1114
C.-F. LIU ET AL.
135.50, 144.34, 149.00, 155.37, 155.50, 160.01, and 160þ.62. IR (KBr) 131.35, 132.10, 135.02, 135.11, 144.76, 149.55, 155.36, 155.43,
cmꢂ1: 1720. ESI-HRMS (m/z): calcd for C24H17ClN3O3 [M þ H]þ: 160.24, andþ160.64. IR (KBr) cmꢂ1: 1720. ESI-HRMS (m/z): calcd for
430.0953; found: 430.0946.
C25H20N3O3 [M þ H]þ: 410.1499; found: 410.1489.
7-((4-(4-Chlorophenyl)-4H-1,2,4-triazol-3-yl)methoxy)-4-phenyl-2H-
4-Phenyl-7-((4-(m-tolyl)-4H-1,2,4-triazol-3-yl)methoxy)-2H-chromen-
chromen-2-one (4d)
2-one (4i)
mp 161–163 ꢁC; yield 59%. 1H-NMR (CD-Cl3, 300 MHz): d 5.26 (s, mp 150–152 ꢁC; yield 66%. 1H-NMR (CD-Cl3, 300 MHz): d 2.41 (s,
2H, –OCH2–), 6.24 (s, 1H, C¼CH), 6.87 (d, 1H, J ¼ 8.7 Hz, C¼CH), 3H, –CH3), 5.24 (s, 2H, –OCH2–), 6.24 (s, 1H, C¼CH), 6.88 (d, 1H,
6.95 (s, 1H, C¼CH), 7.38 (s, 1H, C¼CH), 7.41–7.54 (m, 9H, Ar-H), J ¼ 2.4 Hz, C¼CH), 6.95 (s, 1H, C¼CH), 7.21 (d, 1H, J ¼ 5.1 Hz,
8.36 (S, 1H, Triazole-H). 13C-NMR (CD-Cl3, 75 MHz): d 59.76, 102.61, C¼CH), 7.32–7.53 (m, 9H, Ar-H), 8.33 (s, 1H, Triazole-H). 13C-NMR
112.14, 112.38, 113.45, 126.81, 128.32, 128.86, 129.72, 129.71, (CD-Cl3, 75 MHz): d 21.17, 59.66, 102.63, 111.95, 112.35, 113.34,
130.22, 131.85, 135.17, 135.98, 144.70, 149.30, 155.59, 160.24, and 122.18, 125.80, 128.18, 128.73, 129.56, 129.66, 130.57, 133.09,
160.75. IR (KBr) cmꢂ1
:
1714. ESI-HRMS (m/z): calcd for 135.14, 140.23, 144.51, 149.10, 155.41, 155.51, 160.24, and 160.68.
þ
þ
C24H17ClN3O3 [M þ H]þ: 430.0953; found: 430.0946.
IR (KBr) cmꢂ1: 1720. ESI-HRMS (m/z): calcd for C25H20N3O3
[M þ H]þ: 410.1499; found: 410.1489.
7-((4-(4-Fluorophenyl)-4H-1,2,4-triazol-3-yl)methoxy)-4-phenyl-2H-
4-Phenyl-7-((4-(p-tolyl)-4H-1,2,4-triazol-3-yl)methoxy)-2H-chromen-
2-one (4j)
chromen-2-one (4e)
1
mp 190–192 ꢁC; yield 61%. H-NMR (DMSO-d6, 300 MHz): d 5.32 (s,
2H, –OCH2–), 6.17 (s, 1H, C¼CH), 6.85 (dd, 1H, J ¼ 8.7, 2.1 Hz, mp 84–86 ꢁC; yield 68%. 1H-NMR (DMSO-d6, 300 MHz): d 2.34 (s,
C¼CH), 7.08 (s, 1H, C¼CH), 7.24 (s, 1H, C¼CH), 7.29–7.53 (m, 9H, 3H, –CH3), 5.36 (s, 2H, –OCH2–6.27 (s, 1H, C¼CH), 6.92 (dd, 1H,
Ar-H), 8.60 (s, 1H, Triazole-H). 13C-NMR (CD-Cl3-DMSO-d6, 75 MHz): J ¼ 8.7, 2.4 Hz, C¼CH), 7.19 (d, 1H, J ¼ 2.4 Hz, C¼CH), 7.31 (d, 1H,
d 64.88, 107.35, 116.97, 117.49, 117.88, 121.49, 121.80, 132.58, J ¼ 6.9 Hz, C¼CH), 7.33–7.58 (m, 9H, Ar-H), 8.87 (s, 1H, Triazole-H).
