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6.5.4. (2E)-3-(4-Methoxyphenyl)-1-pyrrol-1-yl-2-
propen-1-one (1d). Colorless solid; IR (KBr) n 1687,
(m, 2H); 13C NMR (CDCl3) d 162.8, 150.9, 145.2, 133.1,
119.1, 116.6, 113.2, 113.0, 112.7; ESIMS: m/z 210
[M+Na]+; HRMS (FAB) m/z calcd for C11H10O2N
[M+H]+: 188.0711; found: 188.0716.
1625, 1603, 1512, 1466, 1248 cmꢀ1 1H NMR (CDCl3)
;
d 7.94 (d, J¼15.3 Hz, 1H), 7.57 (d, J¼8.5 Hz, 2H), 7.45
(br s, 2H), 6.99 (d, J¼15.3 Hz, 1H), 6.93 (d, J¼8.5 Hz,
2H), 6.33 (br s, 2H), 3.85 (s, 3H); 13C NMR (CDCl3)
d 163.2, 161.9, 147.3, 130.2, 127.0, 119.2, 114.4, 113.0,
55.4; ESIMS: m/z 250 [M+Na]+; HRMS (FAB) m/z calcd
for C14H14O2N [M+H]+: 228.1024; found: 228.1020.
6.5.11. (2E)-1-Pyrrol-1-yl-3-(2-thienyl)-2-propen-1-one
(1k). Colorless solid; IR (KBr) n 1686, 1609, 1466 cmꢀ1
;
1H NMR (CDCl3) d 8.10 (d, J¼15.0 Hz, 1H), 7.43–7.47
(m, 3H), 7.37 (d, J¼3.4 Hz, 1H), 7.10 (dd, J¼3.4, 4.5 Hz,
1H), 6.92 (d, J¼15.0 Hz, 1H), 6.34–6.38 (m, 2H); 13C
NMR (CDCl3) d 162.7, 139.8, 139.5, 132.4, 129.3, 128.4,
119.1, 114.2, 113.3; ESIMS: m/z 226 [M+Na]+; HRMS
(FAB) m/z calcd for C11H10ONS [M+H]+: 204.0483; found:
204.0489.
6.5.5. (2E)-3-(4-Bromophenyl)-1-pyrrol-1-yl-2-propen-
1-one (1e). Colorless solid; IR (KBr) n 2922, 1685, 1622,
1
1471 cmꢀ1; H NMR (CDCl3) d 7.92 (d, J¼15.6 Hz, 1H),
7.45–7.59 (m, 6H), 7.13 (d, J¼15.6 Hz, 1H), 6.36–6.38
(m, 2H); 13C NMR (CDCl3) d 162.7, 146.1, 133.1, 132.3,
129.8, 125.3, 119.2, 116.3, 113.5; ESIMS: m/z 298, 300
[M+Na]+; HRMS (FAB) m/z calcd for C13H11ONBr
[M+H]+: 276.0014; found: 276.0019.
6.5.12. (2E)-3-(4-Pyridyl)-1-pyrrol-1-yl-2-propen-1-one
(1l). Colorless solid; IR (KBr) n 1687, 1466 cmꢀ1 1H
;
NMR (CDCl3) d 8.70 (d, J¼4.9 Hz, 1H), 7.87 (d, J¼
15.5 Hz, 1H), 7.43–7.46 (m, 4H), 7.29 (d, J¼15.5 Hz, 1H),
6.36–6.38 (m, 2H); 13C NMR (CDCl3) d 162.0, 150.7,
144.4, 141.2, 121.9, 120.3, 119.2, 113.9; ESIMS: m/z 199
[M+H]+; HRMS (FAB) m/z calcd for C12H11ON2 [M+H]+:
199.0871; found: 199.0871.
6.5.6. (2E)-3-(4-Chlorophenyl)-1-pyrrol-1-yl-2-propen-
1-one (1f). Colorless solid; IR (KBr) n 1674, 1620, 1469,
1352, 1255 cmꢀ1; 1H NMR (CDCl3) d 7.87 (d, J¼15.6 Hz,
1H), 7.49 (d, J¼8.6 Hz, 2H), 7.39 (dd, J¼2.5, 2.2 Hz, 2H),
7.34 (d, J¼8.6 Hz, 2H), 7.04 (d, J¼15.6 Hz, 1H), 6.30 (dd,
J¼2.5, 2.2 Hz, 2H); 13C NMR (CDCl3) d 162.6, 146.0,
136.9, 132.7, 129.6, 129.3, 119.2, 116.2, 113.5; ESIMS:
m/z 254 [M+Na]+; HRMS (FAB) m/z calcd for
C13H11ONCl [M+H]+: 232.0529; found: 232.0529.
