Palladium on Carbon: An Efficient, Heterogeneous and Reusable Catalytic System
[21b]
2
-o-Tolylisoindole-1,3-dione (3g):
White solid; IR
8.79 (d, J=2.2 Hz, 1H), 8.64 (d, J=3.6 Hz, 1H), 7.85 (dd,
(
8
KBr): n=3088, 1723, 1620, 1497, 1463, 1381, 1226, 1112,
J=5.5, 2.9 Hz, 2H), 7.81 (m, 3H), 7.46 (dd, J=8.07–3.3 Hz,
À1
1
13
85, 771, 719 cm ; H NMR (300 MHz, CDCl ): d=7.96
1H); C NMR (75 MHz, CDCl ): d=166.75, 148.7, 147.3,
3
3
(
7
dd, J=5.5, 2.9 Hz, 2H), 7.80 (dd, J=5.5, 2.9 Hz, 2H), 7.38–
.53 (m, 3H), 7.2 (d, J=7.3 Hz, 1H), 2.21 (s, 3H); C NMR
134.76, 133.61, 131.54, 128.80, 124.01, 123.69; GC-MS: m/z
(% relative intensity)=224 (M , 100), 180 (46), 179 (32),
1
3
+
(
1
75 MHz, CDCl ): d=167.36, 136.56, 134.35, 132.01, 131.16,
104 (31), 76 (79).
2-Pyridin-2-yl-isoindole-1,3-dione (3q):
3
[
21d]
30.61, 129.46, 128.74, 126.89, 123.77, 18.05; GC-MS: m/z
White solid;
+
(
(
% relative intensity)=238 (M , 100), 191 (23), 104 (20), 76
IR (KBr): n=3057, 1780, 1708, 1586, 1466, 1381, 1112, 1084,
À1
1
45).
883, 713, 631 cm ; H NMR (500 MHz, CDCl
): d=7.98 (m,
3
[21b]
2
-(2-Methoxy-phenyl)-isoindole-1,3-dione (3h):
White
2H), 7.90 (t, J=7.5 Hz, 1H), 7.81 (m, 3H), 7.45 (d, J=3 Hz,
1H), 7.37 (t, J=6.5 Hz, 1H); C NMR (125 MHz, CDCl ):
3
d=166.6, 149, 146, 138, 135, 131, 123, 146; GC-MS: m/z (%
relative intensity)=224(35), 196 (100), 168 (14), 104 (32), 76
1
3
solid; IR (KBr): n=3463, 1780, 1597, 1469, 1384, 1118, 886,
À1
1
7
2
1
79, 714 cm ; H NMR (500 MHz, CDCl ): d=7.94 (m,
3
H), 7.78 (m, 2H), 7.44 (t, J=7, 1H), 7.26 (m, J=3, 8 Hz,
1
3
(
63), 50 (23).
-Quinoline-3-yl-isoindole-1,3-dione
solid; IR (KBr): n=3020, 1773, 1711, 1607, 1492, 1464, 1392,
H), 7.06 (m, J=8 Hz, 2H), 3.79 (s, 3H); C NMR
[21e]
2
(3r):
White
(
1
125 MHz, CDCl ): d=167, 155, 134, 132, 130, 129, 123, 121,
3
+
20, 112, 55; GC-MS: m/z (% relative intensity)=253 (M ,
À1
1
1
102, 1085, 876, 786, 756 cm ; H NMR (300 MHz, CDCl ):
1
00), 235 (38), 224 (16), 180 (18), 179 (33), 130 (13), 76 (61).
