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H, 4.29; Br, 16.20; N, 5.68; O, 12.97. Found: C, 60.59; H, 4.27; N,
5.70.
Calcd for C24H18BrFN2O3: C, 59.89; H, 3.77; Br, 16.60; F, 3.95; N,
5.82; O, 9.97. Found: C, 59.52; H, 3.74; N, 5.82.
4.5.6. (3,5-Bis(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-
yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone (C6)
4.5.12. (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(3-
fluorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-
yl)methanone (C12)
White crystal, mp: 144–146 °C. 1H NMR (CDCl3, 300 MHz) d:
3.12–3.18 (d, J = 16.8 Hz, 1H), 3.69–3.76 (m, 1H), 3.82 (s, 6H),
4.31–4.33 (t, J = 2.4 Hz, 4H), 5.72–5.77 (m, 1H), 6.83–6.90 (m,
3H), 7.19–7.23 (m, 2H), 7.43–7.46 (m, 1H), 7.59 (s, 1H), 7.71–
7.74 (d, J = 8.1 Hz, 2H), 7.82–7.84 (d, J = 7.2 Hz, 2H). MS (ESI):
445.17 (C26H25N2O5, [M+H]+). Anal. Calcd for C26H24N2O5: C,
70.26; H, 5.44; N, 6.30; O, 18.00. Found: C, 69.97; H, 5.44; N, 6.32.
White crystal, mp: 162–163 °C. 1H NMR (CDCl3, 300 MHz) d:
3.11–3.17 (m, 1H), 3.70–3.80 (m, 1H), 3.86 (s, 3H), 4.32–4.37 (t,
J = 5.4 Hz, 4H), 5.76–5.82 (m, 1H), 6.91–6.98 (m, 4H), 7.03 (s, 1H),
7.10–7.13 (d, J = 7.8 Hz, 1H), 7.66–7.70 (m, 4H), 7.74 (s, 1H). MS
(ESI): 433.15 (C25H22FN2O4, [M+H]+). Anal. Calcd for C25H21FN2O4:
C, 69.44; H, 4.89; F, 4.39; N, 6.48; O, 14.80. Found: C, 69.16; H, 4.87;
N, 6.49.
4.5.7. (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(4-
fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-
yl)methanone (C7)
4.5.13. (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(2-
fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-
yl)methanone (C13)
White crystal, mp: 137–138 °C. 1H NMR (CDCl3, 300 MHz) d:
3.20–3.26 (d, J = 17.4 Hz, 1H), 3.76–3.81 (m, 1H), 4.33–4.34 (t,
J = 2.1 Hz, 4H), 5.76–5.82 (m, 1H), 7.05–7.12 (m, 3H), 7.25–7.28
(m, 2H), 7.45–7.51 (m, 4H), 7.59 (s, 1H), 7.65–7.68 (d, J = 8.1 Hz,
2H). MS (ESI): 403.14 (C24H20FN2O3, [M+H]+). Anal. Calcd for
White crystal, mp: 176–177 °C. 1H NMR (CDCl3, 300 MHz) d:
3.20–3.27 (m, 1H), 3.81–3.86 (m, 1H), 4.39–4.41 (t, J = 4.2 Hz,
4H), 5.62–5.69 (m, 1H), 6.91–6.99 (m, 2H), 7.21–7.24 (d,
J = 9.0 Hz, 1H), 7.43–7.46 (m, 3H), 7.50–7.54 (m, 3H), 7.60 (s, 1H),
7.71–7.74 (d, J = 7.8 Hz, 2H). MS (ESI): 403.14 (C24H20FN2O3,
[M+H]+). Anal. Calcd for C24H19FN2O3: C, 71.63; H, 4.76; F, 4.72;
N, 6.96; O, 11.93. Found: C, 71.35; H, 4.75; N, 7.00.
C24H19FN2O3: C, 71.63; H, 4.76; F, 4.72; N, 6.96; O, 11.93. Found:
C, 71.31; H, 4.75; N, 6.97.
4.5.8. (3-(4-Bromophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-
pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone
(C8)
4.5.14. (3-(4-Bromophenyl)-5-(2-fluorophenyl)-4,5-dihydro-1H-
pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone
(C14)
Yellow crystal, mp: 226–229 °C. 1H NMR (CDCl3, 300 MHz) d:
3.19–3.24 (d, J = 16.2 Hz, 1H), 3.74–3.79 (m, 1H), 4.32–4.33 (t,
J = 3.0 Hz, 4H), 5.69–5.75 (m, 1H), 7.02–7.10 (m, 3H), 7.23–7.25
(m, 2H), 7.47–7.54 (m, 3H), 7.60 (s, 1H), 7.68–7.71 (d, J = 7.8 Hz,
2H). MS (ESI): 481.05 (C24H19BrFN2O3, [M+H]+). Anal. Calcd for
White crystal, mp: 140–141 °C. 1H NMR (CDCl3, 300 MHz) d:
3.23–3.29 (d, J = 17.1 Hz, 1H), 3.80–3.87 (m, 1H), 4.35–4.37 (t,
J = 3.9 Hz, 4H), 5.63–5.69 (m, 1H), 6.90–6.96 (m, 2H), 7.11 (m,
1H), 7.33–7.35 (d, J = 6.6 Hz, 1H), 7.47–7.50 (m, 4H), 7.59 (s, 1H),
7.66–7.69 (d, J = 8.4 Hz, 2H). MS (ESI): 481.05 (C24H19BrFN2O3,
[M+H]+). Anal. Calcd for C24H18BrFN2O3: C, 59.89; H, 3.77; Br,
16.60; F, 3.95; N, 5.82; O, 9.97. Found: C, 59.72; H, 3.74; N, 5.82.
