1248
L. Q. Wu, W. L. Li, and F. L. Yan
Vol 47
[M þ H]þ. Anal. calcd for C27H18O2: C, 86.61; H, 4.85.
found: C, 86.49; H, 4.92.
General procedure for the preparation of 4. To a mixture
of b-naphthol (1 mmol), aldehyde (1 mmol) and 2H-indene-
1,3-dione (1 mmol), SA (0.03 mmol) was added. The mixture
was stirred (use a high power electric mixer) at 120ꢀC for an
appropriate time (Table 3). After completion of the reaction
(TLC), the reaction mixture was treated with water (10 mL)
and extracted with CH2Cl2 (2 ꢁ 10 mL), filtered and the sol-
vent evaporated in vacuo. Products were puried by silica gel
column chromatography using petroleum ether:chloroform
(2:3) as eluent.
13-(2,4-Dichlorophenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-
12(13H)-one (4f). Yellow solid, mp 252–253ꢀC. IR (KBr) m:
1
3052, 1677, 1232, 1025 cmꢂ1. H NMR (400 MHz, CDCl3) d:
7.89–7.81 (m, 3H), 7.51–7.41 (m, 7H), 7.35–7.31 (m, 1H),
7.02–6.97 (m, 2H), 6.01 (s, 1H) ppm. 13C NMR (100 MHz,
CDCl3) d: 191.6, 167.5, 148.8, 140.1, 136.7, 133.5, 132.9,
132.3, 132.2, 131.9, 131.7, 131.6, 130.4, 130.0,129.4, 128.6,
127.8, 127.5, 125.5, 123.8, 121.7, 118.5, 117.7, 116.5, 110.0,
32.4 ppm. MS (ESI): m/z 429 [M þ H]þ. Anal. calcd for
C26H14Cl2O2: C, 72.74; H, 3.29. found: C, 72.85; H,3.18.
13-(2-Chlorophenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12
(13H)-one (4g). Yellow solid, mp 240–241ꢀC. IR (KBr) m:
13-Phenyl-indeno[1,2-b]naphtho[1,2-e]pyran-12(13H)-one
(4a). Yellow solid, mp 202–203ꢀC. IR (KBr) m: 3080, 1660,
1236, 1006 cmꢂ1 1H NMR (400 MHz, CDCl3) d: 7.89–7.82
.
(m, 3H), 7.51 (d, J ¼ 8.8 Hz, 1H), 7.43–7.29 (m, 8H), 7.23 (t,
J ¼ 8.0 Hz, 2H), 7.12 (t, J ¼ 7.6 Hz, 1H), 5.64 (s, 1H) ppm.
13C NMR (100 MHz, CDCl3) d: 192.3, 167.3, 149.0, 143.7,
136.9, 132.4, 132.2, 131.9, 131.8, 130.1, 129.6, 128.5, 128.4,
128.1, 127.1, 126.6, 125.2, 124.4, 121.6, 118.3, 117.1, 116.6,
111.0, 35.7 ppm. MS (ESI): m/z 361 [M þ H]þ. Anal. calcd
for C26H16O2: C, 86.65; H, 4.47. found: C, 86.73; H, 4.38.
13-(4-Chlorophenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12
(13H)-one (4b). Yellow solid, mp 225–226ꢀC. IR (KBr) m:
1
3048, 1671, 1230, 1018 cmꢂ1. H NMR (400 MHz, CDCl3) d:
7.91–7.81 (m, 3H), 7.51–7.30 (m, 8H), 7.06–7.02 (m, 3H), 6.05
(s, 1H) ppm. 13C NMR (100 MHz, CDCl3) d: 191.7, 167.4, 148.8,
136.8, 132.8, 132.3, 132.2, 131.9, 131.8, 130.8, 130.2, 129.8,
129.7, 128.5, 127.9, 127.4, 127.3, 125.3, 124.1, 121.6, 118.3,
117.7, 117.1, 32.7 ppm. MS (ESI): m/z 395 [M þ H]þ. Anal. calcd
for C26H15ClO2: C, 79.09; H, 3.83. found: C, 79.25; H, 3.92.
