Chem. J. Chinese Universities ›› 2022, Vol. 43 ›› Issue (10): 20220274.doi: 10.7503/cjcu20220274
• Organic Chemistry • Previous Articles Next Articles
Received:
2022-04-24
Online:
2022-10-10
Published:
2022-06-17
Contact:
ZHANG Xiaofei
E-mail:zhangxiaofei@sust.edu.cn
Supported by:
CLC Number:
TrendMD:
ZHANG Xiaofei, LIU Jiaxin. Visible Light Induced Cyclization of O-Alkenylcarboxanilide to 2-Quinolinone[J]. Chem. J. Chinese Universities, 2022, 43(10): 20220274.
Compd. | m. p./℃ | HRMS, m/z[M+Na]+(calcd.) | Compd. | m. p./℃ | HRMS, m/z[M+Na]+(calcd.) |
---|---|---|---|---|---|
1a | 104—106 | 242.0788(242.0781) | 1i | 133—135 | 300.0842(300.0837) |
1b | 132—134 | 310.0661(310.0657) | 1j | 114—116 | 256.0944(256.0937) |
1c | 122—123 | 267.0740(267.0736) | 1k | 137—138 | 319.9893(319.9885) |
1d | 124—126 | 326.0611(326.0605) | 1l | 124—126 | 310.0661(310.0656) |
1e | 122—123 | 260.0693(260.0687) | 1m | 114—116 | 256.0944(256.0937) |
1f | 105—106 | 276.0398(276.0393) | 1n | 130—133 | 272.0893(272.0890) |
1g | 135—136 | 319.9893(319.9887) | 1o | 131—133 | 256.0944(256.0937) |
1h | 126—128 | 298.1414(298.1408) |
Table 1 Melting points(m. p.) and HRMS data of compounds 1a—1o
Compd. | m. p./℃ | HRMS, m/z[M+Na]+(calcd.) | Compd. | m. p./℃ | HRMS, m/z[M+Na]+(calcd.) |
---|---|---|---|---|---|
1a | 104—106 | 242.0788(242.0781) | 1i | 133—135 | 300.0842(300.0837) |
1b | 132—134 | 310.0661(310.0657) | 1j | 114—116 | 256.0944(256.0937) |
1c | 122—123 | 267.0740(267.0736) | 1k | 137—138 | 319.9893(319.9885) |
1d | 124—126 | 326.0611(326.0605) | 1l | 124—126 | 310.0661(310.0656) |
1e | 122—123 | 260.0693(260.0687) | 1m | 114—116 | 256.0944(256.0937) |
1f | 105—106 | 276.0398(276.0393) | 1n | 130—133 | 272.0893(272.0890) |
1g | 135—136 | 319.9893(319.9887) | 1o | 131—133 | 256.0944(256.0937) |
1h | 126—128 | 298.1414(298.1408) |
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS, m/z[M+H]+(calcd.) |
---|---|---|---|---|
2a | White solid | 93 | 198—199[ | 146.0607(146.0606) |
2b | White solid | 88 | 202—203 | 214.0482(214.0480) |
2c | Pale yellow solid | 70 | >320 | 171.0553(170.0545) |
2d | White solid | 93 | 222—224 | 230.0423(230.0418) |
2e | Pale yellow solid | 90 | 270—273[ | 164.5110(164.512) |
2f | Yellow solid | 78 | 265—267[ | 180.0213(180.0216) |
2g | Yellow solid | 77 | 268—269[ | 223.9715(223.9711) |
2h | White solid | 83 | >320 | 202.1240(202.1232) |
2i | White solid | 80 | 251—253[ | 204.0582(204.0582) |
2j | White solid | 86 | 236—237[ | 160.0758(160.0762) |