3
[
9]
d=9.06 (d, J=2.6 Hz, 1H), 8.32 (d, J=2.2 Hz, 1H), 8.18 (d,
J=8.8 Hz, 1H), 8.02 (dd, J=5.5, 3 Hz, 2H), 7.92–7.76 (m,
2
-(4-Acetyl-phenyl)-isoindole-1,3-dione
(3j):
Pale
yellow solid; IR (KBr): n=2919, 1713, 1601, 1513, 1386,
1
(
1
3
À1
1
4
H), 7.42 (t, J=7.3 Hz, 1H); C NMR (75 MHz, CDCl ):
225, 829, 718 cm ; H NMR (500 MHz, CDCl ): d=8.11
3
3
d=167.02, 148.02, 146.96, 134.82, 132.60, 131.61, 130.18,
29.40, 128.11, 127.64, 127.38, 125.61, 124.06.
d, J=8.5 Hz, 2H), 7.98 (dd, J=5, 3 Hz, 2H), 7.82 (dd, J=
, 3 Hz, 2H), 7.63 (d, J=8.5 Hz, 2H), 2.64 (s, 3H);
1
5
[
21f]
13
2-Thiazol-2-yl-isoindol-1,3-dione (3s):
White solid;
C NMR (125 MHz, CDCl ): d=197, 166, 136, 135, 134,
3
IR (KBr): n=3081, 1736, 1620, 1506, 1450, 1331, 1187, 883,
1
2
31, 129, 126, 123, 26; GC-MS: m/z (% relative intensity)=
À1
1
+
749, 714 cm ; H NMR (300 MHz, CDCl ): d=8.05 (dd, J=
65 (M , 30), 250 (100), 222 (31), 166 (12), 104 (20), 76 (26).
3
[18]
5.5, 2.9 Hz, 2H), 7.85 (dd, J=5.5, 2.9 Hz, 2H), 7.83 (d, J=
2
-Cyclohexylisoindole-1,3-dione (3k): White solid; IR
3
.5 Hz, 1H), 7.33 (d, J=3.6, 1H); GC-MS: m/z (% relative
(
KBr): n=3454, 2928, 2855, 1761, 1708, 1613, 1376, 1169,
+
À1
1
intensity)=230 (M , 100), 76 (41), 50 (13).
1
7
4
2
086, 1018, 903, 714 cm ; H NMR (300 MHz, CDCl ): d=
3
2
3t):
-(5-Methylfuran-2-ylmethyl)-isoindole-1,3-dione
.81 (dd, J=5.5, 3.0 Hz, 2H), 7.69 (dd, J=5.5, 3.3 Hz, 2H),
.16–4.05 (m, 1H), 2.22–2.18 (m, 2H), 1.87 (d, J=12.46,
[18]
(
Pale yellow solid; IR (KBr): n=3086, 1772, 1616,
1
À1
1
3
1566, 1396, 1334, 1187, 1052, 914, 719, 529 cm ; H NMR
H), 1.74–1.71 (m, 3H), 1.25–1.44 (m, 3H); C NMR
(500 MHz, CDCl ): d=7.86 (dd, J=5.5, 3.0 Hz, 2H), 7.71
3
(75 MHz, CDCl ): d=168.52, 133.80, 132.10, 123.05, 50.90,
3
(
dd, J=5.5, 3.0 Hz, 2H), 6.23 (d, J=3 Hz, 1H), 5.87 (d, J=
2
9.91, 26.06, 25.1; GC-MS: m/z (% relative intensity)=229
1
3
+
2.1 Hz, 1H), 4.79 (s, 2H), 2.24 (s, 3H); C NMR (125 MHz,
(
(
M , 36), 186 (34), 148 (100), 160 (10), 130 (41), 104 (14), 76
17).
CDCl ): d=167.5, 152, 147, 133.9, 132, 123, 109, 106, 34,
3
+
[
18]
13.4; GC-MS: m/z (% relative intensity)=241 (M , 100),
2
-Benzyl-isoindole-1,3-dione (3m):
White solid; IR
2
26 (18), 198 (70), 170 (26), 95 (39), 78 (56).
