Molecules 2016, 21, 1198
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1-(4-Fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3-(3-ethoxy-2-hydroxyphenyl)-3a,6a-dihydro-1H-pyrrolo[3,4-
c]pyrazole-4,6-dione (10c): Pale yellow solid; 1H-NMR (CDCl3)
7.46–7.39 (m, 3H), 7.08–6.93 (m, 6H),
δ
6.83 (t, J = 8.4 Hz, 2H), 4.98–4.91 (m, 2H), 4.16 (q, 2H), 3.82–3.77 (m, 2H), 2.93–2.83 (m, 2H), 1.51
(t, J = 6.9 Hz, 3H) ppm; MS (EI, m/z) 491 [M]+; HRMS (EI) m/z calcd C27H23F2N3O4 [M]+ 491.1657,
found 491.1654.
1-(4-Fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3-(2-hydroxy-3-methoxy-5-nitrophenyl)-3a,6a-dihydro-1H-
pyrrolo[3,4-c]pyrazole-4,6-dione (11): Pale yellow solid; 1H-NMR (CDCl3)
δ 8.52 (d, J = 2.7 Hz, 1H), 7.84
(d, J = 2.7 Hz, 1H), 7.45–7.40 (m, 2H), 7.11 (t, J = 8.1 Hz, 2H), 7.03–6.98 (m, 2H), 6.81 (t, J = 8.4 Hz, 2H),
5.08 (d, J = 10.8 Hz, 1H), 4.98 (d, J = 11.1 Hz, 1H), 4.05 (s, 3H), 3.85 (t, J = 7.8 Hz, 2H), 2.90 (t, J = 6.9 Hz,
2H) ppm; MS (ESI, m/z) 521 [M
found 521.1281.
−
H]+; HRMS (ESI) m/z calcd C26H19F2N4O6 [M
−
H]+; 521.1273,
3-(2,3-Dimethoxyphenyl)-1-(4-fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3a,6a-dihydro-1H-pyrrolo[3,4-
c]pyrazole-4,6-dione (12a): Pale yellow solid; 1H-NMR (CDCl3)
7.52–7.47 (m, 2H), 7.26–7.23 (m, 1H),
7.12–6.98 (m, 6H), 6.90 (t, J = 8.7 Hz, 2H), 5.23 (d, J = 10.8 Hz, 1H), 4.97 (d, J = 10.8 Hz, 1H), 3.99 (s, 3H),
δ
3.91 (s, 3H), 3.77–3.71 (m, 2H), 2.85 (t, J = 7.2 Hz, 2H) ppm; MS (ESI, m/z) 490 [M
−
H]+; HRMS (ESI)
m/z calcd C27H22F2N3O4 [M − H]+ 490.1578, found 490.1586.
3-Benzo[1,3]dioxol-4-yl-1-(4-fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3a,6a-dihydro-1H-pyrrolo[3,4-
c]pyrazole-4,6-dione (12b): Pale yellow solid; 1H-NMR (CDCl3)
7.53–7.49 (m, 2H), 7.36–7.34 (m, 1H),
7.08–7.01 (m, 4H), 6.92–6.85 (m, 4H), 6.09 (s, 2H), 5.02–4.94 (m, 2H), 3.75 (t, J = 6.9 Hz, 2H), 2.85
δ
(t, J = 7.5 Hz, 2H) ppm; MS (ESI, m/z) 474 [M
474.1265, found 474.1259.
−
H]+; HRMS (ESI) m/z calcd C26H18F2N3O4 [M
−
H]+
1-(4-Fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3-(2-hydroxynaphthalen-1-yl)-3a,6a-dihydro-1H-pyrrolo[3,4-
c]pyrazole-4,6-dione (13): Pale yellow solid; 1H-NMR (CDCl3)
7.97 (d, J = 2.1 Hz, 1H), 7.83–7.75 (m,
δ
2H), 7.517.39 (m, 4H), 7.176.99 (m, 5H), 6.87 (t, J = 8.7 Hz, 2H), 5.55 (d, J = 10.8 Hz, 1H), 5.00 (d,
J = 10.5 Hz, 1H), 3.69 (t, J = 7.2 Hz, 2H), 2.80 (t, J = 7.5 Hz, 2H) ppm; MS (EI, m/z) 497 [M]+; HRMS (EI)
m/z calcd C29H21F2N3O3 [M]+ 497.1551, found 497.1553.