2k | Yellow solid | 75 | 304—306 | 223.9715(223.9711) |
2l | White solid | 74 | 244—246 | 214.0482(214.0480) |
2m | White solid | 86 | 190—193[ | 160.0760(160.0762) |
2n | Pale yellow solid | 72 | 199—200 | 176.0711(176.0712) |
2o | White solid | 78 | 220—221[ | 160.0760(160.0762) |
Table 2 Appearance, yields, melting points(m. p.) and HRMS data of compounds 2a—2o
Compd. | Appearance | Yield(%) | m. p./℃ | HRMS, m/z[M+H]+(calcd.) |
---|---|---|---|---|
2a | White solid | 93 | 198—199[ | 146.0607(146.0606) |
2b | White solid | 88 | 202—203 | 214.0482(214.0480) |
2c | Pale yellow solid | 70 | >320 | 171.0553(170.0545) |
2d | White solid | 93 | 222—224 | 230.0423(230.0418) |
2e | Pale yellow solid | 90 | 270—273[ | 164.5110(164.512) |
2f | Yellow solid | 78 | 265—267[ | 180.0213(180.0216) |
2g | Yellow solid | 77 | 268—269[ | 223.9715(223.9711) |
2h | White solid | 83 | >320 | 202.1240(202.1232) |
2i | White solid | 80 | 251—253[ | 204.0582(204.0582) |
2j | White solid | 86 | 236—237[ | 160.0758(160.0762) |
2k | Yellow solid | 75 | 304—306 | 223.9715(223.9711) |
2l | White solid | 74 | 244—246 | 214.0482(214.0480) |
2m | White solid | 86 | 190—193[ | 160.0760(160.0762) |
2n | Pale yellow solid | 72 | 199—200 | 176.0711(176.0712) |
2o | White solid | 78 | 220—221[ | 160.0760(160.0762) |
Compd. | 1H NMR(400 MHz, DMSO?d6), δ | 13C NMR(100 MHz, DMSO?d6), δ |
---|---|---|
2a | 11.70(s, 1H), 7.92(d J=9.3 Hz, 1H) , 7.68(d, J=7.8 Hz, 1H), 7.53(t, J=7.3 Hz, 1H) , 7.34(d, J=8.2 Hz, 1H), 7.21(t J=7.4 Hz, 1H) , 6.52(d, J=9.5 Hz, 1H) | 162.39, 140.68, 139.32, 130.79, 128.31, 122.34, 122.20, 119.56, 115.58 |
2b | 12.06(s, 1H), 8.11(s, 1H), 8.04(d, J=9.6 Hz, 1H), 7.80(d, J=8.6 Hz, 1H), 7.48(d, J=8.6 Hz, 1H), 6.64(d, J=9.6 Hz, 1H) | 162.41, 141.77, 140.32, 126.93(q, J=4 Hz), 125.92 (q, J=4 Hz), 123.85, 123.40, 123.09(q, J=32 Hz),119.15, 116.57 |
2c | 12.14(s, 1H), 8.25(s, 1H), 7.95(d, J=9.6 Hz, 1H), 7.87(d, J=8.5 Hz, 1H), 7.41(d, J=9.6 Hz, 1H) | 162.30, 142.19, 139.90, 133.56, 133.35, 124.15, 119.59, 119.29, 116.75, 104.32 |
2d | 11.92(s, 1H), 7.98(d, J=9.6 Hz, 1H), 7.76(d, J=1.6 Hz, 1H), 7.54(dd, J=9.0 Hz, 2.0 Hz, 1H), 7.42(d, J=8.6 Hz, 1H), 6.62(d, J=9.6 HZ, 1H) | 162.18, 142.87, 139.89, 138.26, 124.14, 123.89, 120.66(q, J=254 Hz), 120.25, 120.06, 117.34 |
2e | 11.79(s, 1H), 7.91(d, J=9.6 Hz, 1H), 7.57(dd, J=9.1 Hz, 2.6 Hz, 1H), 7.44(dd, J=8.9 Hz, 2.6 Hz, 1H), 7.36(dd, J=8.9 Hz, 4.9 Hz, 1H) | 162.04, 158.53, 156.16, 139.83(d, J=3 Hz), 123.68, 120.24(d, J=9 Hz), 118.89(d, J=24.3 Hz), 117.38(d, J=8.2 Hz), 113.17(d, J=22.8 Hz) |
