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Huijun Xie et al.: Synthesis and Activity of New Schiff Bases of Furocoumarin
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heated to 140 °C and stirred for 24 h. The Se was filtered (s, 1H). C NMR(151 MHz, CDCl ): δ 161.12, 157.54, 156.42,
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and the resulting filtrate was evaporated. Compound 5 152.59, 150.82, 147.06, 146.10, 129.63,127.94, 125.18,124.55,
was acquired via column chromatography purification. 121.12, 119.56, 118.72, 113.31, 107.13, 100.21. IR (KBr) v:
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Yield 63%, yellow solid, m.p. 176–177°C; H NMR (400 1705,1633, 1449, 1154, 1132, 761 cm ; HRMS (ESI) calcd for
+
MHz, CDCl ) δ 10.14 (s, 1H), 8.90 (s, 1H), 7.72 (d, J = 2.1 Hz, C H NO [M+H] 290.0812, found 290.0798.
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18 12
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1H), 7.54 (s, 1H), 6.89 (d, J = 2.0 Hz, 1H), 6.86 (s, 1H).
(Z)-5-((4-Methoxyphenyl)imino)methyl-
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H-furo[3,2-g]chromen-7-one (6e). Yield 34%, light
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yellow solid, m.p. 188–190°C; H NMR (400 MHz, CDCl ):
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General synthesis method of Schiff bases 6a–6k
δ 9.18 (s,1H), 8.69 (s, 1H), 7.70 (d, J= 2.2 Hz, 1H), 7.53 (s, 1H),
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.39 (d, J= 8.9 Hz, 2H), 7.01(d, J= 8.9 Hz, 2H), 6.89 (d, J= 2.0
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A mixture of Compound 5 (1.0 mmol) and corresponding Hz, 1H), 6.76 (s, 1H), 3.88 (s, 3H). C NMR(151 MHz, CDCl ):
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aniline (3.0 mmol) in ethanol (20 ml) was refluxed. After δ 161.26, 160.05, 156.35, 154.52, 152.58, 146.98, 146.37,
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4 h, the reaction was evaporated and purified by silica 143.46, 125.08,122.99, 119.55, 117.85, 116.80, 114.84, 113.50,
gel chromatography to furnish 6a–6k.
107.12, 100.14, 55.74. IR (KBr) v:2924, 2843, 1706, 1631, 1560,
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+
(
Z)-5-((2-methylphenyl)imino)methyl-7H-furo[3,2- 1446, 1153, 759 cm ; HRMS (ESI) calcd for C H NO [M+H]
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14
4
g]chromen-7-one (6a). Yield 40%, light yellow solid, m.p. 320.0917, found 320.0940.
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1
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81–183°C; H NMR (400 MHz, CDCl ): δ 9.23 (s,1H), 8.59 (s,
(Z)-5-((3,4-Dimethylphenyl)imino)methyl-
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H), 7.71 (d, J= 2.1 Hz, 1H), 7.55 (s, 1H), 7.34–7.26 (m, 3H), 7.03 7H-furo[3,2-g]chromen-7-one (6f). Yield 33%, light
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(
(
d, J= 7.2 Hz, 1H), 6.87 (d, J= 1.9 Hz, 1H), 6.79 (s, 1H), 2.46 yellow solid, m.p. 165–167°C; H NMR (400 MHz, CDCl ):
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s, 3H). C NMR (101MHz, CDCl ): δ 161.19, 156.77, 156.38, δ 9.17 (s,1H), 8.66 (s, 1H), 7.70 (d, J= 2.2 Hz, 1H), 7.52 (s,
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52.62, 149.92, 147.06, 146.14, 133.02,130.91, 127.79, 127.19, 1H), 7.23 (d, J= 7.9 Hz, 1H), 7.16(s, 1H), 7.11 (dd, J= 7.9, 2.0
25.17, 119.59, 118.71, 117.10, 113.41, 107.12, 100.20, 18.35. Hz, 1H), 6.89 (d, J= 2.1Hz, 1H), 6.74 (s, 1H), 2.34 (s,3H),
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IR (KBr) v: 2924, 2853, 1709, 1634, 1448, 1156, 1134, 1012, 2.32 (s, 3H). C NMR (101 MHz, CDCl ): δ 161.19, 156.33,
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60 cm ; HRMS (ESI) calcd for C H NO [M+H] 304.0968, 156.08,152.56,148.46, 146.97, 146.29, 137.97, 136.96,
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found 304.0990.
130.70, 125.09, 122.64, 119.61, 118.45,118.20, 113.41,
(
Z ) - 5 - ( ( 4 - M e t h y l p h e n y l ) i m i n o ) m e t h y l - 107.13, 100.10, 20.02, 19.65. IR (KBr) v: 2923, 2855, 1704,
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H-furo[3,2-g]chromen-7-one (6b). Yield 38%, light 1637,1568, 1447, 1157, 1130, 762 cm ; HRMS (ESI) calcd for
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+
yellow solid, m.p. 193–194°C; H NMR (400 MHz, CDCl ): C H NO [M+H] 318.1125, found 318.1145.
