(4H, br, 4OH), 4.62 (1H, d, J = 5.6, H-4), 5.06 (1H, d, J = 5.6, H-3), 5.24 (1H, d, J = 8.0, H-1), 6.89 (2H, d, J = 8.0, ArH), 7.12
(2H, d, J = 8.0, ArH), 7.44 (2H, d, J = 8.4, ArH), 7.53 (2H, d, J = 8.4, ArH), 8.69 (1H, s, NH).
+
HR-MS-ESI m/z calcd for C H ClNNaO [M + Na] 536.1452, found 536.1450.
27 28
7
2-(4-Bromophenyl)-4-(4-ꢀ-D-allopyranosyloxyphenyl)-5-oxo-4,6,7,8-tetrahydroquinoline (4e). This compound
was prepared from 2e, cyclohexane-1,3-dione, and ammonium acetate; yield 81%, yellow powder, mp 152–154ꢁC.
–1
1
IR (KBr, ꢃ, cm ): 3361, 2953, 2926, 2887, 1654, 1594, 1485, 1444, 1391, 1078, 828, 619. H NMR (400 MHz,
DMSO-d , ꢄ, ppm, J/Hz): 1.03–1.07 (2H, m, H-7), 1.81–1.90 (2H, m, H-8), 2.50–2.65 (2H, m, H-6), 3.36–3.91 (6H, m), 4.52
6
(1H, d, J = 5.6, H-4), 4.59–5.12 (4H, br, 4OH), 5.04 (1H, d, J = 5.6, H-3), 5.25 (1H, d, J = 8.0, H-1), 6.88 (2H, d, J = 8.0, ArH),
7.11 (2H, d, J = 8.0, ArH), 7.45 (2H, d, J = 8.4, ArH), 7.57 (2H, d, J = 8.4, ArH), 8.71 (1H, s, NH).
+
HR-MS-ESI m/z calcd for C H BrNNaO [M + Na] 580.0947, found 580.0963.
27 28
7
7,7-Dimethyl-2-phenyl-4-(4-ꢀ-D-allopyranosyloxyphenyl)-5-oxo-4,6,7,8-tetrahydroquinoline (4f). This compound
was prepared from 2a, 5,5-dimethylcylohexane-1,3-dione, and ammonium acetate; yield 83%, yellow powder, mp 172–174ꢁC.
–1
1
IR (KBr, ꢃ, cm ): 3416, 2925, 2865, 1744, 1599, 1652, 1485, 1388, 1116, 1094, 835, 618. H NMR (400 MHz,
DMSO-d , ꢄ, ppm, J/Hz): 0.94 (3H, s, CH ), 1.03 (3H, s, CH ), 1.98 (1H, d, J = 16.0, H-8), 2.16 (1H, d, J = 16.0, H-8), 2.46
6
3
3
(2H, s, H-6), 3.34–3.90 (6H, m), 4.50 (1H, d, J = 5.6, H-4), 4.59–5.10 (4H, br, 4OH), 5.05 (1H, d, J = 5.6, H-3), 5.20 (1H, d,
J = 8.0, H-1), 6.89 (2H, d, J = 8.0, ArH), 7.13 (2H, d, J = 8.0, ArH), 7.35–7.40 (3H, m, ArH), 7.49 (2H, d, J = 8.4, ArH), 8.60
(1H, s, NH).
+
HR-MS-ESI m/z calcd for C H NNaO [M + Na] 530.2155, found 530.2021.
29 33
7
7,7-Dimethyl-2-(4-methylphenyl)-4-(4-ꢀ-D-allopyranosyloxyphenyl)-5-oxo-4,6,7,8-tetrahydroquinoline (4g).
This compound was prepared from 2b, 5,5-dimethyl-cylohexane-1,3-dione, and ammonium acetate; yield 84%, yellow powder,
mp 139–141ꢁC.
–1
1
IR (KBr, ꢃ, cm ): 3362, 2925, 2882, 1660, 1592, 1485, 1390, 1227, 1085, 830, 619. H NMR (400 MHz, DMSO-d ,
6
ꢄ, ppm, J/Hz): 0.93 (3H, s, CH ), 1.07 (3H, s, CH ), 1.99 (1H, d, J = 16.0, H-8), 2.14 (1H, d, J = 16.0, H-8), 2.24 (3H, s, CH ),
3
3
3
2.48 (2H, s, H-6), 3.42–3.47 (6H, m), 4.51 (1H, d, J = 5.6, H-4), 4.59–5.10 (4H, br, 4OH), 5.06 (1H, d, J = 5.6, H-3), 5.19 (1H,
d, J = 8.0, H-1), 6.89 (2H, d, J = 8.0, ArH), 7.12 (2H, d, J = 8.0, ArH), 7.38 (2H, d, J = 8.4, ArH), 7.50 (2H, d, J = 8.4, ArH),
8.61 (1H, s, NH).
