Deng et al.
3,5-di(furan-2-yl)-1-phenyl-4,5-dihydro-1H-
pyrazole (28)
J = 3.2 Hz), 6.79–6.83 (m, 1H), 6.98 (d, 2H, J = 17.6 Hz), 7.12–7.22
(m, 4H), 7.25–7.30 (m, 1H) p.p.m.; 13C NMR (600 MHz, CDCl3):
d = 154.16, 146.18, 144.12, 139.66, 137.62, 133.95, 132.47, 129.74,
129.09, 128.50, 127.97, 119.42, 113.22, 111.54, 108.02, 60.30,
41.69, 13.91 p.p.m.; MS (EI): m ⁄ z = 370 (M+).
Light yellow crystals, yield: 74.0%; M.p.: 98–100 ꢀC; 1H NMR
(400 MHz, CDCl3): d = 3.33 (dd, 1H, J1 = 6.8 Hz, J2 = 17.2 Hz), 3.67
(dd, 1H, J1 = 12.0 Hz, J2 = 16.6 Hz), 5.33 (dd, 1H, J1 = 6.4 Hz,
J2 = 11.6 Hz), 5.96–5.97 (m, 1H), 6.22–6.34 (m, 1H), 6.49–6.62 (m,
2H), 6.80–6.91 (m, 1H), 7.05–7.12 (m, 2H), 7.20–7.24 (m, 3H), 7.36–
7.47 (m, 1H) p.p.m.; 13C NMR (600 MHz, CDCl3): d = 153.25,
148.08, 144.70, 143.46, 142.28, 139.67, 128.90, 119.72, 113.88,
111.69, 110.50, 109.67, 107.19, 57.71, 39.97 p.p.m.; MS (EI):
m ⁄ z = 278 (M+).
5-(4-bromophenyl)-3-(5-methylfuran-2-yl)-1-
phenyl-4,5-dihydro-1H-pyrazole (33)
1
Yellow crystals, yield: 68.0%; M.p.: 96–98 ꢀC; H NMR (400 MHz,
CDCl3): d = 2.39 (s, 3H), 3.02 (dd, 1H, J1 = 6.8 Hz, J2 = 16.8 Hz),
3.76 (dd, 1H, J1 = 12.4 Hz, J2 = 16.8 Hz), 5.18 (dd, 1H, J1 = 7.2 Hz,
J2 = 12.4 Hz), 6.06–6.08 (m, 1H), 6.43 (d, 1H, J = 3.6 Hz), 6.70–6.71
(m, 1H), 6.78 (t, 1H, J = 3.6 Hz), 7.00 (d, 1H, J = 8.0 Hz), 7.11–7.18
(m, 3H), 7.34–7.36 (m, 1H), 7.43–7.46 (m, 2H) p.p.m.; 13C NMR
(600 MHz, CDCl3): d = 154.06, 146.28, 144.53, 141.35, 139.30,
132.29, 128.96, 127.73, 121.44, 119.33, 113.50, 111.34, 107.98,
63.28, 43.24, 13.92 p.p.m.; MS (EI): m ⁄ z = 380 (M+).
3-(5-methylfuran-2-yl)-5-(4-nitrophenyl)-1-
phenyl-4,5-dihydro-1H-pyrazole (29)
Red crystals, yield: 67.7%; M.p.: 142–144 ꢀC; 1H NMR (400 MHz,
CDCl3): d = 2.39 (s, 3H), 3.04 (dd, 1H, J1 = 6.8 Hz, J2 = 16.8 Hz),
3.83 (dd, 1H, J1 = 12.4 Hz, J2 = 17.2 Hz), 5.32 (dd, 1H, J1 = 6.8 Hz,
J2 = 12.4 Hz), 6.07–6.09 (m, 1H), 6.47 (d, 1H, J = 3.2 Hz), 6.69–6.84
(m, 1H), 6.97–6.99 (m, 2H), 7.15–7.20 (m, 2H), 7.32–7.43 (m, 1H),
7.48–7.50 (m, 1H), 8.15–8.21 (m, 2H) p.p.m.; 13C NMR (600 MHz,
CDCl3): d = 154.30, 149.59, 147.45, 145.95, 144.29, 139.36, 129.09,
126.99, 124.53, 119.68, 113.48, 111.69, 108.08, 63.17, 43.07,
13.89 p.p.m.; MS (EI): m ⁄ z = 347 (M+).
5-(3-fluorophenyl)-3-(5-methylfuran-2-yl)-1-
phenyl-4,5-dihydro-1H-pyrazole (34)
Light yellow crystals, yield: 71.2%; M.p.: 140–142 ꢀC; 1H NMR
(400 MHz, CDCl3): d = 2.39 (s, 3H), 3.05 (dd, 1H, J1 = 7.2 Hz,
J2 = 17.2 Hz), 3.76 (dd, 1H, J1 = 12.4 Hz, J2 = 17.2 Hz), 5.20 (dd,
1H, J1 = 7.2 Hz, J2 = 12.4 Hz), 6.06–6.08 (m, 1H), 6.43–6.44 (m,
1H), 6.77–6.81 (m, 1H), 6.93–6.97 (m, 1H), 7.01–7.03 (m, 3H), 7.09–
7.11 (m, 1H), 7.16–7.20(m, 2H), 7.26–7.37 (m, 1H) p.p.m.; 13C NMR
(600 MHz, CDCl3): d = 164.57, 162.11, 154.07, 146.27, 144.60,
139.35, 130.88, 129.14, 121.54, 119.32, 114.75, 113.49, 113.04,
111.36, 107.97, 63.39, 43.26, 13.89 p.p.m.; MS (EI): m ⁄ z = 320
(M+).
