Solid-Phase Synthesis of 2-Alkenamides
J. Chin. Chem. Soc., Vol. 51, No. 6, 2004 1305
mmol) in anhydrous DCE solution and then triethylamine
(1.5 mmol). The mixture was stirred at room temperature for
2 h and the amide resin 6 was collected by filtration and
washed successively with 3% HCl (10 ´ 3 mL), H2O (10 ´ 3
mL) and THF (5 ´ 3 mL). The resin 6 was then suspended in
CH2Cl2 (10 mL) and treated with 1 mL (11.6 mmol) of 30%
H2O2. After stirring for 30 min at room temperature, the re-
sidual resin was collected by filtration. The filtrate was
treated with saturated NaHCO3 (20 mL) and washed with wa-
ter, dried over magnesium sulfate and evaporated to give
products 7.
1H), 7.11-7.60 (m, 5H), 6.92 (dq, J = 15.3, 1.7 Hz, 1H), 5.92
(dq, J = 15.3, 1.7 Hz, 1H), 1.85 (dd, J = 1.7, 6.7 Hz, 3H). IR:
nmax 3442, 3029, 1696, 1600, 961 cm-1.
N-Benzyl-2-butenamide (7bd):9
Mp. 116-117 °C (lit. 116-117 C). 1H NMR: d 7.31-7.25
(m, 5H), 6.85 (dq, J = 16.5, 6.8 Hz, 1H), 5.91-5.80 (m, 1H),
5.80 (dq, J = 16.5, 1.6 Hz, 1H), 4.50 (d, J = 5.8 Hz, 2H), 1.83
(dd, J = 1.6, 6.8 Hz, 3H). IR: nmax 3454, 3035, 1684, 1650,
1506, 965 cm-1.
N-Butyl-2-butenamide (7be):9
Oil. 1H NMR: d 6.80 (dq, J = 16.5, 7.0 Hz, 1H),
5.92-5.85 (m, 1H), 5.76 (dq, J = 16.5, 1.5 Hz, 1H), 3.36-3.30
(m, 2H), 1.82 (dd, J = 1.5, 7.0 Hz, 3H), 1.52-1.35 (m, 4H),
0.92 (t, J = 7.0 Hz, 3H). IR: nmax 3456, 2951, 1675, 1630,
1512, 1455, 915 cm-1.
N-Phenylacrylamide (7aa):9
Mp. 102-104 °C (lit. 101-103 °C).1H NMR: d 8.04 (bs,
1H), 7.10-7.61 (m, 5H), 6.40 (dd, J = 17.0, 2.0 Hz, 1H), 6.32
(dd, J = 17.0, 10.0 Hz, 1H), 5.70 (dd, J = 10.0, 2.0 Hz, 1H).
IR: nmax 3442, 3029, 1695, 1601, 962 cm-1.
N-(p-Methylphenyl)acrylamide (7ab):10
Mp. 138-139 °C (lit. 138-139 °C).1H NMR: d 7.70 (bs,
1H), 7.45 (d, J = 8.3 Hz, 2H), 7.10 (d, J = 8.3 Hz, 2H), 6.44
(dd, J = 17.1, 1.9 Hz, 1H), 6.28 (dd, J = 17.1, 10.0 Hz, 1H),
5.72 (dd, J = 10.0, 1.9 Hz, 1H), 2.30 (s, 3H). IR: nmax 3445,
3031, 1695, 1600, 1507, 1377, 960, 822 cm-1.
ACKNOWLEDGEMENTS
We are grateful for the financial support from the Natu-
ral Science Foundation of Jiangxi Province, P. R. China.
N-(p-Chlorophenyl)acrylamide (7ac):11
Mp. 100-101 °C (lit. 101-103 °C).1H NMR: d 9.89 (bs,
1H), 7.67 (d, J = 8.5 Hz, 2H), 7.28 (d, J = 8.5 Hz, 2H), 6.41-
6.27 (m, 2H), 5.70 (dd, J = 8.6, 3.6 Hz, 1H). IR: nmax 3441,
3032, 1690, 1600, 1455, 969, 820 cm-1.
Received May 21, 2003.
REFERENCES
N-Benzylacrylamide (7ad):9
Mp. 58-59 °C (lit. 58-59 °C).1H NMR: d 7.31-7.25 (m,
5H), 6.36-6.15 (m, 2H), 5.98-5.86 (m, 1H), 5.64 (dd, J = 1.7,
1.1 Hz, 1H), 4.50 (d, J = 5.8, 2.1 Hz, 2H). IR: nmax 3454, 3030,
1685, 1630, 1506, 975 cm-1.
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N-(n-Butyl)acrylamide (7ae):9
Oil. 1H NMR: d 6.30-5.98 (m, 2H), 5.80-5.90 (m, 1H),
5.60 (dd, J = 10.1, 1.0 Hz, 1H), 3.33 (q, J = 6.0 Hz, 2H),
1.52-1.35 (m, 4H), 0.92 (t, J = 7.0 Hz, 3H). IR: nmax 3456,
2951, 1675, 1630, 1512, 1455, 915 cm-1.
N,N-Diisopropylacylamide (7af):12
Oil. 1H NMR: d 6.24-5.08 (m, 2H), 5.60 (dd, J = 10.0,
1.1 Hz, 1H), 3.68 (m 2H), 1.30 (d, J = 7.1 Hz, 12H). IR: nmax
3455, 2965, 1638, 1512, 1445, 1374, 1045, 915 cm-1.
N-Acrylpiperidine (7ag):12
Oil. 1H NMR: d 6.25-6.10 (m, 2H), 5.65 (dd, J = 10.0,
1.0 Hz, 1H), 3.15 (t, J = 5.7 Hz, 4H), 1.62-1.75 (m, 4H),
1.22-1.11 (m, 2H). IR: nmax 3459, 2920, 1680, 1629, 1510,
975 cm-1.
N-Phenyl-2-butenamide (7ba):9
Mp. 110-111 °C (lit. 112-114 °C). 1H NMR: d 8.04 (bs,