Mol Divers
Methyl 3-((4-chlorophenyl)carbamoyl)-5-hydroxy-2-
Phenyl 5-hydroxy-2-methyl-3-(phenylcarbamoyl)naphtho
methylnaphtho[1,2-b ]furan-4-carboxylate (12g)
[1,2-b ]furan-4-carboxylate (12j)
◦
◦
Yellow solid; yield 190 mg, 93%; mp 242–243 C; IR
Yellow solid; yield 208 mg, 95%; mp 295–296 C; IR (KBr):
(
1
KBr): 3411, 3318, 2921, 2852, 1652, 1590, 1510, 1446,
229, 1162, 1106, 818, 764, 686 cm ; H NMR (300
3410, 3270, 3057, 2986, 1710, 1663, 1587, 1532, 1497,
−1
1
−1
1438, 1353, 1263, 1195, 1142, 1092, 896, 743, 697 cm
;
1
MHz, DMSO − d6)δ11.59 (s, 1H), 10.57 (s, 1H), 8.35
d, J = 8.1 Hz, 1H), 8.16 (d, J = 8.1 Hz, 1H), 7.85–
.78 (m, 3H), 7.62 (dd, J = 7.8, 7.5 Hz, 1H), 7.43
d, J = 8.7 Hz, 2H), 3.60 (s, 3H), 2.59 (s, 3H);
H NMR (300 MHz, DMSO − d6)δ11.30 (s, 1H), 10.50 (s,
1H), 8.38 (d, J = 8.1 Hz, 1H), 8.18 (d, J = 8.1 Hz, 1H),
7.82 (dd, J = 7.8, 7.5 Hz, 1H), 7.63 (dd, J = 7.8, 7.5
Hz, 1H), 7.55 (d, J = 7.8 Hz, 2H), 7.25–7.14 (m, 7H),
(
7
(
1
3
C
1
3
NMR (75 MHz, DMSO − d6)δ 169.61, 163.14, 156.11,
6.70 (t, J = 7.2 Hz, 1H), 2.62 (s, 3H); C NMR (75
MHz, DMSO−d6)δ 167.84, 162.80, 156.19, 154.91, 149.64,
142.57, 139.13, 130.70, 129.11, 128.45, 126.09, 125.84,
124.54, 123.36, 122.17, 122.0, 119.60, 119.45, 118.21,
1
1
1
54.70, 142.30, 138.39, 130.60, 128.84, 127.13, 125.77,
24.44, 123.23, 121.95, 120.74, 119.53, 118.03, 117.18,
+
00.54, 52.07, 13.13. HR-MS(EI): m/z [M ] calcd. for
+
C22H16ClNO 409.0717; found: 409.0717.
117.44, 115.34, 101.05, 13.36. HR-MS(EI): m/z [M ] calcd.
5
for C27H19NO 437.1263; found: 437.1261.
5
Methyl 3-(benzylcarbamoyl)-5-hydroxy-2-methylnaphtho
Phenyl 5-hydroxy-2-methyl-3-(o -tolylcarbamoyl)naphtho
[1,2-b ]furan-4-carboxylate (12h)
[1,2-b]furan-4-carboxylate (12k)
◦
Yellow solid; yield 165 mg, 85%; mp 185–186 C; IR
◦
Yellow solid; yield 196 mg, 87%; mp 195–196 C; IR (KBr):
(
1
KBr): 3304, 3064, 2924, 2855, 1644, 1534, 1447, 1345,
250, 1168, 1116, 749, 699 cm ; H NMR (300 MHz,
3
1
374, 3056, 2986, 2926, 1710, 1672, 1599, 1431, 1357, 1265,
191, 1146, 1100, 895, 833, 739, 600 cm ; H NMR (300
−1 1
−1
1
CDCl3 + DMSO − d6)δ 11.79 (s, 1H), 8.18 (d, J = 8.4 Hz,
H), 8.08 (brs, 1H), 7.89 (d, J = 8.1 Hz, 1H), 7.53
dd, J = 7.8, 7.2 Hz, 1H), 7.38–7.16 (m, 6H), 4.48, (d,
J = 6.0 Hz, 2H), 3.60 (s, 3H), 2.36 (s, 3H); C NMR
MHz, DMSO − d6)δ11.14 (s, 1H), 9.77 (s, 1H), 8.44 (d,
J = 8.4 Hz, 1H), 8.23 (d, J = 8.1 Hz, 1H), 7.83 (t, J = 7.5
Hz, 1H), 7.65 (dd, J = 7.8, 7.2 Hz, 1H), 7.34–7.25 (m, 5H),
1
(
1
3
7
.21–7.13 (m, 2H), 7.04 (dd, J = 7.2, 6.6 Hz, 1H), 6.96 (dd,
(
1
75 MHz, CDCl3 + DMSO − d6)δ 170.37, 165.10, 157.53,
13
J = 7.5, 6.9Hz, 1H), 2.73(s, 3H), 2.17(s, 3H); CNMR(75
53.59, 142.31, 138.48, 129.49, 128.02, 127.45, 126.73,
MHz, DMSO−d6)δ 167.40, 162.54, 155.25, 154.42, 149.80,
1
9
24.54, 124.04, 123.39, 121.57, 119.03, 117.31, 116.41,
8.85, 50.86, 42.93, 12.66. HR-MS(EI): m/z [M ] calcd.
