5
1
1
12.1, 101.9; IR (KBr): 3441, 2924, 1733, 1692, 1625, 1528, 1455,
346, 1157, 758 cm ; HRMS (ESI): m/z [M + Na] calcd for
Hz, 1H), 7.57–7.47 (m, 4H), 7.44 (d, J = 7.8 Hz, 1H), 7.35 (s, 1H),
–1
+
13
6.97 (d, J = 7.8 Hz, 1H), 6.90 (t, J = 7.2 Hz, 1H); C NMR (CDCl3,
C H NNaO : 506.0483; found: 506.0480.
150 MHz): 193.9, 183.4, 163.3, 162.8, 156.5, 155.8, 153.9, 151.6,
δ
26
13
9
4
.3.8
3-(2-hydroxybenzoyl)-4-(3-nitrobenzoyl)pyrano[3,2-
140.1, 138.1, 136.0, 135.1, 132.6, 127.2, 126.6, 125.7, 124.2, 122.6,
119.5, 119.1, 118.4, 117.6, 112.4, 101.9; IR (KBr): 3439, 3111, 1751,
c]chromene-2,5-dione (3h). Yield: 66%, 95.7 mg; Yellow solid; m.p.
o
1
–1
1
1
1
1
24-125 C; H NMR (CDCl , 600 MHz):
H), 8.46 (d, J = 7.8 Hz, 1H), 8.28–8.18 (m, 2H), 7.82 (t, J = 7.8 Hz,
H), 7.71 (t, J = 7.8 Hz, 1H), 7.58–7.51 (m, 3H), 7.44 (d, J = 8.4 Hz,
δ
10.96 (s, 1H), 8.62 (s,
1727, 1659, 1624, 1540, 1197, 756 cm ; HRMS (ESI): m/z [M +
3
+
Na] calcd for C H NaO S: 467.0196; found: 467.0197.
24
12
7
13
H), 6.98 (d, J = 7.8 Hz, 1H), 6.93 (t, J = 7.2 Hz, 1H); C NMR
4.3.14
4-(benzofuran-2-carbonyl)-3-(2-
(
1
1
CDCl , 150 MHz):
54.0, 151.8, 148.3, 138.4, 136.7, 136.5, 134.1, 132.4, 130.2, 128.4,
26.0, 124.4, 124.0, 123.7, 119.6, 118.9, 118.6, 117.7, 112.4, 102.0;
δ
193.7, 188.7, 163.7, 162.8, 156.9, 155.4,
hydroxybenzoyl)pyrano[3,2-c]chromene-2,5-dione (3n). Yield:
3
o
1
73%, 104.7 mg; Yellow solid; m.p. 226-228 C; H NMR (CDCl
,
3
600 MHz): 11.12 (s, 1H), 8.20 (d, J = 7.8 Hz, 1H), 7.80 (t, J = 7.8
δ
IR (KBr): 3444, 2922, 1733, 1692, 1625, 1535, 1456, 1350, 1226,
Hz, 1H), 7.70 (d, J = 7.8 Hz, 1H), 7.60 (s, 1H), 7.56 (d, J = 7.8 Hz,
1H), 7.52 (t, J = 7.8 Hz, 1H), 7.49–7.43 (m, 4H), 7.33–7.29 (m, 1H),
6.95 (d, J = 8.4 Hz, 1H), 6.82 (t, J = 7.2 Hz, 1H); C NMR (CDCl3,
–1
+
1157, 758 cm ; HRMS (ESI): m/z [M + Na] calcd for
13
C H NNaO : 506.0483; found: 506.0480.
