J. Wan et al. / Tetrahedron 63 (2007) 9338–9344
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4.3.4. 2-(2-Chloro-acetyl)-2,3-dihydro-isoindol-1-one
(4j). To obtain this product, the rest of the components and
catalyst must be mixed and stirred under room temperature
for 5 min before adding the substrate 2-chloro-acetamide.
Yellow crystals, mp: 135–136 ꢁC; 1H NMR (500 MHz,
CDCl3): d 7.54–7.94 (4H, m), 4.91 (2H, s), 4.88 (2H, s);
13C NMR (125 MHz, CDCl3): d 168.0, 167.2, 141.7,
134.8, 131.5, 129.1, 125.7, 123.8, 48.6, 45.2; IR (KBr,
cmꢂ1): 2955, 1721, 1613, 1464, 1450, 1403, 744; HRMS:
calcd for C10H8ClNO2Na (M+Na)+: 232.0136; found:
232.0134.
temperature was required for all benzamide reactions carried
out in our laboratory.
4.4.1. 2-Benzoyl-2,3-dihydro-isoindol-1-one (4p). Color-
less crystals, mp: 137–140 ꢁC; 1H NMR (500 MHz,
CDCl3): d 7.45–7.88 (9H, m), 5.05 (2H, s); 13C NMR
(125 MHz, CDCl3): d 170.6, 167.1, 141.6, 134.7, 134.4,
132.0, 131.3, 129.0, 128.9, 128.0, 125.5, 123.7, 49.0; IR
(KBr, cmꢂ1): 2946, 1732, 1671, 1616, 1599, 1496, 1470,
1441, 733; HRMS: calcd for C15H11NO2Na (M+Na)+:
260.0682; found: 260.0675.
4.3.5. 3-Oxo-3-(1-oxo-1,3-dihydro-isoindol-2-yl)-propio-
4.4.2. 2-(4-Fluoro-benzoyl)-2,3-dihydro-isoindol-1-one
(4q). Colorless crystals, mp: 148–150 ꢁC; 1H NMR
1
nitrile (4k). Colorless crystals, mp: 214–216 ꢁC; H NMR
(500 MHz, CDCl3): d 7.55–8.00 (4H, m), 4.90 (2H, s),
4.31 (2H, s); 13C NMR (125 MHz, CDCl3): d 168.0, 162.6,
141.4, 135.3, 130.2, 129.4, 125.9, 123.9, 113.5, 48.6, 28.4;
IR (KBr, cmꢂ1): 2959, 2252, 1731, 1704, 1614, 1464,
1453, 1382, 741; HRMS: calcd for C11H8N2O2Na
(M+Na)+: 223.0478; found: 223.0476.
(500 MHz, CDCl3): d 7.13–7.90 (8H, m), 5.06 (2H, s); 13
C
NMR (125 MHz, CDCl3): d 169.5, 167.2, 141.6, 134.5,
131.9, 131.8, 131.2, 129.0, 125.6, 123.7, 115.3, 115.1,
49.1; IR (KBr, cmꢂ1): 2947, 1719, 1671, 1603, 1509,
1448, 737; HRMS: calcd for C15H10FNO2Na (M+Na)+:
278.0588; found: 278.0581.
4.3.6. 2-Hexanoyl-2,3-dihydro-isoindol-1-one (4l). Color-
4.4.3. 2-(2,3-Dimethyl-benzoyl)-2,3-dihydro-isoindol-1-
one (4r). Colorless crystals, mp: 144–146 ꢁC; 1H NMR
(500 MHz, CDCl3): d 7.49–7.84 (4H, m), 7.12–7.29 (3H,
m), 5.05 (2H, s), 2.34 (3H, s), 2.24 (3H, s); 13C NMR
(125 MHz, CDCl3): d 171.2, 166.6, 141.5, 137.4, 136.6,
134.5, 133.2, 131.5, 131.3, 129.0, 125.7, 125.6, 124.1,
123.8, 48.5, 20.3, 16.6; IR (KBr, cmꢂ1): 2955, 2860, 1749,
1672, 1615, 1493, 1468, 1441, 1375, 743; HRMS: calcd
for C17H15NO2Na (M+Na)+: 288.0995; found: 288.0986.
1
less crystals, mp: 79–81 ꢁC; H NMR (500 MHz, CDCl3):
d 7.50–7.92 (4H, m), 4.82 (2H, s), 3.10 (2H, t, J¼7.5 Hz),
1.73–7.76 (2H, m, J¼7.5 Hz), 1.38–1.42 (4H, m), 0.92
(3H, t, J¼7.5 Hz); 13C NMR (125 MHz, CDCl3): d 174.7,
167.8, 141.4, 134.2, 131.7, 128.8, 125.4, 123.6, 48.4, 37.1,
31.6, 24.3, 22.7, 14.2; IR (KBr, cmꢂ1): 2954, 2929, 2848,
1713, 1695, 1615, 1467, 1440, 740; HRMS: calcd for
C14H17NO2Na (M+Na)+: 254.1151; found: 254.1145.