2f | 11.84(s, 1H), 7.91(d, J=9.6 Hz, 1H), 7.81(d, J=1.8 Hz, 1H), 7.57(dd, J=8.7 Hz, 1.9 Hz, 1H), 7.35(d, J=8.8 Hz, 1H) | 162.10, 139.60, 138.11, 130.62, 127.32, 126.00, 123.67, 120.73, 117.43 |
2g | 11.85(s, 1H), 7.95(d, J=2.0 Hz, 1H), 7.91(d, J=9.6 Hz, 1H), 7.68(dd, J=8.7 Hz, 2.1 Hz, 1H), 7.30(d, J=8.7 Hz, 1H), 6.59(d, J=9.6 Hz, 1H) | 166.84, 144.30, 143.18, 138.04, 135.08, 128.36, 126.02, 122.47, 118.48 |
2h | 11.60(s, 1H), 7.91(d, J=9.5 Hz, 1H), 7.64(d, J=1.8 Hz, 1H), 7.61(dd, J=8.6 Hz, 2.0 Hz, 1H), 7.29(d, J=8.6 Hz, 1H), 6.49(d, J=9.5 Hz, 1H), 1.34(s, 9H) | 162.37, 144.56, 140.96, 137.26, 128.65, 124.13, 122.13, 119.16, 115.35, 34.57, 31.61 |
2i | 12.05(s, 1H), 8.37(d, J=1.8 Hz, 1H), 8.10—8.06(m, 2H), 7.42(d, J=8.6 Hz, 1H), 6.62(d, J=9.6 Hz, 1H), 3.92(s, 3H) | 166.18, 162.53, 142.57, 140.91, 131.07, 130.38, 123.36, 123.22, 119.15, 115.90 |
2j | 11.62(s, 1H), 7.85(d, J=9.52 Hz, 1H), 7.46(s, 1H), 7.35(dd, J=8.4 Hz, 1.6 Hz, 1H), 7.26(d, J=8.4 Hz, 1H), 6.49(d, J=9.5 Hz, 1H), 2.36(s, 1H) | 162.60, 140.83, 137.01, 132,21, 131.64, 127.86, 121,92, 119.64, 115.62, 20.74 |
2k | 11.77(s, 1H), 7.93(d, J=9.6 Hz, 1H), 7.65(d, J=8.4 Hz, 1H), 7.51(d, J=1.4 Hz, 1H), 7.37(dd, J=8.4 Hz, 1.8 Hz, 1H), 6.56(d, J=9.6 Hz, 1H) | 162.15, 140.45, 140.25, 130.27, 125.12, 123.87,122.88, 118.67, 117.85 |
2l | 11.98(s, 1H), 8.04(d, J=9.6 Hz, 1H), 7.93(d, J=8.2 Hz, 1H), 7.65(s, 1H), 7.51(d, J=8.2 Hz, 1H), 6.70(d, J=9.6 Hz, 1H) | 162.29, 140.06, 139.07, 130.98(q, J=31.6 Hz), 129.78, 125.67, 124.92, 122.19, 118.28(q, J=3.4 Hz), 112.48(q, J=4 Hz) |
2m | 11.70(s, 1H), 7.86(d, J=9.5 Hz, 1H), 7.55(d, J=7.9 Hz, 1H), 7.12(s, 1H), 7.01(d, J=7.9 Hz, 1H), 6.43(d, J=9.4 Hz, 1H), 2.39(s, 3H) | 162.27, 140.37, 137.35, 131.97, 131.10, 127.80, 122.34, 119.52, 115.48, 20.78 |
2n | 12.07(s, 1H), 8.37(d, J=1.6 Hz, 1H), 8.10—8.06(m, 2H), 7.42(d, J=8.6 Hz, 1H), 6.63(d, J=9.6 Hz, 1H), 3.91(s, 1H) | 116.17, 162.51, 142.59, 140.88, 131.06, 130.38, 123.36, 123.23, 119.15, 115.89, 52.52 |
2o | 9.46(s, 1H), 7.81(d, J=9.5 Hz, 1H), 7.47(d, J=7.5 Hz, 1H), 7.40(d, J=7.3 Hz, 1H), 7.18(t, J=7.6 Hz, 1H), 6.71(d, J=9.5 Hz, 1H), 2.53(s, 1H) | 163.04, 141.19, 136.81, 131.76, 126.11, 122.17, 122.22, 121.47, 119.65 |
Table 3 1 H NMR and 13C NMR data of compounds 2a—2o*
Compd. | 1H NMR(400 MHz, DMSO?d6), δ | 13C NMR(100 MHz, DMSO?d6), δ |
---|---|---|
2a | 11.70(s, 1H), 7.92(d J=9.3 Hz, 1H) , 7.68(d, J=7.8 Hz, 1H), 7.53(t, J=7.3 Hz, 1H) , 7.34(d, J=8.2 Hz, 1H), 7.21(t J=7.4 Hz, 1H) , 6.52(d, J=9.5 Hz, 1H) | 162.39, 140.68, 139.32, 130.79, 128.31, 122.34, 122.20, 119.56, 115.58 |
