Bulk and Activated Carbon-Supported Tungstophosphoric Acid
695
Spectroscopic data for the compounds from Table 4
Entry 1: νmax (KBr): 3291, 2329, 1687, 1647, 1547, 1445, 1349, 1229, 1009, 754 cm-1;
δH (CDCl3) 2.01 (3H, s, COMe), 3.41 (1H, dd, J 6.0, 16.8 Hz, CH2), 3.73 (1H, dd, J 5.2,
17.2 Hz, CH2), 5.50–5.55 (1H, m, CH), 6.74 (1H, d, J 7.2 Hz, NH), 7.25 (4H, d, J 4.4 Hz
Ph), 7.44 (2H, t, J 8.0 Hz, Ph), 7.56 (1H, t, J 7.6 Hz, Ph), 7.87 (2H, d, J 8.4 Hz, Ph);
Entry 2: ν max (KBr): 3278, 3099, 2925, 1682, 1646, 1556, 1447, 1372, 1195, 990, 750 cm-1;
δH (CDCl3) 2.01 (3H, s, COMe), 3.43 (1H, dd, J 6.0, 16.8 Hz, CH2), 3.75 (1H, dd, J 5.2,
16.8 Hz, CH2), 5.53–5.57 (1H, m, CH), 6.68 (1H, d, J 7.6 Hz, NH), 7.19–7.30 (5H, m, Ph),
7.43 (2H, t, J 8.0 Hz, Ph) 7.55 (1H, t, J 7.6 Hz, Ph), 7.88 (2H, d, J 8.0 Hz, Ph);
Entry 3: ν
(KBr): 3306, 1693, 1644, 1545, 1522, 1347, 983, 684 cm-1; δH (CDCl3)
max
2.08 (3H, s, COMe), 3.51 (1H, dd, J 5.6, 17.6 Hz, CH2), 3.79 (1H, dd, J 5.2, 17.6 Hz, CH2),
5.62–5.67 (1H, m, CH), 6.91 (1H, d, J 7.6 Hz, NH), 7.42–7.49 (3H, m, Ph), 7.57 (1H, t, J 7.6
Hz, Ph), 7.68 (1H, d, J 7.6 Hz, Ph), 7.87 (2H, d, J 7.6 Hz, Ph), 8.06 (1H, d, J 6.8 Hz, Ph),
8.19 (1H, s, Ph);
Entry 4: ν
(KBr): 3306, 1696, 1646, 1595, 1537, 1350, 988, 755 cm-1; δH (CDCl3)
max
2.10 (3H, s, COMe), 3.51 (1H, dd, J 5.6, 17.6 Hz, CH2), 3.81 (1H, dd, J 5.2, 17.6 Hz, CH2),
5.65–5.67 (1H, m, CH), 6.96 (1H, d, J 8.0 Hz, NH), 7.47 (2H, t, J 8.0 Hz, Ph), 7.51 (2H, d, J
8.8 Hz, 2H, Ph), 7.60 (1H, t, J 7.2 Hz, Ph), 7.89 (2H, d, J 7.2 Hz, Ph), 8.17 (2H, d, J 8.8 Hz,
Ph);
Entry 5: ν
(KBr): 3301, 2928, 1688, 1648, 1545, 1372, 1238, 1033, 754 cm-1; δH
max
(CDCl3) 2.0 (3H, s, COMe), 3.39 (1H, dd, J 6.4, 16.8 Hz, CH2), 3.72 (1H, dd, J 5.2, 17.2
Hz, CH2), 3.74 (3H, s OMe), 5.46–5.51 (1H, m, CH), 6.57 (1H, d, J 8.0 Hz, NH), 6.81 (2H,
d, J 8.4 Hz, Ph), 7.23 (2H, d, J 8.0 Hz, Ph), 7.42 (2H, t, J 7.6 Hz, Ph), 7.54 (1H, t, J 7.2 Hz,
Ph), 7.89 (2H, d, J 7.2 Hz, Ph);
Entry 6: ν
(KBr): 3285, 2923, 1684, 1651, 1550, 1374, 1292, 1006, 757 cm-1; δH
max
(CDCl3) 2.0 (3H, s, COMe), 2.28 (3H, s, CH3), 3.37 (1H, dd, J 6.4, 16.8 Hz, CH2), 3.71 (1H,
dd, J 5.2, 17.2 Hz, CH2), 3.75 (3H, s OMe), 5.46–5.51 (1H, m, CH), 6.57 (1H, d, J 8.0 Hz,
NH), 6.81 (2H, d, J 8.4 Hz, Ph), 7.24 (2H, d, J 8.0 Hz, Ph), 7.44 (2H, t, J 7.6 Hz, Ph), 7.53
(1H, t, J 7.2 Hz, Ph), 7.88 (2H, d, J 7.2 Hz, Ph);
Entry 7: ν
(KBr): 3329, 3049, 2961, 1747, 1717, 1643, 1528, 1451, 1371, 1037, 754
max
cm -1; δH (CDCl3) 1.99 (3H, s, COMe), 2.10 (3H, s, COMe), 3.69 (3H, s, OMe), 4.07 (1H, d, J
5.6 Hz, CH), 5.73 (1H, dd, J 5.6, 9.2 Hz, CH), 6.91 (1H, d, J 8.4 Hz, NH), 7.23–7.31 (5H, m, Ph);
Entry 8: ν
(KBr): 3324, 1744, 1714, 1646, 1541, 1486, 1371, 1091, 724 cm-1; δH
max
(CDCl3) 1.99 (3H, s, COMe), 2.13 (3H, s, COMe), 3.70 (3H, s, OMe), 4.04 (1H, d, J 5.6 Hz,
CH), 5.68 (1H, dd, J 5.6, 9.2 Hz, CH), 6.94 (1H, d, J 8.4 Hz, NH), 7.20 (2H, d, J 8.8 Hz, Ph),
7.25 (2H, d, J 8.0 Hz, Ph);
Conclusion
In conclusion, we have reported a new catalytic method for the synthesis of β-acetamido
ketones/esters using PAK, PAN and PWS as efficient, reusable and eco-friendly heterogeneous
catalysts. The advantages of this method are reusability of catalysts, easy work-up procedure and
high yields. Simple experimental procedure as well as high yield and selectivity, makes this
method useful addition to the methodologies that require green super acid solid catalyst.
References
1.
Casimir J R, Turetta C, Ettouati L and Paris J, Tetrahedron lett., 1995, 36, 4797-4800.