Med Chem Res
H5,6-phthalimide), 7.99 (dd, 2H, J = 8 Hz, J = 4 Hz, H4,7
-
167.2 (C=O). Elemental anal. for C14H8FNO2, Calculated:
C, 69.71; H, 3.34; N, 5.81; O, 13.27. Found: C, 69.73; H,
3.38; N, 5.84; O, 13.35.
phthalimide). 13CNMR (DMSO-d6, 62.5 MHz) d: 123.8
(C2,6), 127.7 (C4,7), 129.3 (C3,5), 130.2 (C3a,7a), 131.6 (C1),
133.8 (C4), 134.6 (C5,6), 167.0 (C=O). Elemental anal. for
C14H8ClNO2, Calculated: C, 65.26; H, 3.13; N, 5.44; O,
12.42. Found: C, 65.32; H, 3.09; N, 5.49; O, 12.47.
2-(2-Nitrophenyl)isoindoline-1,3-dione (3h)
m.p: 139 °C, Yield: 74 %, MW: 268 g/mol, orange pow-
der, IR (KBr, cm-1) t: 2924 (C–H, stretch, asymmetric,
aliphatic), 1720 (C=O, stretch), 1519 (NO2, stretch,
asymmetric), 1346 (NO2, stretch, asymmetric). 1HNMR
(CDCl3, 400 MHz) d: 7.57 (d, 1H, J = 8 Hz, H6-2-nitro-
phenyl), 7.67 (t, 1H, J = 8 Hz, H4-2-nitrophenyl), 7.85 (t,
1H, J = 8 Hz, H5-2-nitrophenyl), 7.86 (dd, 2H, J = 8 Hz,
J = 4 Hz, H5,6-phthalimide), 8.02 (dd, 2H, J = 8 Hz,
J = 4 Hz, H4,7-phthalimide), 8.23 (d, 1H, J = 8 Hz, H3-2-
nitrophenyl). 13CNMR (DMSO-d6, 62.5 MHz) d: 123.6
(C4,7), 125.5 (C6), 126.2 (C3), 128.7 (C4), 131.3 (C1), 133.6
(C5), 134.1 (C3a,7a), 135.9 (C5,6), 148.3 (C2), 164.1 (C=O).
MS (m/z, %): 268 (M?, 5), 222 (100), 194 (5), 166 (15),
140 (12), 104 (12), 76 (22). Elemental anal. for
C14H8N2O4, Calculated: C, 62.69; H, 3.01; N, 10.44; O,
23.86. Found: C, 62.72; H, 3.11; N, 10.48; O, 23.81.
2-(2-Fluorophenyl)isoindoline-1,3-dione (3e)
m.p: 181 °C, Yield: 59 %, MW: 291 g/mol, white powder,
IR (KBr, cm-1) t: 3074 (C–H, aromatic), 1720 (C=O,
stretch), 1593 (C=C, stretch, aromatic), 1462 (C=C, stretch,
aromatic). 1HNMR (CDCl3, 400 MHz) d: 7.79 (m, 2H,
2-fluorophenyl), 7.84 (m, 2H, 2-fluorophenyl), 7.87 (dd,
2H, J = 8 Hz, J = 4 Hz, H5,6-phthalimide), 8.01 (dd, 2H,
J = 8 Hz, J = 4 Hz, H4,7-phthalimide). 13CNMR (DMSO-
d6, 62.5 MHz) d: 115.7 (d, C3), 121.0 (d, C1), 124.1 (C5),
124.9 (C4,7), 129.1 (d, C4), 129.6 (d, C6), 133.7 (C3a,7a),
136.1 (C5,6), 158.3 (d, C2), 166.7 (C=O). Elemental anal.