26
13
9
1
50 MHz): 193.7, 179.6, 163.1, 162.8, 156.9, 156.0, 155.8, 153.9,
δ
4
.3.9
4-(4-chlorobenzoyl)-3-(2-hydroxybenzoyl)pyrano[3,2-
151.3, 150.9, 138.1, 136.1, 132.4, 129.0, 126.8, 125.8, 124.3, 124.2,
123.9, 123.8, 119.3, 119.1, 118.4, 117.6, 114.7, 112.5, 112.4, 102.3;
IR (KBr): 3439, 1768, 1728, 1667, 1608, 1531, 1454, 1252, 756 cm ;
HRMS (ESI): m/z [M + Na] calcd for C H NaO : 501.0581; found:
501.0571.
c]chromene-2,5-dione (3i). Yield: 90%, 127.6 mg; Yellow solid; m.p.
2
=
o
1
–1
51-253 C; H NMR (CDCl , 600 MHz):
8.4 Hz, 1H), 7.83–7.76 (m, 3H), 7.55–7.49 (m, 3H), 7.44 (t, J = 7.8
δ
11.04 (s, 1H), 8.19 (d, J
3
+
28
14
8
13
Hz, 3H), 6.97 (d, J = 7.8 Hz, 1H), 6.91 (t, J = 7.8 Hz, 1H); C NMR
DMSO-d , 150 MHz): 190.3, 189.6, 162.6, 159.0, 157.3, 156.7,
53.3, 149.1, 138.9, 136.2, 135.8, 134.8, 130.8, 130.5, 128.9, 126.8,
25.8, 123.9, 123.0, 119.5, 117.3, 116.5, 112.8, 102.7; IR (KBr):
(
δ
6
1
1
3
4.3.15
4-(1-naphthoyl)-3-(2-hydroxybenzoyl)pyrano[3,2-
c]chromene-2,5-dione (3o). Yield: 55%, 80.5 mg; Yellow solid; m.p.
241-243 C; H NMR (CDCl , 600 MHz): δ 11.01 (s, 1H), 8.94 (d, J
= 7.8 Hz, 1H), 8.19 (d, J = 7.8 Hz, 1H), 8.04 (d, J = 7.8 Hz, 1H),
7.93–7.84 (m, 2H), 7.76 (t, J = 7.8 Hz, 1H), 7.66–7.55 (m, 3H), 7.49
–1
o
1
443, 1752, 1730, 1672, 1626, 1540, 1456, 1244, 761 cm ; HRMS
3
+
(ESI): m/z [M + Na] calcd for C H ClNaO : 495.0242; found:
26
13
7
4
95.0245.
(
t, J = 7.2 Hz, 2H), 7.45 (t, J = 7.8 Hz, 1H), 7.39 (d, J = 8.4 Hz, 1H),
13
4
.3.10
4-(3-chlorobenzoyl)-3-(2-hydroxybenzoyl)pyrano[3,2-
6.92 (t, J = 7.2 Hz, 1H), 6.89 (d, J = 8.4 Hz, 1H); C NMR (CDCl
3
,
c]chromene-2,5-dione (3j). Yield: 80%, 113.5 mg; Yellow solid; m.p.
150 MHz): 194.3, 191.3, 163.2, 162.7, 156.8, 156.0, 153.9, 152.6,
δ
o
1
2
=
7
36-238 C; H NMR (CDCl , 600 MHz):
δ
11.04 (s, 1H), 8.18 (d, J
7.2 Hz, 1H), 7.85–7.75 (m, 2H), 7.73 (d, J = 7.2 Hz, 1H), 7.59–
.48 (m, 4H), 7.45–7.38 (m, 2H), 6.97 (d, J = 8.4 Hz, 1H), 6.91 (t, J
138.0, 135.9, 135.5, 133.8, 132.9, 132.6, 131.1, 130.6, 129.2, 128.4,
127.0, 125.9, 125.7, 124.2, 123.9, 122.6, 119.5, 119.2, 118.3, 117.6,
112.5, 102.2; IR (KBr): 3442, 2923, 1756, 1731, 1652, 1623, 1537,
3
13
–1
+
=
7.2 Hz, 1H); C NMR (CDCl , 150 MHz):
δ
193.8, 189.2, 163.3,
1455, 1197, 768, 755 cm ; HRMS (ESI): m/z [M + Na] calcd for
3
1
1
1
62.7, 156.7, 155.6, 154.0, 152.0, 138.2, 136.7, 136.2, 135.1, 134.3,
32.4, 130.1, 128.7, 127.1, 125.8, 124.3, 123.4, 119.5, 119.0, 118.4,
17.6, 112.4, 102.1; IR (KBr): 3445, 1734, 1677, 1629, 1517, 1428,
C
30
H
16NaO
7
: 511.0788; found: 511.0788.