132.70, 132.99, 133.25, 133.79, 134.60, 140.04, 150.14, 154.08, 13C-NMR (DMSO-d6, 75 MHz): d 21.03, 49.06, 60.37, 102.81, 112.31,
160.22, 160.42, 165.00, 165.37 (d, Jc–f ¼ 33.75 Hz). IR (KBr) cmꢂ1
:
112.96, 113.32, 125.52, 128.89, 129.33, 130.16, 130.61, 131.47,
þ
1741. ESI-HRMS (m/z): calcd for C24H17FN3O3 [M þ H]þ: 414.1248; 135.31, 139.54, 145.85, 149.29, 155.43, 155.62, 160.31, and 160.83.
þ
found: 414.1235.
IR (KBr) cmꢂ1: 1705. ESI-HRMS (m/z): calcd for C25H20N3O3
[M þ H]þ: 410.1499; found: 410.1489.
7-((4-(3-Bromophenyl)-4H-1,2,4-triazol-3-yl)methoxy)-4-phenyl-2H-
chromen-2-one (4f)
7-((4-(2,4-Dimethylphenyl)-4H-1,2,4-triazol-3-yl)methoxy)-4-phenyl-
2H-chromen-2-one (4k)
1
mp 168–170 ꢁC; yield 58%. H-NMR (DMSO-d6, 300 MHz): d 5.25 (s,
2H, –OCH2–), 6.21 (s, 1H, C¼CH), 6.85 (dd, 1H, J ¼ 9.0, 2.4 Hz, mp 152–154 ꢁC; yield 62%. 1H-NMR (CD-Cl3, 300 MHz): d 2.03 (s,
C¼CH), 6.93 (d, 1H, J ¼ 2.4 Hz, C¼CH), 7.38 (s, 1H, C¼CH), 3H, –CH3), 2.38 (s, 3H, –CH3), 5.15 (s, 2H, –OCH2–), 6.20 (s, 1H,
7.41–7.66 (m, 9H, Ar-H), 8.35 (s, 1H, Triazole-H). 13C-NMR (CD-Cl3- C¼CH), 6.79 (d, 1H, J ¼ 2.1 Hz, C¼CH), 6.82 (s, 1H, C¼CH), 7.11 (s,
DMSO-d6, 75 MHz): d 64.76, 107.35, 117.02, 117.18, 118.12, 127.79, 1H, C¼CH), 7.17–7.51 (m, 8H, Ar-H), 8.21 (s, 1H, Triazole-H). 13C-
128.99, 133.09, 133.36, 133.67, 134.51, 136.12, 137.64, 139.35, NMR (CD-Cl3, 75 MHz): d 17.10, 21.06, 59.80, 102.69, 111.79, 112.44,
139.94, 160.38, 165.09, and 165.30. IR (KBr) cmꢂ1: 1729. ESI-HRMS 113.40, 126.94, 127.80, 128.14, 128.23, 128.77, 129.58, 132.03,
þ
(m/z): calcd for C24H17BrN3O3
474.0437.
[M þ H]þ: 474.0448; found: 134.71, 135.30, 140.78, 144.96, 149.76, 155.42, 155.59, 160.43, anþd
160.66. IR (KBr) cmꢂ1: 1723. ESI-HRMS (m/z): calcd for C26H22N3O3
[M þ H]þ: 424.1656; found: 424.1645.
