Zou ZQ, et al. Sci China Chem January (2012) Vol.55 No.1
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13C NMR (101 MHz, CDCl3) : 149.26, 148.63, 130.65,
121.03, 119.61, 111.26, 110.47, 108.48, 55.97, 55.87, 53.13;
Calcd. HRMS for C13H16NO2 (M+H), 218.1181; Found,
218.1181.
7.92 Hz), 7.36 (1H, d, J = 7.65 Hz), 6.70 (2H, d, J = 1.83
Hz), 6.22 (2H, t, J = 1.81 Hz), 5.16 (2H, s); 13C NMR (101
MHz, CDCl3) : 148.55, 140.59, 132.87, 129.87, 122.74,
121.78, 121.16, 109.42, 52.48; Calcd. HRMS for
C11H11N2O2 (M+H), 203.0821; Found, 203.0818.
N-(3,4,5-Trimethoxybenzyl)-1H-pyrrole (1h): 1.18 g, white
1
solid, yield: 96%; mp: 54.8–54.9 °C; H NMR (400 MHz,
N-(4-Cyanobenzyl)-1H-pyrrole (1n): 0.87 g, white solid,
yield: 96%; mp: 48.3–48.4 °C; 1H NMR (400 MHz, CDCl3)
: 7.58 (2H, d, J = 8.26 Hz), 7.13 (2H, d, J = 8.24 Hz), 6.67
(2H, t, J = 1.98 Hz), 6.22 (2H, t, J = 2.01 Hz), 5.12 (2H, s);
13C NMR (101 MHz, CDCl3) : 143.85, 132.59, 127.32,
121.28, 118.64, 109.30, 52.78; Calcd. HRMS for C12H11N2
(M+H), 183.0922; Found, 183.0922.
CDCl3) : 6.74 (2H, t, J = 1.97 Hz), 6.38 (2H, s), 6.24 (2H,
t, J = 2.01 Hz), 5.03 (2H, s), 3.87 (3H, s), 3.83 (6 H, s); 13C
NMR (101 MHz, CDCl3) : 153.52, 137.41, 133.94, 121.19,
108.61, 104.08, 60.85, 56.08, 53.47; Calcd. HRMS for
C14H18NO3 (M+H), 248.1287; Found, 248.1286.
N-(3-Methoxy-4-hydroxybenzyl)-1H-pyrrole (1i): 0.90 g,
1
white solid, yield: 97%; mp: 54.7–55.1 °C; H NMR (400
N-(2-Cyanobenzyl)-1H-pyrrole (1o): 0.83 g, yellow oil,
yield: 91%; 1H NMR (400 MHz, CDCl3) : 7.63 (1H, d, J =
7.60 Hz), 7.49 (1H, t, J = 7.67, 7.67 Hz), 7.35 (1H, t, J =
7.60 Hz), 6.96 (1H, d, J = 7.84 Hz), 6.71 (2H, m), 6.20 (2H,
m), 5.24 (2H, s); 13C NMR (101 MHz, CDCl3) : 142.04,
133.50, 132.88, 128.28, 127.98, 121.35, 117.22, 110.90,
109.31, 51.30; Calcd. HRMS for C12H11N2 (M+H),
183.0922; Found, 183.0920.
MHz, CDCl3) : 6.95 (1H, d, J = 8.06 Hz), 6.77 (3H, m),
6.70 (1H, s), 6.27 (2H, t, J = 1.95 Hz), 5.75 (1H, s), 5.05
(2H, s), 3.88 (3H, s); 13C NMR (101 MHz, CDCl3) :
146.86, 145.28, 130.02, 121.05, 120.46, 114.52, 109.93,
108.48, 55.95, 53.26; Calcd. HRMS for C12H14NO2 (M+H),
204.1025; Found, 204.1022.
N-(3-Hydroxy-4-methoxybenzyl)-1H-pyrrole (1j): 0.89 g,
1
white solid, yield: 88%; mp: 70.5–70.9 °C; H NMR (400
N-(Pyridinyl-2-methyl)-1H-pyrrole (1p): 0.72 g, colorless
oil, yield: 91%; 1H NMR (400 MHz, CDCl3) : 8.59 (1H, d,
J = 4.57 Hz), 7.63 (1H, dd, J = 10.93, 4.44 Hz), 7.20 (1H,
m), 6.82 (1H, d, J = 7.87 Hz), 6.77 (2H, s), 6.26 (2H, s),
5.23 (2H, s); 13C NMR (101 MHz, CDCl3) : 158.40,
149.26, 137.18, 122.45, 121.40, 120.82, 108.99, 55.17;
Calcd. HRMS for C10H11N2 (M+H), 159.0922; Found,
159.0920.