4.3.16
4-(2-naphthoyl)-3-(2-hydroxybenzoyl)pyrano[3,2-
–1
+
1160, 762 cm ; HRMS (ESI): m/z [M + Na] calcd for
c]chromene-2,5-dione (3p). Yield: 58%, 84.9 mg; Yellow solid; m.p.
185-187 C; H NMR (CDCl
o
1
C H ClNaO : 495.0242; found: 495.0242.
, 600 MHz): δ 11.02 (s, 1H), 8.30 (s,
3
26
13
7
1
H), 8.12 (d, J = 7.8 Hz, 1H), 7.94 (d, J = 8.4 Hz, 1H), 7.89–7.81 (m,
4
.3.11
4-(4-bromobenzoyl)-3-(2-hydroxybenzoyl)pyrano[3,2-
3H), 7.70 (t, J = 6.6 Hz, 1H), 7.61 (d, J = 7.8 Hz, 1H), 7.58 (t, J =
c]chromene-2,5-dione (3k). Yield: 87%, 134.9 mg; Yellow solid;
7.2 Hz, 1H), 7.49 (t, J = 7.2 Hz, 1H), 7.47–7.40 (m, 2H), 7.34 (d, J =
o
1
13
m.p. 214-216 C; H NMR (CDCl , 600 MHz):
δ
11.03 (s, 1H), 8.17
8.4 Hz, 1H), 6.92–6.85 (m, 2H); C NMR (CDCl , 150 MHz):
δ
3
3
(
d, J = 7.8 Hz, 1H), 7.78 (t, J = 7.8 Hz, 1H), 7.71 (d, J = 7.2 Hz, 2H),
194.0, 190.2, 163.2, 162.6, 156.5, 155.8, 153.9, 152.5, 138.0, 136.1,
135.9, 132.5, 132.1, 131.8, 129.7, 129.2, 128.9, 127.9, 126.9, 125.6,
124.1, 123.5, 123.0, 119.4, 119.1, 118.3, 117.5, 112.4, 109.9, 102.3;
7
6
1
1
1
1
.60 (d, J = 8.4 Hz, 2H), 7.56–7.46 (m, 3H), 7.42 (d, J = 8.4 Hz, 1H),
13
.97 (d, J = 8.4 Hz, 1H), 6.91 (t, J = 7.2 Hz, 1H); C NMR (CDCl3,
–
1
50 MHz): 193.9, 189.5, 163.3, 162.8, 156.6, 155.6, 153.9, 152.1,
δ
IR (KBr): 3443, 1733, 1674, 1624, 1536, 1455, 1246, 755 cm ;
+
38.2, 136.2, 134.0, 132.5, 132.2, 130.3, 129.9, 125.8, 124.2, 123.3,
19.5, 119.0, 118.4, 117.6, 112.4, 102.1; IR (KBr): 3443, 2924, 1753,
HRMS (ESI): m/z [M + Na] calcd for C30
511.0787.
H16NaO : 511.0788; found:
7
–1
730, 1671, 1626, 1540, 1456, 1244, 807 cm ; HRMS (ESI): m/z
+
[
M + Na] calcd for C H BrNaO : 538.9737; found: 538.9735.