for C14H8FNO2, Calculated: C, 69.71; H, 3.34; N, 5.81; O,
13.27. Found: C, 69.75; H, 3.31; N, 5.89; O, 13.25.
2-(3-Fluorophenyl)isoindoline-1,3-dione (3f)
2-(3-Nitrophenyl)isoindoline-1,3-dione (3i)
m.p: 199 °C, Yield: 49 %, MW: 291 g/mol, white powder,
IR (KBr, cm-1) t: 3074 (C–H, stretch, aromatic), 3032 (C–
H, stretch, aromatic), 1712 (C=O, stretch), 1597 (C=C,
m.p: 239 °C, Yield: 36 %, MW: 268 g/mol, yellow pow-
der, IR (KBr, cm-1) t: 3097 (C–H, stretch, aromatic), 1724
(C=O, stretch), 1535 (NO2, stretch, asymmetric), 1350
1
stretch, aromatic), 1492 (C=C, stretch, aromatic). HNMR
1
(CDCl3, 400 MHz) d: 7.15 (t, 1H, J = 8 Hz, H5-3-fluoro-
phenyl), 7.27 (t, 1H, H6-3-fluorophenyl), 7.32 (d, 1H,
J = 8 Hz, H2-3-fluorophenyl), 7.51 (q, 1H, J = 8 Hz, H4-
(NO2, stretch, symmetric). HNMR (CDCl3, 400 MHz) d:
7.73 (t, 1H, J = 8 Hz, H5-3-nitrophenyl), 7.88 (dd, 2H,
J = 8 Hz, J = 4 Hz, H5,6-phthalimide), 7.91 (d, 1H,
J = 8 Hz, H6-3-nitrophenyl), 8.04 (dd, J = 8 Hz,
J = 4 Hz, H5,6-phthalimide), 8.30 (d, 1H, J = 8 Hz, H4-3-
nitrophenyl), 8.47 (s, 1H, H2-3-nitrophenyl). 13CNMR
(DMSO-d6, 62.5 MHz) d: 113.6 (C2), 117.9 (C4), 122.7
(C4,7), 127.9 (C6), 129.7 (C5), 131.6 (C3a,7a), 135.0 (C5,6),
138.2 (C1), 148.03 (C3), 167 (C=O). Elemental anal. for
C14H8N2O4, Calculated: C, 62.69; H, 3.01; N, 10.44; O,
23.86. Found: C, 62.74; H, 3.09; N, 10.39; O, 23.82.
3-fluorophenyl), 7.85 (dd, 2H, J = 8 Hz, J = 4 Hz, H5,6
-
phthalimide), 8.00 (dd, 2H, J = 8 Hz, J = 4 Hz, H4,7
-
phthalimide). 13CNMR (DMSO-d6, 62.5 MHz) d: 103.7 (d,
C2), 110.5 (C6), 113.2 (C4), 123.6 (C4,7), 128.2 (d, C5),
132.3 (C3a,7a), 135.1 (C5,6), 143.5 (d, C1), 162.5 (C3), 165.8
(C=O). MS (m/z, %): 241 (M?, 100), 197 (75), 170 (20),
149 (12), 123 (15), 104 (15), 76 (30). Elemental anal. for
C14H8FNO2, Calculated: C, 69.71; H, 3.34; N, 5.81; O,
13.27. Found: C, 69.61; H, 3.29; N, 5.86; O, 13.21.
2-(4-Nitrophenyl)isoindoline-1,3-dione (3j)
2-(4-Fluorophenyl)isoindoline-1,3-dione (3g)
m.p: 265 °C, Yield: 21 %, MW: 268 g/mol, yellow pow-
der, IR (KBr, cm-1) t: 3120 (C–H, stretch, aromatic), 1708
(C=O, stretch), 1597 (C=C, Stretch, aromatic), 1525 (NO2,
stretch, asymmetric), 1346 (NO2, stretch, symmetric).
1HNMR (CDCl3, 400 MHz) d: 7.62 (d, 1H, J = 8 Hz,
m.p: 161 °C, Yield: 70 %, MW: 291 g/mol, white powder,
IR (KBr, cm-1) t: 3066 (C–H, stretch, aromatic), 1716
(C=O, stretch), 1604 (C=C, stretch, aromatic), 1465 (C=C,
1
stretch, aromatic). HNMR (CDCl3, 400 MHz) d: 7.23 (t,
2H, J = 8 Hz,
H
2,6-4-fluorophenyl), 7. 46 (q, 2H,
H
2,6-4-nitrophenyl), 7.78 (dd, 2H, J = 8 Hz, J = 4 Hz,
J = 4 Hz, H3,5-4-fluorophenyl), 7.83 (dd, 2H, J = 8 Hz,
J = 4 Hz, H5,6-phthalimide), 7.99 (dd, 2H, J = 8 Hz,
H
5,6-phthalimide), 7.91 (dd, 2H, J = 8 Hz, J = 4 Hz, H4,7
-
phthalimide), 8.21 (d, 1H, J = 8 Hz, H3,5-4-nitrophenyl).
13CNMR (DMSO-d6, 62.5 MHz) d: 117.9 (C2,6), 124.1
(C4,7), 126.5 (C3,5), 132.2 (C3a,7a), 135.4 (C5,6), 138.7 (C1),
145.7 (C4-4-nitrophenyl), 166.7 (C=O). Elemental anal. for
J = 4 Hz,
H
4,7-phthalimide). 13CNMR (DMSO-d6,
62.5 MHz) d: 116.2 (d, C3,5), 123.8 (C4,7), 127.6 (C1),
128.4 (d, C2,6), 131.7 (C3a,7a), 134.5 (C5,6), 162.0 (d, C4),
123