4.3.7. 2-Isobutyryl-2,3-dihydro-isoindol-1-one (4m). Col-
orless crystals, mp: 84–87 ꢁC; 1H NMR (500 MHz, CDCl3):
d 7.48–7.91 (4H, m), 4.81 (2H, s), 3.95 (1H, m), 1.25 (6H, d,
J¼6.5 Hz); 13C NMR (125 MHz, CDCl3): d 178.8, 167.5,
141.4, 134.2, 131.7, 128.8, 125.4, 123.6, 48.8, 34.2, 19.0;
IR (KBr, cmꢂ1): 2981, 2963, 2935, 2870, 1716, 1696,
1611, 1467, 1446, 1388, 734; HRMS: calcd for
C12H13NO2Na (M+Na)+: 226.0838; found: 226.0834.
4.4.4. 2-(3,5-Dimethoxy-benzoyl)-2,3-dihydro-isoindol-1-
one (4s). White solid, mp: 141–143 ꢁC; 1H NMR (500 MHz,
CDCl3): d 7.51–7.89 (4H, m), 6.64 (1H, t), 6.81 (2H, d), 5.04
(2H, s), 3.83 (6H, s); 13C NMR (125 MHz, CDCl3): d 170.4,
166.9, 160.5, 141.6, 136.6, 134.4, 131.3, 129.0, 125.7, 123.7,
106.7, 104.3, 55.8, 49.1; IR (KBr, cmꢂ1): 2972, 2947, 2847,
1749, 1671, 1604, 1496, 1454, 1426, 1372, 1293, 746;
HRMS: calcd for C17H15NO4Na (M+Na)+: 320.0893;
found: 320.0883.
4.3.8. 2-Acryloyl-2,3-dihydro-isoindol-1-one (4n). White
solid, mp: 114–115 ꢁC; 1H NMR (500 MHz, CDCl3):
d 7.51–7.93 (5H, m), 6.62–6.66 (1H, m), 5.95–5.97 (1H,
m), 4.90 (2H, s); 13C NMR (125 MHz, CDCl3): d 167.9,
166.2, 141.6, 134.4, 131.6, 131.4, 130.0, 128.9, 125.6,
123.7, 48.6; IR (KBr, cmꢂ1): 2918, 2852, 1732, 1672,
1614, 1473, 1446, 1411, 896, 735; HRMS: calcd for
C11H9NO2Na (M+Na)+: 210.0525; found: 210.0520.
4.5. Preparation of 10a and 10b
The preparation process followed the general conditions for
4f–o.
4.5.1. 2-Phenyl-2,3-dihydro-isoindol-1-one (10a). Color-
less crystals, mp: 164–167 ꢁC; 1H NMR (500 MHz,
CDCl3): d 7.16–7.93 (9H, m), 4.83 (2H, s); 13C NMR
(125 MHz, CDCl3): d 167.8, 140.3, 139.7, 133.4, 132.2,
129.3, 128.5, 124.6, 124.3, 122.8, 120.0, 50.9; IR (KBr,
cmꢂ1): 3026, 2922, 2851, 1686, 1595, 1501, 1465, 1440,
732; HRMS: calcd for C14H11NONa (M+Na)+: 232.0733;
found: 232.0726.
4.3.9. 2-Phenylacetyl-2,3-dihydro-isoindol-1-one (4o).
1
Colorless crystals, mp: 139–140 ꢁC; H NMR (500 MHz,
CDCl3): d 7.20–7.88 (9H, m), 4.78 (2H, s), 4.42 (2H, s);
13C NMR (125 MHz, CDCl3): d 172.3, 167.8, 141.5,
134.4, 131.6, 130.0, 128.9, 128.8, 127.3, 125.6, 123.7,
48.7, 43.1; IR (KBr, cmꢂ1): 2923, 2851, 1719, 1705, 1619,
1498, 1462, 1446, 735; HRMS: calcd for C16H13NO2Na
(M+Na)+: 274.0838; found: 274.0835.
4.5.2. 2-Isopropyl-2,3-dihydro-isoindol-1-one (10b). Col-
orless crystals, mp: 82–84 ꢁC; 1H NMR (500 MHz,
CDCl3): d 7.41–7.83 (4H, m), 4.67 (1H, m, J1,2¼7 Hz),
4.33 (2H, s), 1.28 (6H, d, J2,1¼7 Hz); 13C NMR (125 MHz,
CDCl3): d 168.0, 141.4, 133.6, 131.2, 128.1, 123.4, 122.9,
45.2, 42.8, 21.0; IR (KBr, cmꢂ1): 2975, 2929, 2864, 1672,
1591, 1471, 1461, 1411, 1386, 740; HRMS: calcd for
C11H13NONa (M+Na)+: 198.0889; found: 198.0884.
4.4. Representative procedure for the TMSCl catalyzed
reactions of o-phthalaldehyde and benzamides
Identical conditions adopted as in the above aliphatic am-
ides’reactions caused ideal results in this section, but a reflux