4.3.17
4-benzoyl-3-(2-hydroxy-5-methylbenzoyl)-9-
26
13
7
methylpyrano[3,2-c]chromene-2,5-dione (3q). Yield: 68%, 95.1
o
1
4
.3.12
3-(2-hydroxybenzoyl)-4-(thiophene-2-
mg; Yellow solid; m.p. 254-255 C; H NMR (CDCl , 600 MHz): δ
3
carbonyl)pyrano[3,2-c]chromene-2,5-dione (3l). Yield: 75%, 99.9
10.94 (s, 1H), 7.99 (s, 1H), 7.84 (d, J = 7.8 Hz, 2H), 7.62–7.56 (m,
2H), 7.46 (t, J = 7.8 Hz, 2H), 7.33–7.28 (m, 3H), 6.86 (d, J = 8.4 Hz,
o
1
mg; Yellow solid; m.p. 242-244 C; H NMR (CDCl , 600 MHz):
δ
3
13
1
=
=
1.14 (s, 1H), 8.18 (d, J = 8.4 Hz, 1H), 7.83–7.74 (m, 2H), 7.60 (d, J
1H), 2.51 (s, 3H), 2.26 (s, 3H); C NMR (CDCl , 150 MHz): δ
3
3.0 Hz, 1H), 7.57–7.49 (m, 3H), 7.44 (d, J = 8.4 Hz, 1H), 7.11 (t, J
193.9, 190.4, 163.1, 160.8, 156.8, 155.9, 152.4, 152.2, 139.4, 137.2,
135.9, 135.1, 134.4, 131.9, 129.0, 128.8, 128.7, 123.7, 123.0, 118.8,
118.1, 117.3, 112.1, 102.2, 20.9, 20.4; IR (KBr): 3435, 2922, 1758,
13
4.2 Hz, 1H), 6.97 (d, J = 8.4 Hz, 1H), 6.90 (t, J = 7.8 Hz, 1H);
193.7, 181.6, 163.3, 162.8, 156.4, 155.7,
54.0, 150.6, 141.6, 138.2, 136.4, 136.1, 135.1, 132.6, 128.4, 125.7,
24.2, 122.9, 119.5, 119.1, 118.4, 117.6, 112.4, 101.9; IR (KBr):
C
NMR (CDCl , 150 MHz):
δ
3
–1
1
1
3
1723, 1672, 1629, 1546, 1482, 1183, 788 cm ; HRMS (ESI): m/z
+
[M + Na] calcd for C28H18NaO : 489.0945; found: 489.0948.
7
–1
445, 2924, 1738, 1650, 1625, 1538, 1408, 1243, 755 cm ; HRMS
+
(ESI): m/z [M + Na] calcd for C H NaO S: 467.0196; found:
4.3.18
4-benzoyl-3-(2-hydroxy-4-methoxybenzoyl)-8-
24
12
7
4
67.0199.
methoxypyrano[3,2-c]chromene-2,5-dione (3r). Yield: 85%, 127.0
o
1
mg; Yellow solid; m.p. 241-242 C; H NMR (CDCl , 600 MHz):
δ
3
4
.3.13
3-(2-hydroxybenzoyl)-4-(thiophene-3-
11.63 (s, 1H), 7.97 (d, J = 9.0 Hz, 1H), 7.83 (d, J = 7.8 Hz, 2H), 7.55
(t, J = 7.2 Hz, 1H), 7.47–7.37 (m, 3H), 7.01–6.94 (m, 1H), 6.79 (s,
1H), 6.39 (d, J = 9.0 Hz, 1H), 6.32 (s, 1H), 3.86 (s, 3H), 3.78 (s, 3H);
carbonyl)pyrano[3,2-c]chromene-2,5-dione (3m). Yield: 71%, 94.6
mg; Yellow solid; m.p. 231-232 C; H NMR (CDCl , 600 MHz):
1
o
1
δ
3
13
1.14 (s, 1H), 8.18 (d, J = 7.8 Hz, 1H), 8.01 (s, 1H), 7.79 (t, J = 7.2
C NMR (CDCl , 150 MHz): δ 191.6, 190.6, 167.2, 166.1, 165.7,
3