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L. ZARE FEKRI ET AL.
pyranochromenes are known and were compared with authentic samples, matching
melting points (Table 2) and spectra. For the sake of completeness, some representative
data are provided below.
4-(3-Nitrophenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one (4a)
White solid, mp 123-125 ꢀC, FT-IR: (cmꢁ1) 3077, 2938, 1707 (C ¼ O), 1613, 1510, 1495,
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1388 (NO2), 1237 (C-O). H NMR (DMSO-d6): d 5.41 (s, 1H), 7.05-7.92 (m, 14H) ppm.
13C NMR (DMSO-d6): d 162.09, 154.75, 151.54, 147.87, 145.83, 142.49, 139.72, 137.63,
135.87, 130.29, 127.72, 121.92, 119.38, 119.03, 115.82, 114.72, 111.74, 111.62, 109.28,
105.65, 103.34, 34.34 ppm.
Anal. Calc for C24H15NO5: C, 72.54; H, 3.80; N, 3.52. Found: C, 72.51; H, 3.83;
N, 3.55.
4-(4-Nitrophenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one (4b)
White solid, mp 228-230 ꢀC, FT-IR (cmꢁ1) 2918, 1663 (C ¼ O), 1600, 1523, 1356 (NO2),
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1400, 1233 (C-O). H NMR (DMSO-d6): d 5.42 (s, 1H), 7.23-7.97 (m, 14H) ppm. 13C
NMR (DMSO-d6) d 162.24, 154.73, 151.38, 147.48, 145.27, 142.80, 139.48, 137.82,
133.72, 130.59, 121.62, 119.82, 116.04, 115.04, 111.19, 111.98, 109.54, 105.92,
103.60, 37.82 ppm.
Anal. Calc for C24H15NO5: C, 72.54; H, 3.80; N, 3.52. Found: C, 72.53; H, 3.81;
N, 3.54.
4-(4-Hydroxyphenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one (4c)
White solid, mp 167-169 ꢀC, FT-IR (cmꢁ1) 3239, 3069, 2930, 1707 (C ¼ O), 1572, 1486,
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1237 (C-O). H NMR (DMSO-d6) d 5.4 (s, 1H), 6.88-7.92 (m, 14H), 9.8 (s, 1H, phenolic
O-H) ppm. 13C NMR (DMSO-d6) d 160.48, 154.48, 151.58, 149.62, 143.64, 142.756,
139.05, 137.72, 133.83, 130.21, 121.97, 119.24, 116.50, 115.84, 111.37, 111.04, 109.72,
105.78, 103.56, 37.63 ppm.
Anal. Calc for C24H16O4: C, 78.25; H, 4.38. Found: C, 78.21; H, 4.40.
2,4-Diphenylpyrano[3,2-c]chromen-5(4H)-one (4d)
White solid, mp 166-168 ꢀC, FT-IR (cmꢁ1) 3099, 2987, 1665 (C ¼ O), 1609, 1487, 1234
(C-O). 1H NMR (DMSO-d6) d 5.41 (s, 1H), 6.78-7.64 (m, 15H) ppm. 13C NMR
(DMSO-d6) d 165.41, 153.98, 151.09, 147.16, 145.67, 145.12, 143.91, 142.09, 135.87,
128.14, 126.76, 121.45, 115.03, 114.78, 111.38, 111.13, 109.11, 105.21, 36.71ppm.
Anal. Calc for C24H16O3: C, 81.80; H, 4.58. Found: C, 81.81; H, 4.56.
4-(4-Methoxyphenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one (4e)
White solid, mp 143-144 ꢀC, FT-IR (cmꢁ1) 2938, 1666 (C ¼ O), 1495, 1388, 1261 (C-O),
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1102. H NMR (DMSO-d6) d 3.50 (s, 3H), 5.59 (s, 1H), 7.19-8.17 (m, 14H) ppm. 13C