2b | 12.06(s, 1H), 8.11(s, 1H), 8.04(d, J=9.6 Hz, 1H), 7.80(d, J=8.6 Hz, 1H), 7.48(d, J=8.6 Hz, 1H), 6.64(d, J=9.6 Hz, 1H) | 162.41, 141.77, 140.32, 126.93(q, J=4 Hz), 125.92 (q, J=4 Hz), 123.85, 123.40, 123.09(q, J=32 Hz),119.15, 116.57 |
2c | 12.14(s, 1H), 8.25(s, 1H), 7.95(d, J=9.6 Hz, 1H), 7.87(d, J=8.5 Hz, 1H), 7.41(d, J=9.6 Hz, 1H) | 162.30, 142.19, 139.90, 133.56, 133.35, 124.15, 119.59, 119.29, 116.75, 104.32 |
2d | 11.92(s, 1H), 7.98(d, J=9.6 Hz, 1H), 7.76(d, J=1.6 Hz, 1H), 7.54(dd, J=9.0 Hz, 2.0 Hz, 1H), 7.42(d, J=8.6 Hz, 1H), 6.62(d, J=9.6 HZ, 1H) | 162.18, 142.87, 139.89, 138.26, 124.14, 123.89, 120.66(q, J=254 Hz), 120.25, 120.06, 117.34 |
2e | 11.79(s, 1H), 7.91(d, J=9.6 Hz, 1H), 7.57(dd, J=9.1 Hz, 2.6 Hz, 1H), 7.44(dd, J=8.9 Hz, 2.6 Hz, 1H), 7.36(dd, J=8.9 Hz, 4.9 Hz, 1H) | 162.04, 158.53, 156.16, 139.83(d, J=3 Hz), 123.68, 120.24(d, J=9 Hz), 118.89(d, J=24.3 Hz), 117.38(d, J=8.2 Hz), 113.17(d, J=22.8 Hz) |
2f | 11.84(s, 1H), 7.91(d, J=9.6 Hz, 1H), 7.81(d, J=1.8 Hz, 1H), 7.57(dd, J=8.7 Hz, 1.9 Hz, 1H), 7.35(d, J=8.8 Hz, 1H) | 162.10, 139.60, 138.11, 130.62, 127.32, 126.00, 123.67, 120.73, 117.43 |
2g | 11.85(s, 1H), 7.95(d, J=2.0 Hz, 1H), 7.91(d, J=9.6 Hz, 1H), 7.68(dd, J=8.7 Hz, 2.1 Hz, 1H), 7.30(d, J=8.7 Hz, 1H), 6.59(d, J=9.6 Hz, 1H) | 166.84, 144.30, 143.18, 138.04, 135.08, 128.36, 126.02, 122.47, 118.48 |
2h | 11.60(s, 1H), 7.91(d, J=9.5 Hz, 1H), 7.64(d, J=1.8 Hz, 1H), 7.61(dd, J=8.6 Hz, 2.0 Hz, 1H), 7.29(d, J=8.6 Hz, 1H), 6.49(d, J=9.5 Hz, 1H), 1.34(s, 9H) | 162.37, 144.56, 140.96, 137.26, 128.65, 124.13, 122.13, 119.16, 115.35, 34.57, 31.61 |
2i | 12.05(s, 1H), 8.37(d, J=1.8 Hz, 1H), 8.10—8.06(m, 2H), 7.42(d, J=8.6 Hz, 1H), 6.62(d, J=9.6 Hz, 1H), 3.92(s, 3H) | 166.18, 162.53, 142.57, 140.91, 131.07, 130.38, 123.36, 123.22, 119.15, 115.90 |
2j | 11.62(s, 1H), 7.85(d, J=9.52 Hz, 1H), 7.46(s, 1H), 7.35(dd, J=8.4 Hz, 1.6 Hz, 1H), 7.26(d, J=8.4 Hz, 1H), 6.49(d, J=9.5 Hz, 1H), 2.36(s, 1H) | 162.60, 140.83, 137.01, 132,21, 131.64, 127.86, 121,92, 119.64, 115.62, 20.74 |
2k | 11.77(s, 1H), 7.93(d, J=9.6 Hz, 1H), 7.65(d, J=8.4 Hz, 1H), 7.51(d, J=1.4 Hz, 1H), 7.37(dd, J=8.4 Hz, 1.8 Hz, 1H), 6.56(d, J=9.6 Hz, 1H) | 162.15, 140.45, 140.25, 130.27, 125.12, 123.87,122.88, 118.67, 117.85 |
2l | 11.98(s, 1H), 8.04(d, J=9.6 Hz, 1H), 7.93(d, J=8.2 Hz, 1H), 7.65(s, 1H), 7.51(d, J=8.2 Hz, 1H), 6.70(d, J=9.6 Hz, 1H) | 162.29, 140.06, 139.07, 130.98(q, J=31.6 Hz), 129.78, 125.67, 124.92, 122.19, 118.28(q, J=3.4 Hz), 112.48(q, J=4 Hz) |