MHz, CDCl3) : 6.86 (1H, d, J = 8.23 Hz), 6.84 (1H, d, J =
1.88 Hz), 6.76 (2H, t, J = 1.95 Hz), 6.71 (1H, dd, J = 8.19,
1.81 Hz), 6.27 (2H, t, J = 2.00 Hz), 5.78 (1H, s), 5.02 (3H,
s), 3.92 (3H, s); 13C NMR (101 MHz, CDCl3) : 146.21,
145.88, 131.49, 121.06, 118.92, 113.76, 110.84, 108.46,
56.08, 53.00; Calcd. HRMS for C12H14NO2 (M+H),
204.1025; Found, 204.1023.
N-(Thienyl-2-methyl)-1H-pyrrole (1q): 0.76 g, white solid,
yield: 93%; mp: 39.1–39.8 °C; 1H NMR (400 MHz, CDCl3)
: 7.31 (1H, d, J = 4.86 Hz), 7.03 (2H, dd, J = 7.98, 2.90
Hz), 6.81 (2H, s), 6.27 (2H, s), 5.28 (2H, s); 13C NMR (101
MHz, CDCl3) : 140.69, 126.98, 126.05, 125.63, 120.75,
108.78, 48.09; Calcd. HRMS for C9H10NS (M+H),
164.0534; Found, 164.0533.
N-(2-Fluorobenzyl)-1H-pyrrole (1k): 0.67 g, colorless oil,
yield: 76%; H NMR (400 MHz, CDCl3) : 7.31 (1H, m),
1
7.13 (2H, m), 7.01 (1H, t, J = 7.33 Hz), 6.78 (2 H, s), 6.26
(2H, s), 5.18 (2H, s); 13C NMR (101 MHz, CDCl3) :
160.24 (1C, d, J = 246.72 Hz), 129.54 (1C, d, J = 8.05 Hz),
129.23 (1C, d, J = 3.79 Hz), 125.49 (1C, d, J = 14.72 Hz),
124.50 (1C, d, J = 3.61 Hz), 121.18 (2C, s), 115.40 (1 C, d,
J = 21.22 Hz), 108.71 (2 C, s), 46.99 (1C, d, J = 4.59 Hz);
Calcd. HRMS for C11H11FN (M+H), 176.0876; Found,
176.0868.
N-(Furan-2-ylmethyl)-1H-pyrrole (1r): 0.76 g, colorless
oil, yield: 71%; 1H NMR (400 MHz, CDCl3) : 7.50 (1H, s),
6.86 (2H, s), 6.47 (1H, s), 6.38 (1H, d, J = 2.46 Hz), 6.34
(2H, s), 5.13 (2H, s); 13C NMR (101 MHz, CDCl3) :
151.00, 142.82, 120.85, 110.57, 108.72, 108.27, 46.15;
Calcd. HRMS for C9H10NO (M+H), 148.0762; Found,
148.0766.
N-(4-Nitrobenzyl)-1H-pyrrole (1l): 1.0 g, yellowish solid,
1
yield: 99%; mp: 59.9–60 °C; H NMR (400 MHz, CDCl3)
: 8.17 (2H, d, J = 8.67 Hz), 7.20 (2H, d, J = 8.57 Hz), 6.70
(2H, t, J = 1.97, 1.97 Hz), 6.25 (2H, t, J = 1.99, 1.99 Hz),
5.19 (2H, s); 13C NMR (101 MHz, CDCl3) : 147.46,
145.76, 127.38, 124.02, 121.26, 109.41, 52.56; Calcd.
HRMS for C11H11N2O2 (M+H), 203.0821; Found, 203.0820.
N-Cinnamyl-1H-pyrrole (1s): 0.68 g, yellow liquid, yield:
1
74%; H NMR (400 MHz, CDCl3) : 7.27 (5H, m), 6.68 (2
H, s), 6.44 (1H, d, J = 15.83 Hz), 6.28 (1H, td, J = 15.77,
6.10 Hz), 6.18 (2H, s), 4.58 (2H, d, J = 6.00 Hz); 13C NMR
(101 MHz, CDCl3) : 136.34, 132.60, 128.67, 127.96,
126.58, 125.57, 120.70, 108.49, 51.62; Calcd. HRMS for
N-(3-Nitrobenzyl)-1H-pyrrole (1m): 0.92 g, yellow solid,
yield: 91%; mp: 40.8–41 °C; H NMR (400 MHz, CDCl3)
: 8.10 (1H, d, J = 8.06 Hz), 7.95 (1H, s), 7.47 (1H, t, J =
1