR
(
(
(
CDCl ): d (ppm) ¼ 0.97 (3H, s, Me), 1.07 (3H, s, Me), 1.11 (3H, t, J ¼ 7 Hz, Et), 2.11
3
0
1H, d, J ¼ 16.3 Hz, H-6), 2.21 (1H, d, J ¼ 16.3 Hz, H-6 ), 2.39 (2H, br s, H-8), 3.99
2H, q, J ¼ 7 Hz, Et), 4.99 (1H, s, H-4), 6.25 (2H, br s, NH ), 6.98–7.31 (4H, m,
2
1
3
H-Ar); C NMR (CDCl ): d (ppm) ¼ 14.19 (CH CH ), 27.43 (Me), 29.07 (Me),
3
3
2
3
1
1
2.07 (C-7), 33.05 (C-4), 40.63 (C-8), 50.69 (C-6), 59.67 (CH CH ), 79.10 (C-3),
3 2
14.85 (C-4a), 126.04, 127.32, 129.80, 132.34, 133.58, 141.91 (C-Ar), 158.53 (C-2),
61.83 (C-8a), 169.17 (CO ), 196.40 (C-5).
2
ꢁ
1 1
Compound 4o. IR: 3476, 3323, 2976, 1686, 1655, 1522, 1359, 1203 cm ; H
NMR (CDCl ): d (ppm) ¼ 0.95 (3H, s, Me), 1.08 (3H, s, Me), 1.14 (3H, t, J ¼ 7 Hz,
3
0
Et), 2.13 (1H, d, J ¼ 16.3 Hz, H-6), 2.23 (1H, d, J ¼ 16.3 Hz, H-6 ), 2.40 (2H, br s,
H-8), 4.02 (2H, q, J ¼ 7 Hz, Et), 4.65 (1H, s, H-4), 6.20 (2H, br s, NH ), 7.12–7.22
2
1
3
(
(
(
(
4H, m, H-Ar); C NMR (CDCl ): d (ppm) ¼ 14.22 (CH CH ), 27.34 (Me), 29.10
3 2
3
3
2
Me), 32.23 (C-7), 33.45 (C-4), 40.62 (C-8), 50.74 (C-6), 59.74 (CH CH ), 80.27
C-3), 116.36 (C-4a), 127.89, 129.66, 131.60, 144.43 (C-Ar), 158.31 (C-2), 161.49
C-8a), 168.93 (CO ), 196.38 (C-5).
2
ꢁ
1 1
Compound 4p. IR: 3437, 3297, 2954, 1689, 1667, 1622, 1517, 1342 cm ; H
NMR (CDCl ): d (ppm) ¼ 0.98 (3H, s, Me), 1.12 (3H, s, Me), 1.15 (3H, t, J ¼ 7 Hz,
3
0
Et), 2.15 (1H, d, J ¼ 16 Hz, H-6), 2.27 (1H, d, J ¼ 16 Hz, H-6 ), 2.48 (2H, br s, H-8),
4
.03 (2H, q, J ¼ 7 Hz, Et), 4.80 (1H, s, H-4), 6.31 (2H, br s, NH ), 7.38 (1H, t,
2
J ¼ 8 Hz, H-Ar), 7.62 (1H, d, J ¼ 8 Hz, H-Ar), 7.99 (1H, d, J ¼ 8 Hz, H-Ar), 8.11
1
3
(
(
(
(
1H, s, H-Ar); C NMR (CDCl ): d (ppm) ¼ 14.21 (CH CH ), 27.38 (Me), 29.07
3
3
2
Me), 32.30 (C-7), 34.21 (C-4), 40.64 (C-8), 50.62 (C-6), 59.88 (CH CH ), 79.55
3
2
C-3), 115.59 (C-4a), 121.33, 123.17, 128.50, 134.88, 148.19, 148.42 (C-Ar), 158.63
C-2), 162.38 (C-8a), 168.85 (CO ), 196.59 (C-5).
2
ꢁ
1 1
Compound 4q. IR: 3471, 3335, 2996, 1685, 1654, 1508, 1341, 1204 cm ; H
NMR (CDCl ): d (ppm) ¼ 0.93 (3H, s, Me), 1.07 (3H, s, Me), 1.11 (3H, t, J ¼ 7 Hz,
3
0
Et), 2.11 (1H, d, J ¼ 16.3 Hz, H-6), 2.23 (1H, d, J ¼ 16.3 Hz, H-6 ), 2.43 (2H, br s,