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20 16
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δ 9.18 (s,1H), 8.67 (s, 1H), 7.70 (d, J= 2.2 Hz, 1H), 7.54 (s,
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(Z)-5-((4-Fluorophenyl)imino)methyl-7H-furo[3,2-
H), 7.05 (d, J= 8.1 Hz, 2H), 6.90–6.85 (m, 3H), 6.77 (s, 1H), g]chromen-7-one (6g). Yield 30%, light yellow solid,
.42 (s, 3H). 13C NMR (151 MHz, CDCl ): δ 161.19,156.35, m.p. 179–181°C; H NMR (400 MHz, CDCl ): δ 9.13 (s,1H),
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52.60, 148.19, 147.01, 146.27, 138.29, 130.24, 125.14, 121.21, 8.65 (s, 1H), 7.71 (d, J= 2.2 Hz, 1H), 7.54 (s, 1H), 7.39–7.31 (m,
19.60,118.35, 116.04, 113.42, 107.14, 100.17, 21.31; IR (KBr) v: 2H), 7.22–7.12(m, 2H), 6.89 (d, J= 1.9 Hz, 1H), 6.77 (s, 1H).
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926, 2851, 1707, 1630,1445, 1150, 1135, 1011, 944, 759 cm ;
C NMR (101 MHz, CDCl ): δ 161.23,157.07, 152.77, 151.77,
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HRMS (ESI) calcd for C H NO [M+H] 304.0968, found 147.39, 146.97, 145.95, 125.17, 122.97, 119.44, 118.71,116.69,
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04.0948.
116.40, 113.64, 107.10, 106.68, 100.03. IR (KBr) v: 1720,
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(
Z)-5-((4-Chlorophenyl)imino)methyl-7H-furo[3,2- 1625, 1569, 1450,1228, 1082, 755 cm ; HRMS (ESI) calcd for
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g]chromen-7-one (6c). Yield 31%, yellow solid, m.p. C H FNO [M+H] 308.0717, found 308.0693.
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00–202°C; H NMR (600 MHz, CDCl ): δ 9.13 (s,1H),8.64 (s,
H), 7.71 (d, J= 2.0 Hz, 1H), 7.55 (s, 1H), 7.45 (d, J= 7.4 Hz, 2H), 7H-furo[3,2-g]chromen-7-one (6h). Yield 28%, light
(Z)-5-((3,4-Difluorophenyl)imino)methyl-
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.28 (d, J= 8.2 Hz, 2H), 6.89 (d, J= 1.9 Hz, 1H), 6.78 (s, 1H). C yellow solid, m.p. 163–164°C; H NMR (400 MHz, CDCl ): δ
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NMR (151 MHz, CDCl ): δ 160.84, 157.72, 147.23, 146.99, 9.09 (s, 1H), 8.62 (s, 1H), 7.69 (d, J= 2.2 Hz, 1H), 7.49 (s, 1H),
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145.68, 138.10, 133.61, 129.65, 125.06, 124.42,122.36, 113.02, 6.91–6.89 (m, 2H),6.87–6.84 (m, 2H), 6.79 (s, 1H). C NMR (101
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19.28, 118.88, 106.96, 100.14. IR (KBr) v: 1717, 1623, 1576, MHz, CDCl ): δ 161.26, 156.47,154.30, 152.79, 147.39, 146.98,
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234,1076 cm ; HRMS (ESI) calcd for C H ClNO [M+H]
145.23, 132.69, 127.82, 124.57, 119.15, 116.70,113.66, 110.18,
108.74, 106.68, 100.32. IR (KBr) v: 1722, 1630, 1569, 1457, 1334,
Z)-5-(Phenylimino)methyl-7H-furo[3,2-g]chro- 1231,1100, 763 cm ; HRMS (ESI) calcd for C H F NO [M+H]
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24.0422, found 324.0440.
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(
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men-7-one (6d). Yield 36%, yellow solid, m.p. 210–211°C; 326.0623, found326.0651.
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H NMR (600 MHz, CDCl ): δ 9.16 (s, 1H), 8.66 (s,1H), 7.71
( Z ) - 5 - ( ( 3 - C h l o r o p h e n y l ) i m i n o ) m e t h y l -
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(
d, J= 2.1 Hz, 1H), 7.55 (s, 1H), 7.51–7.46 (m, 2H), 7.36 (t, J=7.4 7H-furo[3,2-g]chromen-7-one (6i). Yield 31%, yellow
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Hz,1H), 7.33 (d, J= 7.4 Hz, 2H), 6.89 (d, J = 2.1 Hz, 1H), 6.78 solid, m.p. 192–193°C; H NMR (600 MHz, CDCl ): δ 9.12 (s,
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