+
HR-MS-ESI m/z calcd for C H NNaO [M + Na] 544.2311, found 544.2307.
30 35
7
7,7-Dimethyl-2-(4-fluorophenyl)-4-(4-ꢀ-D-allopyranosyloxyphenyl)-5-oxo-4,6,7,8-tetrahydroquinoline (4h). This
compound was prepared from 2c, 5,5-dimethyl-cyclohexane-1,3-dione, and ammonium acetate; yield 76%, yellow powder,
mp 163–165ꢁC.
–1
1
IR (KBr, ꢃ, cm ): 3352, 2925, 2882, 1661, 1595, 1485, 1390, 1228, 914, 839, 620. H NMR (400 MHz, DMSO-d ,
6
ꢄ, ppm, J/Hz): 0.96 (3H, s, CH ), 1.05 (3H, s, CH ), 1.92 (1H, d, J = 16.0, H-8), 2.15 (1H, d, J = 16.0, H-8), 2.48 (2H, s, H-6),
3
3
3.34–3.90 (6H, m), 4.49 (1H, d, J = 5.6, H-4), 4.58–5.09 (4H, br, 4OH), 5.03 (1H, d, J = 5.6, H-3), 5.16 (1H, d, J = 8.0, H-1),
6.90 (2H, d, J = 8.0, ArH), 7.12 (2H, d, J = 8.0, ArH), 7.22 (2H, d, J = 8.4, ArH), 7.52 (2H, d, J = 8.4, ArH), 8.60 (1H, s, NH).
–
HR-MS-ESI m/z calcd for C H FO [M – H] 524.2085, found 524.2101.
29 31
7
7,7-Dimethyl-2-(4-chlorophenyl)-4-(4-ꢀ-D-allopyranosyloxyphenyl)-5-oxo-4,6,7,8-tetrahydroquinoline (4i). This
compound was prepared from 2d, 5,5-dimethyl-cyclohexane-1,3-dione, and ammonium acetate; yield 79%, yellow powder,
mp 142–143ꢁC.
–1
1
IR (KBr, ꢃ, cm ): 3361, 2953, 2826, 1660, 1597, 1490, 1390, 1230, 1038, 838, 620. H NMR (400 MHz, DMSO-d ,
6
ꢄ, ppm, J/Hz): 0.93 (3H, s, CH ), 1.06 (3H, s, CH ), 2.00 (1H, d, J = 16.0, H-8), 2.16 (1H, d, J = 16.0, H-8), 2.49 (2H, s, H-6),
3
3
3.35–3.90 (6H, m), 4.47–5.02 (4H, br, 4OH), 4.55 (1H, d, J = 5.6, H-4), 5.05 (1H, d, J = 5.6, H-3), 5.23 (1H, d, J = 8.0, H-1),
6.88 (2H, d, J = 8.0, ArH), 7.11 (2H, d, J = 8.0, ArH), 7.44 (2H, d, J = 8.4, ArH), 7.52 (2H, d, J = 8.4, ArH), 8.62 (1H, s, NH).
–
HR-MS-ESI m/z calcd for C H ClNO [M – H] 540.1789, found 540.1790.
29 31
7
7,7-Dimethyl-2-(4-bromophenyl)-4-(4-ꢀ-D-allopyranosyloxyphenyl)-5-oxo-4,6,7,8-tetrahydroquinoline (4j). This
compound was prepared from 2e, 5,5-dimethyl-cyclohexane-1,3-dione, and ammonium acetate; yield 77%, yellow powder,
mp 163–165ꢁC.
–1
1
IR (KBr, ꢃ, cm ): 3353, 2927, 2871, 1670, 1589, 1485, 1393, 1228, 1035, 825, 618. H NMR (400 MHz, DMSO-d ,
6
ꢄ, ppm, J/Hz): 0.95 (3H, s, CH ), 1.06 (3H, s, CH ), 2.07 (1H, d, J = 16.0, H-8), 2.16 (1H, d, J = 16.0, H-8), 2.47 (2H, s, H-6),
3
3
3.35–3.90 (6H, m), 4.51 (1H, d, J = 5.6, H-4), 4.59–5.10 (4H, br, 4OH), 5.05 (1H, d, J = 5.6, H-3), 5.24 (1H, d, J = 8.0, H-1),
6.89 (2H, d, J = 8.0, ArH), 7.11 (2H, d, J = 8.0, ArH), 7.45 (2H, d, J = 8.4, ArH), 7.58 (2H, d, J = 8.4, ArH), 8.63 (1H, s, NH).
+
HR-MS-ESI m/z calcd for C H BrNNaO [M + Na] 608.1260, found 608.1258.
29 32
7
913