13-(4-Methoxylphenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12
(13H)-one (4h). Yellow solid, mp 225–226ꢀC. IR (KBr) m:
1
3042, 1667, 1235, 1015 cmꢂ1. H NMR (400 MHz, CDCl3) d:
1
2945, 1676, 1232, 1004 cmꢂ1. H NMR (400 MHz, CDCl3) d:
7.88–7.84 (m, 2H), 7.75 (t, J ¼ 9.2 Hz, 1H), 7.51 (d, J ¼ 8.8
Hz, 1H), 7.45–7.25 (m, 8H), 7.18 (d, J ¼ 8.4 Hz, 2H), 5.63 (s,
1H) ppm. 13C NMR (100 MHz, CDCl3) d: 192.3, 167.3, 149.0,
142.1, 136.7, 132.3, 132.2, 131.9, 131.6, 130.2, 129.9, 129.5,
128.7, 128.6, 127.3, 125.4, 124.2, 121.7, 118.4, 117.7, 116.0,
110.4, 35.1 ppm. MS (ESI): m/z 395 [M þ H]þ. Anal. calcd for
C26H15ClO2: C, 79.09; H, 3.83. found: C, 79.29; H, 3.75.
7.87–7.82 (m, 3H), 7.49 (d, J ¼ 9.2 Hz, 1H), 7.43–7.27 (m,
6H), 7.23 (d, J ¼ 8.8 Hz, 2H), 6.75 (d, J ¼ 8.8 Hz, 2H), 5.58
(s, 1H), 3.71(s, 3H) ppm. 13C NMR (100 MHz, CDCl3) d:
192.5, 167.0, 158.1, 148.9, 136.9, 136.1, 132.4, 132.2, 131.9,
131.8, 130.0, 129.5, 129.1, 128.4, 127.1, 125.2, 124.4, 121.6,
118.2, 117.7, 116.8, 113.9, 111.2, 55.1, 34.8 ppm. MS (ESI):
m/z 391 [M þ H]þ. Anal. calcd for C27H18O3: C, 83.06; H,
4.65. found: C, 82.96; H, 4.75.
13-(3-Nitrophenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12
(13H)-one (4c). Yellow solid, mp 240–241ꢀC. IR (KBr) m:
1
13-(4-Fluorophenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12
(13H)-one (4i). Yellow solid, mp 208–209ꢀC. IR (KBr) m:
3075, 1665, 1232, 1005 cmꢂ1. H NMR (400 MHz, CDCl3) d:
8.07 (s, 1H), 7.99 (d, J ¼ 8.4 Hz, 1H), 7.93 (d, J ¼ 8.8 Hz, 1H),
7.89–7.87 (m, 1H), 7.79 (d, J ¼ 7.6 Hz, 1H), 7.68 (d, J ¼ 8.8
Hz, 1H), 7.55 (d, J ¼ 9.2 Hz, 1H), 7.47–7.41 (m, 6H), 7.35–7.31
(m, 1H), 5.77 (s, 1H) ppm. 13C NMR (100 MHz, CDCl3) d:
192.1, 167.7, 149.2, 148.5, 145.7, 136.5, 134.4, 132.5, 132.1,
132.0, 131.3, 130.5, 130.4, 129.4, 128.8, 127.5, 125.5, 125.5,
123.9, 123.0, 121.9, 118.7, 117.9, 115.0, 109.5, 35.6 ppm. MS
(ESI): m/z 406 [M þ H]þ. Anal. calcd for C26H15NO4: C, 77.03;
H, 3.73; N, 3.46. found: C, 76.85; H, 3.70; N, 3.58.
