The Journal of Organic Chemistry
Page 14 of 20
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8-methoxy-5,6-diphenyl-2H-pyrano[2,3,4-de]chromen-2-one (3m): EtOAc/n-hexane (10:90); green
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crystalline solid (151 mg, 79 %% yield), m. p. 226-227 oC. H NMR (400 MHz, CDCl3) δ 7.45-7.42 (m,
1H), 7.41-7.40 (m, 2H), 7.32-7.30 (m, 1H), 7.30-7.28 (m, 3H), 7.26-7.22 (m, 3H), 7.67 (s, 1H), 7.34 (m,
1H), 5.70 (s, 1H), 3.81 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 164.6, 163.5, 163.4, 155.7, 15.3, 133.6,
132.7, 132.5, 130.7, 129.3, 129.2, 129.1, 128.3, 128.0, 117.1, 105.8, 103.8, 99.7, 86.8, 55.8. HRMS (ESI-
TOF+) m/z calcd. for C24H17O4 [M+H]+ : 369.1121, found: 369.1128.
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8-methoxy-5,6-di-p-tolyl-2H-pyrano[2,3,4-de]chromen-2-one (3n): EtOAc/n-hexane (10:90); pale
yellow crystalline solid (117 mg, 57% yield), m. p. 231-232 oC. 1H NMR (400 MHz, CDCl3) δ 7.19 (d, J =
8 Hz, 2H), 7.17-7.14 (m, 2H), 7.08 (d, J = 8 Hz, 2H), 7.01(d, J = 8 Hz, 2H), 6.07 (s, 1H), 6.29 (s, 1H), 5.64
(s, 1H), 3.77 (s, 3H), 2.38 (s, 3H), 2.29 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 164.6, 163.5, 155.7,
150.33, 139.5, 138.00, 133.15, 130.65, 130.51, 129.9, 129.7, 129.0, 128.7, 116.5, 105.6, 103.8, 99.6,
86.5, 55.8, 21.4. HRMS (ESI-TOF+) m/z calcd. for C26H21O4 [M+H]+ : 397.1434, found: 397.1441
3,3'-(2-oxo-2H-pyrano[2,3,4-de]chromene-5,6-diyl)dibenzonitrile (3o): EtOAc/n-hexane (40:60);
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pale yellow crystalline solid (160 mg, 67 % yield), m. p. 235-236 oC. H NMR (400 MHz, CDCl3) δ 7.75
(d, J = 8 Hz, 1H), 7.63-7.59 (m, 2H), 7.58-7.54 (m, 2H), 7.52-7.49 (m, 2H), 7.42-7.36 (m, 2H), 7.28 (d, J
= 8 Hz. 1H), 7.64 (d, J = 8 Hz, 1H), 5.86 (s,1H). 13C{1H} NMR (100 MHz, CDCl3) δ 162.2, 162.1, 153.7,
148.2, 134.0, 133.1, 132.6, 132.5, 130.5, 129.8, 129.4, 118.1, 117.8, 117.7, 116.8, 116.5, 114.0,
113.1,109.8, 90.8. HRMS (ESI-TOF+) m/z calcd. for C25H14N2O3 [M+H]+ : 389.0921, found: 389.0935.
3,3'-(8-methyl-2-oxo-2H-pyrano[2,3,4-de]chromene-5,6-diyl)dibenzonitrile (3p): EtOAc/n-hexane
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(30:70); brown crystalline solid (141 mg, 62 % yield), m. p. 227-229 oC. H NMR (400 MHz, CDCl3) δ
7.75 (d, J = 8 Hz, 1H), 7.62-7.58 (m, 2H), 7.53 (s, 1H), 7.51-7.48 (m, 2H), 7.41-7.35 (m, 2H), 7.09 (s, 1H),
6.41 (s, 1H), 5.79 (s, 1H), 2.38 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 162.5, 148.3, 146.0, 135.3,
134.6, 134.1, 133.3, 133.1, 132.6, 130.5, 129.3, 118.9, 117.9, 117.7, 116.9, 114.0, 113.0, 107.6, 89.7,
22.4. HRMS (ESI-TOF+) m/z calcd. for C26H16N2O3 [M+H]+ : 403.1077, found: 403.1093.
6-methyl-5-phenylbenzo[de]chromen-2(4H)-one (3q): EtOAc/n-hexane (10:90); off white crystalline
solid (95 mg, 56 % yield), m. p. 142-144 oC. 1H NMR (400 MHz, CDCl3) δ 7.66-7.62 (m, 1H), 7.54 (brs,
1H), 7.53 (brs, 1H), 7.50-7.48 (m, 2H), 7.26 (s, 1H), 7.25-7.22 (m, 1H), 7.17 (d, J = 8 Hz, 1H), 5.71 (s, 1H),
2.19 (s, 3H). 13C{1H} NMR (100 MHz, CDCl3) δ 153.7, 134.0, 132.8, 131.6, 129.8, 129.3, 128.5, 116.2,
150.1, 109.8, 89.2, 13.6. HRMS (ESI-TOF+) m/z calcd. for C18H14O3 [M+H]+ : 277.0859, found: 277.0865.
6,8-dimethyl-5-phenyl-2H-pyrano[2,3,4-de]chromen-2-one (3r): EtOAc/n-hexane (10:90); white
crystalline solid (85 mg, 52 % yield), m. p. 138-139 oC. 1H NMR (400 MHz, CDCl3) δ 7.54-7.53 (m, 1H),
7.52-7.50 (m, 2H), 7.49-7.48 (m, 1H), 7.47 (m, 1H), 7.30 (s, 1H), 6.97 (s, 1H), 5.63 (s, 1H), 2.50 (s, 3H),
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