1-(4-Fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3-thiazol-2-yl-3a,6a-dihydro-1H-pyrrolo[3,4-c]pyrazole-4,6-dione
(
14a): Yellow solid; 1H-NMR (CDCl3)
δ
7.97 (d, J = 3.0 Hz, 1H), 7.54–7.50 (m, 2H), 7.40 (d, J = 3.0 Hz,
1H), 7.18–7.14 (m, 1H), 7.04–6.97 (m, 3H), 6.85 (t, J = 8.4 Hz, 2H), 5.14–5.03 (m, 2H), 3.81 (t, J = 6.9 Hz,
2H), 2.88 (t, J = 6.9 Hz, 2H) ppm; MS (ESI, m/z) 437 [M
[M − H]+ 437.0884, found 437.0880.
−
H]+; HRMS (ESI) m/z calcd C22H15F2N4O2S
1-(4-Fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3-pyridin-2-yl-3a,6a-dihydro-1H-pyrrolo[3,4-c]pyrazole-4,6-dione
1
(
14b): Pale yellow solid; H-NMR (CDCl3)
δ
8.75 (m, 1H), 7.98–7.96 (m, 1H), 7.81–7.78 (m, 1H),
7.34–7.32 (m, 1H), 7.21–7.15 (m, 3H), 7.08–6.96 (m, 5H), 5.53 (d, J = 10.8 Hz, 1H), 5.14 (d, J = 10.8 Hz,
1H), 3.75–3.70 (m, 2H), 2.89-2.84 (m, 2H) ppm; MS (ESI, m/z) 431 [M
−
H]+; HRMS (ESI) m/z calcd
C24H17F2N4O2 [M − H]+ 431.1320, found 431.1318.
1-(3-Fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3-(2-hydroxy-3-methoxyphenyl)-3a,6a-dihydro-1H-pyrrolo[3,4-
c]pyrazole-4,6-dione (15a): Pale yellow solid; 1H-NMR (CDCl3)
7.48–7.45 (m, 1H), 7.34–7.13 (m, 3H),
δ
7.04–6.94 (m, 4H), 6.87–6.81 (m, 2H), 6.78–6.72 (m, 1H), 5.03 (d, J = 10.8 Hz, 1H), 4.94 (d, J = 10.5 Hz,
1H), 3.96 (s, 3H), 3.81 (t, J = 7.5 Hz, 2H), 2.87 (t, J = 7.2 Hz, 2H) ppm; MS (ESI, m/z) 477 [M]+; HRMS
(ESI) m/z calcd C26H21F2N3O4 [M]+ 477.1500, found 477.1489.
1-(2-Fluorophenyl)-5-[2-(4-fluorophenyl)ethyl]-3-(2-hydroxy-3-methoxyphenyl)-3a,6a-dihydro-1H-pyrrolo[3,4-
c]pyrazole-4,6-dione (15b): Pale yellow solid; 1H-NMR (CDCl3)
δ
7.52–7.49 (m, 1H), 7.28–7.26 (m, 1H),
7.19–7.12 (m, 3H), 6.98–6.90 (m, 4H), 6.81 (t, J = 8.4 Hz, 2H), 5.41–5.37 (m, 1H), 4.83 (d, J = 10.5 Hz, 1H),
3.96 (s, 3H), 3.75 (t, J = 6.9 Hz, 2H), 2.81 (t, J = 7.2 Hz, 2H) ppm; MS (ESI, m/z) 476 [M
(ESI) m/z calcd C26H20F2N3O4 [M − H]+ 476.1422, found 476.1419.
−
H]+; HRMS