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The Journal of Organic Chemistry
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Hz, 1H), 7.48 – 7.43 (m, 1H), 7.36 – 7.33 (m, 6H), 7.29 – 7.23 (m, 7H), 7.16 (t, J = 8.2 Hz, 3H),
5.95 (s, 1H), 5.51 (d, J = 1.9 Hz, 1H), 2.64 (q, J = 7.6 Hz, 2H), 1.23 (t, J = 7.6 Hz, 3H). 13C{1H}
NMR (101 MHz, CDCl3) δ 171.1, 160.1, 152.7, 145.7, 142.8, 137.2, 134.5, 131.7, 128.8, 128.7,
128.6, 127.6, 127.6, 127.0, 126.9, 124.7, 121.8, 116.0, 94.7, 65.7, 28.6, 15.3. HRMS (ESI): calcd
for C32H26NO2 (M+H)+ 456.1958, found 456.1971.
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4-(4-Methoxyphenyl)-2,2-diphenyl-1,2-dihydro-5H-chromeno[2,3-b]pyridin-5-one
(3e).
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Yellow solid, mp 222 – 223 °C , 44.5 mg, 97% yield. H NMR (400 MHz, CDCl3) δ 8.03 (dd, J =
7.9, 1.4 Hz, 1H), 7.45 (dd, J = 11.2, 4.2 Hz, 1H), 7.37 – 7.31 (m, 8H), 7.30 – 7.25 (m, 4H), 7.24 –
7.20 (m, 1H), 7.16 (d, J = 8.2 Hz, 1H), 6.85 (d, J = 8.7 Hz, 2H), 6.03 (s, 1H), 5.49 (d, J = 1.9 Hz,
1H), 3.77 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) δ 171.1, 160.1, 158.6, 152.7, 145.6, 134.1,
132.3, 131.7, 128.8, 128.6, 127.6, 127.0, 126.4, 124.7, 124.3, 121.4, 116.0, 112.8, 94.6, 65.6, 55.1.
HRMS (ESI): calcd for C31H24NO3 (M+H)+ 458.1751, found 458.1762.
4-([1,1'-Biphenyl]-4-yl)-2,2-diphenyl-1,2-dihydro-5H-chromeno[2,3-b]pyridin-5-one
(3f).
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White solid, mp 246 – 247 °C , 48.4 mg, 96% yield. H NMR (400 MHz, CDCl3) δ 8.09 (dd, J =
7.9, 1.6 Hz, 1H), 7.63 – 7.58 (m, 2H), 7.57 – 7.53 (m, 2H), 7.51 – 7.46 (m, 1H), 7.44 – 7.40 (m,
3H), 7.39 – 7.34 (m, 8H), 7.33 – 7.24 (m, 5H), 7.21 (d, J = 7.8 Hz, 1H), 5.78 (s, 1H), 5.59 (d, J =
2.0 Hz, 1H). 13C{1H} NMR (101 MHz, CDCl3) δ 171.2, 160.1, 152.8, 145.6, 141.2, 139.8, 139.0,
134.3, 131.9, 128.7, 128.6, 128.2, 127.7, 127.1, 127.0, 127.0, 126.5, 126.2, 124.8, 124.3, 122.2,
116.1, 94.6, 65.7. HRMS (ESI): calcd for C36H26NO2 (M+H)+ 504.1958, found 504.1973.
4-(4-Fluorophenyl)-2,2-diphenyl-1,2-dihydro-5H-chromeno[2,3-b]pyridin-5-one (3g). Yellow
solid, mp 237 – 239 °C , 41.2 mg, 92% yield. 1H NMR (400 MHz, CDCl3) δ 8.03 (d, J = 7.9, 1H),
7.48 – 7.43 (m, 1H), 7.39 – 7.32 (m, 8H), 7.32 – 7.22 (m, 5H), 7.17 (d, J = 8.3 Hz, 1H), 6.98 (t, J
= 8.7 Hz, 2H), 6.02 (s, 1H), 5.49 (d, J = 1.9 Hz, 1H). 13C{1H} NMR (101 MHz, CDCl3) δ 171.1,
162.0 (d, J(C, F) = 245.4 Hz), 160.1, 152.7, 145.5, 135.8 (d, J(C, F) = 3.0 Hz), 133.7, 131.9, 129.3
(d, J(C, F) = 8.1 Hz), 128.6, 127.7, 127.0, 126.3, 124.8, 124.2, 122.0, 116.0, 114.2 (d, J(C, F) =
21.2 Hz), 94.4, 65.7. 19F{1H} NMR (376 MHz, CDCl3) δ -115.7. HRMS (ESI): calcd for
C30H21FNO2 (M+H)+ 446.1551, found 446.1560.
4-(4-Chlorophenyl)-2,2-diphenyl-1,2-dihydro-5H-chromeno[2,3-b]pyridin-5-one (3h). Pale
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yellow solid, mp 223 – 224 °C , 43.8 mg, 95% yield. H NMR (400 MHz, CDCl3) δ 8.05 (dd, J =
7.9, 1.5 Hz, 1H), 7.50 – 7.45 (m, 1H), 7.39 – 7.33 (m, 8H), 7.32 – 7.24 (m, 7H), 7.20 (d, J = 8.3
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