7-((4-(4-Bromophenyl)-4H-1,2,4-triazol-3-yl)methoxy)-4-phenyl-2H-
chromen-2-on (4g)
7-((4-(2,6-Dimethylphenyl)-4H-1,2,4-triazol-3-yl)methoxy)-4-phenyl-
2H-chromen-2-one (4l)
mp 96–98 ꢁC; yield 64%. 1H-NMR (CD-Cl3, 300 MHz): d 5.25 (s, 2H,
–OCH2–), 6.26 (s, 1H, C¼CH), 6.88 (dd, 1H, J ¼9.0, 2.4 Hz, C¼CH), mp 160–162 ꢁC; yield 58%. 1H-NMR (CD-Cl3, 300 MHz): d 2.01 (s,
6.95 (d, 1H, J ¼ 2.4 Hz, C¼CH), 7.30 (s, 1H, C¼CH), 7.33–7.70 (m, 6H, –CH3), 5.10 (s, 2H, –OCH2–), 6.22 (s, 1H, C¼CH), 6.77 (d, 1H,
9H, Ar-H), 8.34 (s, 1H, Triazole-H). 13C-NMR (CD-Cl3, 75 MHz): d J ¼2.7 Hz, C¼CH), 6.81 (d, 1H, J ¼ 1.8 Hz, C¼CH), 7.19 (s, 1H,
59.56, 102.54, 111.89, 112.43, 113.46, 124.03, 126.84, 128.20, C¼CH), 7.30–7.54 (m, 8H, Ar-H), 8.18 (s, 1H, Triazole-H). 13C-NMR
128.26, 128.75, 129.59, 132.18, 133.15, 135.09, 144.37, 149.04, (CD-Cl3, 75 MHz): d 17.52, 60.10, 102.68, 111.62, 112.69, 113.55,
155.40, 155.51, 160.03, and 160.65. IR (KBr) cmꢂ1: 1718. ESI-HRMS 128.26, 128.31, 128.84, 128.88, 129.65, 130.32, 135.70, 144.44,
þ
(m/z): calcd for C24H17BrN3O3
474.0437.
[M þ H]þ: 474.0448; found: 155.46, 155.66, 160.52, and 160.72. IR (KBr) cmꢂ1: 1723. ESI-HRMS
þ
(m/z): calcd for C26H22N3O3 [M þ H]þ: 424.1656; found: 424.1645.
4-Phenyl-7-((4-(o-tolyl)-4H-1,2,4-triazol-3-yl)methoxy)-2H-chromen-
2-on (4h)
7-((4-(4-Methoxyphenyl)-4H-1,2,4-triazol-3-yl)methoxy)-4-phenyl-
2H-chromen-2-one (4m)
mp 112–114 ꢁC; yield 63%. 1H-NMR (CD-Cl3, 300 MHz): d 2.22 (s, mp 158–160 ꢁC; yield 67%. 1H-NMR (CD-Cl3, 300 MHz): d 3.87 (s,
3H, –CH3), 5.31 (s, 2H, –OCH2–), 6.35 (s, 1H, C¼CH), 6.91 (d, 1H, 3H, –OCH3), 5.23 (s, 2H, –OCH2–), 6.25 (s, 1H, C¼CH), 6.90 (d, 1H,
J ¼ 2.7 Hz, C¼CH), 6.95 (d, 1H, J ¼ 1.8 Hz, C¼CH), 7.36 (d, 1H, J ¼ 2.4 Hz, C¼CH), 6.93 (s, 1H, C¼CH), 7.00 (s, 1H, C¼CH), 7.03–7.54
J ¼ 7.8 Hz, C¼CH), 7.41–7.66 (m, 9H, Ar-H), 8.38 (s, 1H, Triazole-H). (m, 9H, Ar-H), 8.31 (s, 1H, Triazole-H). 13C-NMR (CD-Cl3, 75 MHz): d
13C-NMR (CD-Cl3, 75 MHz): d 17.17, 59.74, 102.48, 111.68, 112.29, 55.69, 59.70, 102.76, 112.09, 112.46, 113.47, 115.06, 125.83, 126.81,
113.25, 127.10, 127.12, 128.10, 128.16, 128.71, 129.55, 130.46, 128.33, 128.87, 129.71, 135.29, 144.97, 149.57, 155.59, 155.65,