(
KBr): n=3455, 2958, 1742, 1706, 1655, 1369, 1169, 1086,
À1
1
1
018, 908, 716 cm ; H NMR (500 MHz, CDCl ): d=7.84
3
(
2
dd, J=5.5, 2.9 Hz, 2H), 7.70 (m, 2H), 7.43 (d, J=7.5 Hz,
H), 7.30 (m, 3H), 4.84 (s, 2H); C NMR (125 MHz,
1
3
Acknowledgements
CDCl ): d=168, 136, 134, 132, 128, 127.7, 127, 123, 41; GC-
MS: m/z (% relative intensity)=237 (M , 100), 219 (45),
3
+
The author (M.V.K) is greatly thankful to UGC (University
Grant Commission, India) for providing a Junior Research
Fellowship.
2
08 (26), 104 (62), 91 (15), 77 (38).
-tert-Butyl-isoindole-1,3-dione
liquid; IR (neat): n=2976, 1772, 1709, 1467, 1370, 1316,
[21c]
2
(3n):
Colourless
À1
1
1
7
1
1
213, 1101, 908, 750 cm ; H NMR (300 MHz, CDCl ): d=
3
.76 (dd, J=5.5, 2.9 Hz, 2H), 7.66 (dd, J=5.2, 2.9 Hz, 2H),
13
.7 (s, 9H); C NMR (75 MHz, CDCl ): d=169.74, 133.72,
3
References
32.19, 122.63, 57.88, 29; GC-MS: m/z (% relative intensi-
+
ty)=203 (M , 25), 188 (100), 148 (73), 130 (82), 102 (16), 76
[1] a) J. Balzarini, E. D. Clercq, B. Kaminska, A. Orzeszko,
Antiviral Chem. Chemother. 2003, 14, 139–144; b) A. A.
Abdel-Hafez, Arch. Pharm. Res. 2004, 27, 495–501;
c) X. B. Meng, D. Han, S. N. Zhang, W. Guo, J. R. Cui,
Z.-J. Li, Carbohydr. Res. 2007, 342, 1169–1174; d) R.
Antune, H. Buttista, R. M. Strivastuva, Bioorg. Med.
Chem. Lett. 1998, 8, 3071–3076.
[2] W. D. Figg, S. Raje, K. S. Bauer, A. Tompkins, D.
Venzon, R. Bergan, A. Chen, M. Hamilton, J. Pluda, E.
Reed, J. Pharm. Sci. 1999, 88, 121–125.
(
20), 50 (13).
-Butyl-isoindole-1,3-dione (3o):
IR (neat): n=3324, 2921, 1770, 1701, 1420, 1345, 1307, 1185,
[
21c]
2
Colourless liquid;
À1
1
1
094, 967, 709 cm ; H NMR (500 MHz, CDCl ): d=7.82
3
(
m, 2H), 7.69 (m, 2H), 3.67 (t, J=7.5 Hz, 2H), 1.64 (qt, J=
7
3
3
3
.5 Hz, 2H), 1.34 (qt, J=7.5 Hz, 2H), 0.92 (t, J=7.5 Hz,
13
H); C NMR (125 MHz, CDCl ): d=168, 134, 132, 123,
3
+
7, 30, 19, 13; GC-MS: m/z (% relative intensity)=203 (M ,
8), 161 (48), 160 (100), 133 (14), 130 (20), 105 (14), 77 (26).
[21d]
2
-pyridin-3-yl-isoindole-1,3-dione (3p):
White solid;
[3] a) E. Atra, E. I. Sato, Clin. Exp. Rheumatol. 1993, 11,
487–493; b) H. Miyachi, A. Azuma, A. Ogasawara, E.
Uchimura, N. Watanabe, Y. Kobayashi, F. Kato, M.
IR (KBr): 3029, 1784, 1709, 1612, 1482, 1430, 1387, 1228,
À1
1
1
109, 880, 794, 722 cm ; H NMR (300 MHz, CDCl ): d=
3
Adv. Synth. Catal. 2011, 353, 3415 – 3422
ꢀ 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3421