2m | 11.70(s, 1H), 7.86(d, J=9.5 Hz, 1H), 7.55(d, J=7.9 Hz, 1H), 7.12(s, 1H), 7.01(d, J=7.9 Hz, 1H), 6.43(d, J=9.4 Hz, 1H), 2.39(s, 3H) | 162.27, 140.37, 137.35, 131.97, 131.10, 127.80, 122.34, 119.52, 115.48, 20.78 |
2n | 12.07(s, 1H), 8.37(d, J=1.6 Hz, 1H), 8.10—8.06(m, 2H), 7.42(d, J=8.6 Hz, 1H), 6.63(d, J=9.6 Hz, 1H), 3.91(s, 1H) | 116.17, 162.51, 142.59, 140.88, 131.06, 130.38, 123.36, 123.23, 119.15, 115.89, 52.52 |
2o | 9.46(s, 1H), 7.81(d, J=9.5 Hz, 1H), 7.47(d, J=7.5 Hz, 1H), 7.40(d, J=7.3 Hz, 1H), 7.18(t, J=7.6 Hz, 1H), 6.71(d, J=9.5 Hz, 1H), 2.53(s, 1H) | 163.04, 141.19, 136.81, 131.76, 126.11, 122.17, 122.22, 121.47, 119.65 |
Entry | Catalyst | Solvent b | Base | Yield c (%) | Entry | Catalyst | Solvent b | Base | Yield c (%) |
---|---|---|---|---|---|---|---|---|---|
1 | PC?A | DMSO | NaCO3 | 57 | 13 | PC?B | THF | NaCO3 | 56 |
2 | PC?B | DMSO | NaCO3 | 78 | 14 | PC?B | CH3OH | NaCO3 | 82 |
3 | PC?C | DMSO | NaCO3 | 54 | 15 | PC?B | CH3OH | K2CO3 | 93 |
4 | PC?D | DMSO | NaCO3 | 44 | 16 | PC?B | CH3OH | K3PO4 | 70 |
5 | Ru(bpy)3Cl2 | DMSO | NaCO3 | 56 | 17 | PC?B | CH3OH | KH2PO4 | 67 |
6 | Eosin Y | DMSO | NaCO3 | 33 | 18 | PC?B | CH3OH | Cs2CO3 | 77 |
7 | PC?B | CH3CN | NaCO3 | 50 | 19 | PC?B | CH3OH | CsOAc | 57 |
8 | PC?B | DMF | NaCO3 | 36 | 20 | PC?B | CH3OH | KOAc | 55 |
9 | PC?B | Toluene | NaCO3 | 40 | 21 | PC?B | CH3OH | LiOAc | 45 |
10 | PC?B | Acetone | NaCO3 | 48 | 22 | PC?B | CH3OH | None | 10 |
11 | PC?B | DCE | NaCO3 | 50 | 23 d | PC?B | CH3OH | K2CO3 | NR |
12 | PC?B | 1,4?Dioxane | NaCO3 | 45 |
Table 4 Optimization of reaction conditions a
Entry | Catalyst | Solvent b | Base | Yield c (%) | Entry | Catalyst | Solvent b | Base | Yield c (%) |
---|---|---|---|---|---|---|---|---|---|
1 | PC?A | DMSO | NaCO3 | 57 | 13 | PC?B | THF | NaCO3 | 56 |
2 | PC?B | DMSO | NaCO3 | 78 | 14 | PC?B | CH3OH | NaCO3 | 82 |
3 | PC?C | DMSO | NaCO3 | 54 | 15 | PC?B | CH3OH | K2CO3 | 93 |
4 | PC?D | DMSO | NaCO3 | 44 | 16 | PC?B | CH3OH | K3PO4 | 70 |
5 | Ru(bpy)3Cl2 | DMSO | NaCO3 | 56 | 17 | PC?B | CH3OH | KH2PO4 | 67 |
6 | Eosin Y | DMSO | NaCO3 | 33 | 18 | PC?B | CH3OH | Cs2CO3 | 77 |
7 | PC?B | CH3CN | NaCO3 | 50 | 19 | PC?B | CH3OH | CsOAc | 57 |
8 | PC?B | DMF | NaCO3 | 36 | 20 | PC?B | CH3OH | KOAc | 55 |
9 | PC?B | Toluene | NaCO3 | 40 | 21 | PC?B | CH3OH | LiOAc | 45 |
10 | PC?B | Acetone | NaCO3 | 48 | 22 | PC?B | CH3OH | None | 10 |
11 | PC?B | DCE | NaCO3 | 50 | 23 d | PC?B | CH3OH | K2CO3 | NR |
12 | PC?B | 1,4?Dioxane | NaCO3 | 45 |
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