C24H18BrFN2O3: C, 59.89; H, 3.77; Br, 16.60; F, 3.95; N, 5.82; O,
9.97. Found: C, 59.66; H, 3.75; N, 5.83.
4.5.9. (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(4-
fluorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-
yl)methanone (C9)
4.5.15. (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(2-
fluorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-
yl)methanone (C15)
White crystal, yield mp: 236–237 °C. 1H NMR (CDCl3, 300 MHz)
d: 3.18–3.23(d, J = 16.8 Hz, 1H), 3.72–3.78 (m, 1H), 3.82 (s, 3H),
4.31–4.32 (t, J = 2.7 Hz, 4H), 5.72–5.78 (m, 1H), 7.04–7.11 (m,
5H), 7.22–7.25 (m, 2H), 7.43–7.49 (m, 1H), 7.58 (s, 1H), 7.74–
7.76 (d, J = 7.2 Hz, 2H). MS (ESI): 433.15 (C25H22FN2O4, [M+H]+).
Anal. Calcd for C25H21FN2O4: C, 69.44; H, 4.89; F, 4.39; N, 6.48; O,
14.80. Found: C, 69.08; H, 4.86; N, 6.49.
White crystal, mp: 173–175 °C. 1H NMR (CDCl3, 300 MHz) d:
3.18–3.24 (d, J = 16.8 Hz, 1H), 3.71–3.81 (m, 1H), 3.85 (s, 3H),
4.49–4.51 (t, J = 5.1 Hz, 4H), 5.67–5.69 (m, 1H), 6.91–6.99 (m,
4H), 7.07–7.11 (d, J = 8.7 Hz, 1H), 7.42–7.47 (m, 3H), 7.59 (s, 1H),
7.75–7.78 (d, J = 8.7 Hz, 2H). MS (ESI): 433.15 (C25H22FN2O4,
[M+H]+). Anal. Calcd for C25H21FN2O4: C, 69.44; H, 4.89; F, 4.39;
N, 6.48; O, 14.80. Found: C, 69.01; H, 4.86; N, 6.48.
4.5.10. (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(3-
fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-
yl)methanone (C10)
4.5.16. (2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)(3,5-diphenyl-4,5-
dihydro-1H-pyrazol-1-yl)methanone (D1)
White crystal, mp: 201 °C. 1H NMR (CDCl3, 300 MHz) d: 3.21–
3.27 (m, 1H), 3.79–3.83 (m, 1H), 4.38–4.46 (m, 1H), 4.53–4.63
(m, 1H), 5.59–5.66 (m, 2H), 6.82–6.88 (m, 3H), 6.99–7.00 (d,
J = 4.8 Hz, 1H), 7.21–7.26 (m, 3H), 7.30–7.34 (m, 2H), 7.44–7.48
(m, 3H), 7.75–7.76 (d, J = 3.9 Hz, 2H). MS (ESI): 385.15
(C24H21N2O3, [M+H]+). Anal. Calcd for C24H20N2O3: C, 74.98; H,
5.24; N, 7.29; O, 12.49. Found: C, 74.61; H, 5.23; N, 7.31.
White crystal, mp: 105–107 °C. 1H NMR (CDCl3, 300 MHz) d:
3.19–3.24 (d, J = 16.2 Hz, 1H), 3.65–3.73 (m, 1H), 4.32 (t,
J = 2.1 Hz, 4H), 5.72–5.78 (m, 1H), 6.78 (s, 1H), 6.95–7.09 (m, 3H),
7.23–7.26 (m, 1H), 7.44–7.53 (m, 4H), 7.57 (s, 1H), 7.62–7.65 (d,
J = 8.4 Hz, 2H). MS (ESI): 403.14 (C24H20FN2O3, [M+H]+). Anal. Calcd
for C24H19FN2O3: C, 71.63; H, 4.76; F, 4.72; N, 6.96; O, 11.93. Found:
C, 71.37; H, 4.74; N, 6.98.
4.5.17. (3-(4-Bromophenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-
1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methanone (D2)
Yellow crystal, mp: 233–235 °C. 1H NMR (CDCl3, 300 MHz) d:
3.16–3.23 (d, J = 10.2 Hz, 1H), 3.75–3.82 (m, 1H), 4.35–4.45 (m,
1H), 4.52–4.61 (m, 1H), 5.57–5.63 (m, 2H), 6.92–6.97 (d,
J = 10.8 Hz, 2H), 7.31–7.44 (m, 4H), 7.57–7.62 (m, 4H), 7.69–7.72
(m, 3H). MS (ESI): 463.06 (C24H20BrN2O3, [M+H]+). Anal. Calcd for
4.5.11. (3-(4-Bromophenyl)-5-(3-fluorophenyl)-4,5-dihydro-1H-
pyrazol-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanone
(C11)
Yellow crystal, mp: 135–137 °C. 1H NMR (CDCl3, 300 MHz) d:
3.22–3.27 (d, J = 16.5 Hz, 1H), 3.77–3.82 (m, 1H), 4.34 (t,
J = 2.1 Hz, 4H), 5.70–5.76 (m, 1H), 6.79 (s, 1H), 6.91–7.05 (m, 3H),
7.31–7.33 (m, 1H), 7.49–7.57 (m, 3H), 7.61 (s, 1H), 7.68–7.71 (d,
J = 7.5 Hz, 2H). MS (ESI): 481.05 (C24H19BrFN2O3, [M+H]+). Anal.
C24H19BrN2O3: C, 62.22; H, 4.13; Br, 17.25; N, 6.05; O, 10.36.
Found: C, 61.93; H, 4.11; N, 6.05.