5-(2-chlorophenyl)-3-(5-methylfuran-2-yl)-1-
phenyl-4,5-dihydro-1H-pyrazole (30)
Light yellow crystals, yield: 93.3%; M.p.: 136–138 ꢀC; 1H NMR
(400 MHz, CDCl3): d = 2.39 (s, 3H), 2.96 (dd, 1H, J1 = 6.4 Hz,
J2 = 17.2 Hz), 3.89 (dd, 1H, J1 = 12.4 Hz, J2 = 17.2 Hz), 5.59 (dd,
1H, J1 = 6.4 Hz, J2 = 12.4 Hz), 6.05–6.06 (m, 1H), 6.44 (d, 1H,
J = 1.6 Hz), 6.77–6.81 (m, 1H), 6.97 (d, 2H, J = 8.0 Hz), 7.13–7.23
(m, 5H), 7.43–7.45 (m, 1H) p.p.m.; 13C NMR (600 MHz, CDCl3):
d = 154.04, 146.38, 144.33, 139.64, 138.97, 131.80, 129.92, 129.04,
128.87, 127.66, 127.45, 119.20, 113.24, 111.39, 107.98, 60.69,
41.80, 13.93 p.p.m.; MS (EI): m ⁄ z = 336 (M+).
5-(4-fluorophenyl)-3-(5-methylfuran-2-yl)-1-
phenyl-4,5-dihydro-1H-pyrazole (35)
Orange crystals, yield: 72.1%; M.p.: 100–102 ꢀC; 1H NMR
(400 MHz, CDCl3): d = 2.39 (s, 3H), 3.02 (dd, 1H, J1 = 7.8 Hz,
J2 = 16.8 Hz), 3.76 (dd, 1H, J1 = 12.4 Hz, J2 = 16.8 Hz), 5.21 (dd,
1H, J1 = 6.8 Hz, J2 = 12.0 Hz), 6.05–6.07 (m, 1H), 6.42–6.43 (m,
1H), 6.76–6.80 (m, 1H), 6.99–7.03 (m, 3H), 7.15–7.23 (m, 2H), 7.26–
7.29 (m, 2H), 7.33–7.34 (m, 1H) p.p.m.; 13C NMR (600 MHz, CDCl3):
d = 163.37, 160.92, 154.02, 146.36, 144.60, 139.26, 128.90, 127.61,
119.22, 116.15, 113.50, 111.23, 107.92, 63.20, 43.40, 13.89 p.p.m.;
MS (EI): m ⁄ z = 320 (M+).
5-(4-chlorophenyl)-3-(5-methylfuran-2-yl)-1-
phenyl-4,5-dihydro-1H-pyrazole (31)
Light yellow crystals, yield: 71.6%; M.p.: 98–100 ꢀC; 1H NMR
(400 MHz, CDCl3): d = 2.40 (s, 3H), 3.03 (dd, 1H, J1 = 6.8 Hz,
J2 = 16.8 Hz), 3.78 (dd, 1H, J1 = 12.0 Hz, J2 = 16.8 Hz), 5.21 (dd,
1H, J1 = 6.8 Hz, J2 = 12.4 Hz), 6.08–6.10 (m, 1H), 6.45 (d, 1H,
J = 2.8 Hz), 6.71–6.73 (m, 1H), 6.78–6.82 (m, 1H), 7.02 (d, 1H,
J = 7.6 Hz), 7.17–7.21 (m, 2H), 7.27–7.38 (m, 4H) p.p.m.; 13C NMR
(600 MHz, CDCl3): d = 154.06, 146.28, 144.53, 140.81, 139.31,
133.34, 129.34, 128.90, 128.01, 125.65, 113.50, 111.32, 108.18,
63.24, 43.29, 13.90 p.p.m.; MS (EI): m ⁄ z = 336 (M+).
5-(4-methoxyphenyl)-3-(5-methylfuran-2-yl)-1-
phenyl-4,5-dihydro-1H-pyrazole (36)
Yellow crystals, yield: 70.5%; M.p.: 100–102 ꢀC; 1H NMR
(400 MHz, CDCl3): d = 2.39 (s, 3H), 3.02 (dd, 1H, J1 = 7.2 Hz,
J2 = 16.8 Hz), 3.69–3.81 (m, 4H), 5.17 (dd, 1H, J1 = 6.8 Hz,
J2 = 12.0 Hz), 6.06–6.08 (m, 1H), 6.40–6.41 (m, 1H), 6.74–6.78 (m,
1H), 6.83–6.90 (m, 2H), 7.03–7.05 (m, 1H), 7.14–7.18 (m, 2H), 7.21–
7.26 (m, 2H), 7.31–7.35 (m, 1H) p.p.m.; 13C NMR (600 MHz, CDCl3):
d = 159.00, 153.89, 146.57, 144.78, 139.32, 134.37, 128.98, 127.09,
119.00, 114.49, 113.53, 111.12, 107.91, 63.39, 55.28, 43.46,
13.92 p.p.m.; MS (EI): m ⁄ z = 332 (M+).
5-(2,4-dichlorophenyl)-3-(5-methylfuran-2-yl)-1-
phenyl-4,5-dihydro-1H-pyrazole (32)
Light yellow crystals, yield: 76.7%; M.p.: 160–162 ꢀC; 1H NMR
(400 MHz, CDCl3): d = 2.41 (s, 3H), 2.94 (dd, 1H, J1 = 6.4 Hz,
J2 = 17.2 Hz), 3.88 (dd, 1H, J1 = 12.4 Hz, J2 = 17.2 Hz), 5.54 (dd,
1H, J1 = 6.4 Hz, J2 = 12.0 Hz), 6.06–6.09 (m, 1H), 6.45 (d, 1H,
284
Chem Biol Drug Des 2012; 79: 279–289