1
3052, 1668, 1230, 1016 cmꢂ1. H NMR (400 MHz, CDCl3) d:
7.90–7.76 (m, 3H), 7.50 (d, J ¼ 8.8 Hz, 1H), 7.43–7.28 (m,
8H), 6.91 (t, J ¼ 8.4 Hz, 2H), 5.63 (s, 1H) ppm. 13C NMR
(100 MHz, CDCl3) d: 192.3, 167.2, 149.0, 139.4, 136.8, 132.3,
131.9, 131.7, 130.2, 129.8, 129.7, 129.6, 128.5, 127.2, 125.3,
124.3, 121.7, 118.3, 117.7, 116.3, 115.5, 115.3, 35.0 ppm. MS
(ESI): m/z 379 [M þ H]þ. Anal. calcd for C26H15FO2: C,
82.53; H, 4.00. found: C, 82.44; H, 4.17.
13-(3,4-Dichlorophenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-
12(13H)-ones (4j). Yellow solid, mp 245–246ꢀC. IR (KBr) m:
13-(2-Fluoro-5-(trifluoromethyl)phenyl)-indeno[1,2-b]naph-
tho[1,2-e]pyran-12(13H)-one (4d). Yellow solid, mp 216–
3050, 16728, 1238, 1023 cmꢂ1 1H NMR (400 MHz, CDCl3)
.
217ꢀC. IR (KBr) m: 3042, 1659, 1230, 1007 cmꢂ1 1H NMR
.
d: 7.93–7.86 (m, 2H), 7.73–7.71 (m, 1H), 7.52 (d, J ¼ 9.2 Hz,
1H), 7.48–7.22 (m, 9H), 5.61 (s, 1H) ppm. 13C NMR (100
MHz, CDCl3) d: 192.1, 167.5, 149.1, 143.8, 136.6, 132.6,
132.4, 132.2, 131.9, 131.5, 130.7, 130.4, 130.2, 130.0, 128.7,
127.6, 127.5, 125.5, 124.0, 121.8, 118.5, 117.8, 115.3, 35.0
ppm. MS (ESI): m/z 429 [M þ H]þ. Anal. calcd for
C26H14Cl2O2: C, 72.74; H, 3.29. found: C, 72.60; H,3.40.
(400 MHz, CDCl3) d: 7.91–7.81 (m, 3H), 7.54–7.32 (m, 9H),
7.17 (t, J ¼ 8.8 Hz, 1H), 5.92 (s, 1H) ppm. 13C NMR (100 MHz,
CDCl3) d: 191.7, 168.1, 149.0, 136.6, 132.4, 132.1, 131.9,
131.8, 131.4, 130.5, 130.2, 128.7, 127.6, 127.3, 126.1, 125.5,
124.8, 123.1, 122.1, 121.8, 118.7, 117.8, 116.5, 116.2, 115.2,
109.1, 28.8 ppm. MS (ESI): m/z 447 [M þ H]þ. Anal. calcd for
C27H14F4O2: C, 72.65; H, 3.16. found: C, 72.48; H, 3.12.
13-(4-Methylphenyl)-indeno[1,2-b]naphtho[1,2-e]pyran-12
(13H)-one (4e). Yellow solid, mp 192–193ꢀC. IR (KBr) m:
Acknowledgments. The authors are pleased to acknowledge the
financial support from Xinxiang Medical University.
1
2980, 1675, 1237, 1010 cmꢂ1. H NMR (400 MHz, CDCl3) d:
7.88–7.82 (m, 3H), 7.50 (d, J ¼ 9.2 Hz, 1H), 7.43–7.28 (m,
6H), 7.21 (d, J ¼ 8.0 Hz, 2H), 7.02 (d, J ¼ 8.0 Hz, 2H), 5.61
(s, 1H), 2.24 (s, 3H) ppm. 13C NMR (100 MHz, CDCl3) d:
192.4, 167.2, 149.0, 140.8, 136.9, 136.1, 132.4, 132.2, 131.9,
130.0, 129.5, 129.2, 128.4, 128.0, 127.1, 125.2, 124.4, 121.6,
118.2, 117.7, 116.8, 111.2, 35.3, 21.0 ppm. MS (ESI): m/z 375
REFERENCES AND NOTES
[1] Devi, I.; Bhuyan, P. Tetrahedron Lett 2004, 45, 8625.
[2] Baker, R. A.; Tatum, J. H.; Nemec, S. Mycopathologia
1990, 111, 9.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet