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2-Benzo[1,3]dioxol-5-ylchromen-4-one (4f).24 Yield ¼ 73%
5-Hydroxy-7-methoxy-2-phenylchromen-4-one (4l).27 Yield ¼
(194 mg); white solid; mp ¼ 200–202 ꢀC (recrystallized from 68% (182 mg); white solid; mp ¼ 167–169 ꢀC (recrystallized
hexanes and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for from hexanes and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd
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16H11O4 267.0657, found 267.0650; 1H NMR (400 MHz, CDCl3): for C16H13O4 269.0814, found 269.0821; 1H NMR (400 MHz,
d 8.22 (dd, J ¼ 1.6, 8.0 Hz, 1H), 7.70 (dt, J ¼ 1.6, 8.4 Hz, 1H), 7.55 CDCl3): d 10.81 (br s, 1H), 7.87–7.85 (m, 2H), 7.54–7.48 (m, 3H),
(d, J ¼ 8.0 Hz, 1H), 7.51 (dd, J ¼ 1.6, 8.0 Hz, 1H), 7.42 (dt, J ¼ 0.8, 6.63 (s, 1H), 6.47 (d, J ¼ 2.4 Hz, 1H), 6.35 (d, J ¼ 2.4 Hz, 1H), 3.86
8.0 Hz, 1H), 7.38 (d, J ¼ 1.6 Hz, 1H), 6.94 (d, J ¼ 8.4 Hz, 1H), 6.81 (s, 3H); 13C{1H} NMR (100 MHz, CDCl3): d 182.4, 165.5, 163.9,
(s, 1H), 6.08 (s, 2H); 13C{1H} NMR (100 MHz, CDCl3): d 178.3, 162.1, 157.7, 131.8, 131.2, 129.0 (2ꢁ), 126.2 (2ꢁ), 105.8, 105.6,
163.5, 156.1, 150.8, 148.5, 133.9, 125.7, 125.6, 125.3, 123.6, 98.1, 92.6, 55.7.
121.7, 118.0, 108.8, 106.4, 106.3, 102.0.
5,7-Dimethoxy-2-phenylchromen-4-one (4m).22 Yield ¼ 64%
2-Biphenyl-4-ylchromen-4-one (4g).25 Yield ¼ 80% (238 mg); (181 mg); white solid; mp ¼ 145–147 ꢀC (recrystallized from
white solid; mp ¼ 141–143 ꢀC (recrystallized from hexanes and hexanes and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for
EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for C21H15O2
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17H15O4 283.0970, found 283.0973; 1H NMR (400 MHz, CDCl3):
299.1072, found 299.1077; 1H NMR (400 MHz, CDCl3): d 8.26 d 7.88–7.83 (m, 2H), 7.54–7.45 (m, 3H), 6.67 (s, 1H), 6.56 (d, J ¼
(dd, J ¼ 1.6, 8.0 Hz, 1H), 8.03 (d, J ¼ 8.4 Hz, 2H), 7.76 (d, J ¼ 2.4 Hz, 1H), 6.36 (d, J ¼ 2.0 Hz, 1H), 3.95 (s, 3H), 3.90 (s, 3H); 13
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8.4 Hz, 2H), 7.74 (dt, J ¼ 1.6, 8.4 Hz, 1H), 7.67–7.61 (m, 3H), {1H} NMR (100 MHz, CDCl3): d 177.6, 164.0, 160.9, 160.6, 159.9,
7.51–7.40 (m, 4H), 7.00 (s, 1H), 13C{1H} NMR (100 MHz, CDCl3): 131.5, 131.1, 128.9 (2ꢁ), 125.9 (2ꢁ), 109.3, 109.0, 96.2, 92.8,
d 178.4, 163.6, 156.3, 144.6, 139.7, 134.0, 130.3, 129.0 (2ꢁ), 56.4, 55.7.
128.3, 127.7 (2ꢁ), 127.2 (2ꢁ), 126.9 (2ꢁ), 125.7, 125.4, 123.7,
2-(4-Nitrophenyl)chromen-4-one (4n).21 Yield ¼ 76% (203
mg); white solid; mp ¼ 128–130 ꢀC (recrystallized from hexanes
118.1, 107.1.
2-(3,4-Dimethoxyphenyl)chromen-4-one (4h).26 Yield ¼ 72% and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for C15H10NO4
(203 mg); white solid; mp ¼ 118–120 ꢀC (recrystallized from 268.0610, found 268.0618; 1H NMR (400 MHz, CDCl3): d 8.39 (d,
hexanes and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for J ¼ 9.2 Hz, 2H), 8.24 (dd, J ¼ 1.6, 8.0 Hz, 1H), 8.11 (d, J ¼ 9.2 Hz,
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17H15O4 283.0970, found 283.0976; 1H NMR (400 MHz, CDCl3): 2H), 7.76 (dt, J ¼ 1.6, 8.8 Hz, 1H), 7.61 (dd, J ¼ 0.8, 8.4 Hz, 1H),
d 8.23 (dd, J ¼ 1.6, 8.0 Hz, 1H), 7.70 (dt, J ¼ 1.6, 8.4 Hz, 1H), 7.59 7.47 (dt, J ¼ 1.2, 8.0 Hz, 1H), 6.92 (s, 1H); 13C{1H} NMR (100
(d, J ¼ 8.4 Hz, 1H), 7.58 (d, J ¼ 8.4 Hz, 1H), 7.43 (dt, J ¼ 1.2, MHz, CDCl3): d 178.0, 160.6, 156.2, 149.4, 137.6, 134.4, 127.2
8.0 Hz, 1H), 7.42 (d, J ¼ 8.0 Hz, 1H), 7.00 (d, J ¼ 8.4 Hz, 1H), 6.82 (2ꢁ), 125.9, 125.8, 124.2 (2ꢁ), 123.6, 118.1, 109.6.
(s, 1H), 3.99 (s, 3H), 3.97 (s, 3H); 13C{1H} NMR (100 MHz,
2-Naphthalen-2-ylchromen-4-one (4o).28 Yield ¼ 70% (190
CDCl3): d 178.4, 163.6, 156.2, 152.2, 149.3, 133.7, 125.7, 125.2, mg); white solid; mp ¼ 141–143 ꢀC (recrystallized from hexanes
124.2, 123.8, 120.1, 118.0, 111.2, 108.9, 106.4, 56.1 (2ꢁ).
and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for C19H13O2
2-(3,4-Dichlorophenyl)chromen-4-one (4i).26 Yield ¼ 78% 273.0916, found 273.0925; 1H NMR (400 MHz, CDCl3): d 8.52 (s,
(226 mg); white solid; mp ¼ 202–204 ꢀC (recrystallized from 1H), 8.23 (dd, J ¼ 1.6, 8.0 Hz, 1H), 8.02–7.90 (m, 4H), 7.76 (dt, J ¼
hexanes and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for 1.6, 8.4 Hz, 1H), 7.67 (dd, J ¼ 0.8, 8.4 Hz, 1H), 7.64–7.57 (m, 2H),
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15H9Cl2O2 290.9980, found 290.9987; 1H NMR (400 MHz, 7.47 (dt, J ¼ 1.2, 7.6 Hz, 1H), 7.07 (s, 1H); 13C{1H} NMR (100
CDCl3): d 8.23 (dd, J ¼ 1.6, 8.0 Hz, 1H), 8.24 (d, J ¼ 1.6 Hz, 1H), MHz, CDCl3): d 178.5, 163.7, 156.4, 134.8, 134.0, 132.9, 129.1,
7.75–7.71 (m, 2H), 7.60 (dt, J ¼ 0.8, 8.4 Hz, 2H), 7.45 (dt, J ¼ 0.8, 129.0, 128.8, 128.1, 127.9, 127.1 (2ꢁ), 125.8, 125.4, 123.8, 122.6,
8.0 Hz, 1H), 6.80 (s, 1H); 13C{1H} NMR (100 MHz, CDCl3): 118.1, 107.7.
d 178.1, 160.9, 156.1, 136.0, 134.1, 133.7, 131.7, 131.1, 128.1,
125.8, 125.6, 125.3, 123.9, 118.1, 108.2.
2-(2-Fluorophenyl)chromen-4-one (4p).29 Yield ¼ 67% (161
mg); white solid; mp ¼ 100–102 ꢀC (recrystallized from hexanes
6-Methoxy-2-phenylchromen-4-one (4j).22 Yield ¼ 80% (202 and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for C15H10FO2
mg); white solid; mp ¼ 165–167 ꢀC (recrystallized from hexanes 241.0665, found 241.0669; 1H NMR (400 MHz, CDCl3): d 8.25
and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for C16H13O3 (dd, J ¼ 1.6, 8.0 Hz, 1H), 7.94 (dt, J ¼ 1.6, 8.0 Hz, 1H), 7.72 (dt, J
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253.0865, found 253.0873; H NMR (400 MHz, CDCl3): d 7.94– ¼ 1.6, 8.0 Hz, 1H), 7.57–7.50 (m, 2H), 7.44 (dt, J ¼ 1.2, 7.6 Hz,
7.90 (m, 2H), 7.59 (d, J ¼ 3.2 Hz, 1H), 7.54–7.49 (m, 4H), 7.29 1H), 7.33 (dt, J ¼ 1.2, 8.0 Hz, 1H), 7.24 (dd, J ¼ 1.2, 8.4 Hz, 1H),
(dd, J ¼ 3.2, 9.2 Hz, 1H), 6.87 (s, 1H), 3.90 (s, 3H); 13C{1H} NMR 6.96 (s, 1H); 13C{1H} NMR (100 MHz, CDCl3): d 178.5, 160.6 (d, J
(100 MHz, CDCl3): d 178.3, 163.3, 157.0, 151.1, 131.8, 131.6, ¼ 254.0 Hz), 158.9, 156.4, 133.9, 132.9 (d, J ¼ 9.1 Hz), 129.1,
129.0 (2ꢁ), 126.3 (2ꢁ), 124.4, 123.9, 119.5, 106.7, 104.8, 55.9.
125.8, 125.3 (2ꢁ), 124.6 (d, J ¼ 3.8 Hz), 123.8, 118.1, 117.0 (d, J ¼
7-Methoxy-2-phenylchromen-4-one (4k).22 Yield ¼ 76% (192 22.7 Hz), 112.4 (d, J ¼ 10.6 Hz).
mg); white solid; mp ¼ 106–108 ꢀC (recrystallized from hexanes
2-Furan-2-ylchromen-4-one (4q).30 Yield ¼ 60% (127 mg);
and EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for C16H13O3 white solid; mp ¼ 122–124 ꢀC (recrystallized from hexanes and
253.0865, found 253.0860; 1H NMR (400 MHz, CDCl3): d 8.12 EtOAc); HRMS (ESI-TOF) m/z: [M + H]+ calcd for C13H9O3
(dd, J ¼ 0.4, 8.4 Hz, 1H), 7.91–7.88 (m, 2H), 7.53–7.48 (m, 3H), 213.0552, found 213.0559; 1H NMR (400 MHz, CDCl3): d 8.22
6.99–6.96 (m, 2H), 6.80 (s, 1H), 3.93 (s, 3H); 13C{1H} NMR (100 (dd, J ¼ 2.0, 8.0 Hz, 1H), 7.68 (dt, J ¼ 2.0, 8.4 Hz, 1H), 7.63 (dd, J
MHz, CDCl3): d 177.8, 164.3, 163.2, 158.0, 131.7, 131.5, 129.0 ¼ 0.8, 2.0 Hz, 1H), 7.50 (dd, J ¼ 0.8, 8.4 Hz, 1H), 7.41 (dt, J ¼ 0.8,
(2ꢁ), 127.0, 126.2 (2ꢁ), 117.6, 114.5, 107.3, 100.4, 55.8.
8.0 Hz, 1H), 7.15 (d, J ¼ 3.2 Hz, 1H), 6.76 (s, 1H), 6.62 (dd, J ¼
2.0, 3.2 Hz, 1H); 13C{1H} NMR (100 MHz, CDCl3): d 177.9, 155.8,
© 2021 The Author(s). Published by the Royal Society of Chemistry
RSC Adv., 2021, 11, 11655–11662 | 11659