1
1
1
42.48, 135.81, 131.35, 130.12, 129.89, 128.84, 125.81,
+
25.40, 125.22, 124.94, 124.83, 124.25, 123.05, 122.10,
21.92, 119.27, 118.47, 116.94, 101.54, 17.67, 13.28. HR-
MS(EI): m/z [M ] calcd. for C28H21NO 451.1420; found:
for C23H19NO 389.1263; found: 389.1262.
5
+
5
451.1417.
Methyl 5-hydroxy-2-phenyl-3-(phenylcarbamoyl)naphtho
[1,2-b ]furan-4-carboxylate (12i)
Phenyl 5-hydroxy-2-methyl-3-(p -tolylcarbamoyl)naphtho
◦
[1,2-b]furan-4-carboxylate (12l)
Yellow solid; yield 179 mg, 82%; mp 241–242 C; IR (KBr):
3
411, 2925, 1658, 1599, 1538, 1444, 1349, 1251, 1156, 1110,
◦
Yellow solid; yield 210 mg, 93%; mp 243–244 C; IR (KBr):
−1
1
7
62, 688 cm ; H NMR (300 MHz, DMSO − d6)δ12.02
3
371, 3285, 2925, 1651, 1598, 1515, 1261, 1187, 1145, 1096,
(
brs, 1H), 10.63 (s, 1H), 8.41 (d, J = 8.4 Hz, 2H), 7.99
−1 1
7
42, 700 cm ; H NMR (300 MHz, DMSO − d6)δ11.24
(
d, J = 7.2 Hz, 2H), 7.89 (t, J = 7.5 Hz, 1H), 7.77 (d,
(
brs, 1H), 10.22 (s, 1H), 8.41 (d, J = 8.1 Hz, 1H), 8.21 (d,
J = 7.8 Hz, 2H), 7.70 (dd, J = 8.1, 7.2 Hz, 1H), 7.52 (dd,
J = 7.8, 7.2 Hz, 2H), 7.46 (d, J = 7.2 Hz, 1H), 7.38 (t,
J = 7.8 Hz, 2H), 7.12 (dd, J = 7.5, 7.2 Hz, 1H), 3.61 (s,
J = 8.1 Hz, 1H), 7.83 (dd, J = 7.8, 7.2 Hz, 1H), 7.63 (dd,
J = 7.8, 7.5 Hz, 1H), 7.41 (d, J = 7.8 Hz, 2H), 7.26–7.16
(m, 5H), 7.00 (d, J = 8.1 Hz, 2H), 2.63 (s, 3H), 2.24 (s, 3H);
1
3
3
1
1
1
H); C NMR (75 MHz, DMSO − d6)δ 169.90, 163.36,
57.23, 152.09, 142.82, 139.42, 130.96, 129.42, 129.32,
29.12, 129.02, 126.51, 126.13, 124.58, 123.74, 123.40,
1
3
C NMR (75 MHz, DMSO − d6)δ 167.53, 162.19, 155.84,
54.46, 149.47, 142.34, 136.33, 131.95, 130.24, 128.70,
28.42, 125.62, 125.40, 124.21, 123.13, 121.94, 121.64 (4
1
1
22.62, 120.13, 119.19, 118.69, 116.92, 100.16, 52.20. HR-
+
Ar-C), 119.37, 119.24, 115.06, 100.97, 20.13, 12.92. HR-
MS(EI): m/z [M ] calcd. for C27H19NO 437.1263; found:
5
+
MS(EI): m/z [M ] calcd. for C28H21NO 451.1420; found:
5
437.1266.
4
51.1422.
1
23