6.5.13. (2E)-4,4-Dimethyl-5-phenyl-1-pyrrol-1-yl-2-
penten-1-one (1m). IR (KBr) n 2956, 1682, 1629, 1469,
1
1349, 1297 cmꢀ1; H NMR (CDCl3) d 7.05–7.38 (m, 8H),
6.25–6.29 (m, 3H), 2.71 (s, 2H), 1.12 (s, 6H); 13C NMR
(CDCl3) d 163.0, 160.7, 137.4, 130.4, 130.2, 128.1, 127.9,
126.4, 119.2, 116.3, 113.1, 48.5, 38.5, 26.1; ESIMS: m/z
276 [M+Na]+; HRMS (FAB) m/z calcd for C17H20ON
[M+H]+: 254.1545; found: 254.1542.
6.5.7. (2E)-3-(3-Chlorophenyl)-1-pyrrol-1-yl-2-propen-
1-one (1g). Colorless solid; IR (KBr) n 1685, 1623,
1
1466 cmꢀ1; H NMR (CDCl3) d 7.90 (d, J¼15.6 Hz, 1H),
7.60 (s, 1H), 7.35–7.49 (m, 5H), 7.14 (d, J¼15.6 Hz, 1H),
6.36–6.39 (m, 2H); 13C NMR (CDCl3) d 162.5, 145.8,
136.0, 135.0, 130.7, 130.3, 127.9, 126.8, 119.2, 117.1,
113.6; ESIMS: m/z 254, 256 [M+Na]+; HRMS (FAB) m/z
calcd for C13H11ONCl [M+H]+: 232.0529; found: 232.0534.
6.5.14. (2E)-5-Benzyloxy-4,4-dimethyl-1-pyrrol-1-yl-2-
penten-1-one (1n). Pale yellow oil; IR (neat) n 2963,
2868, 1697, 1637, 1467, 1344, 1305, 1267 cmꢀ1; 1H NMR
(CDCl3) d 7.22–7.36 (m, 8H), 6.50 (d, J¼15.6 Hz, 1H),
6.29 (dd, J¼2.5, 2.2 Hz, 2H), 4.51 (s, 2H), 3.31 (s, 2H),
1.15 (s, 6H); 13C NMR (CDCl3) d 163.1, 158.8, 138.2,
128.3, 127.5, 127.4, 119.2, 117.0, 113.0, 77.9, 73.3, 38.8,
23.9; ESIMS: m/z 306 [M+Na]+; HRMS m/z calcd for
C18H21O2N [M+H]+: 284.1650; found: 284.1647.
6.5.8. (2E)-3-(2-Chlorophenyl)-1-pyrrol-1-yl-2-propen-
1-one (1h). Colorless solid; IR (KBr) n 1685, 1621, 1469,
1349, 1285 cmꢀ1; 1H NMR (CDCl3) d 8.30 (d, J¼15.6 Hz,
1H), 7.64 (d, J¼5.8 Hz, 1H), 7.39 (br s, 3H), 7.28 (m, 2H),
7.09 (d, J¼15.6 Hz, 1H), 6.30 (br s, 2H); 13C NMR
(CDCl3) d 162.5, 143.3, 135.4, 132.6, 131.5, 130.4, 127.9,
127.1, 119.3, 118.6, 113.5; ESIMS: m/z 254 [M+Na]+;
HRMS (FAB) m/z calcd for C13H11ONCl [M+H]+:
232.0529; found: 232.0526.
6.5.15. (2E)-5-Methyl-1-pyrrol-1-yl-2-hexen-1-one (1o).
Colorless liquid; IR (neat) 3150, 2958, 1697, 1641,1468,
1408, 1356, 1281, 1122, 742 cmꢀ1 1H NMR (CDCl3)
;
d 7.41 (t, J¼2.1 Hz, 2H), 7.29 (dt, J¼7.6, 15.3 Hz, 1H),
6.58 (d, J¼15.3 Hz, 1H), 6.35 (t, J¼2.1 Hz, 2H), 2.29–
2.22 (m, 2H), 1.87 (sept, J¼6.7 Hz, 1H), 1.00 (d, J¼
6.7 Hz, 6H); 13C NMR (CDCl3) d 162.7, 151.8, 120.4,
119.2, 113.1, 42.0, 27.9, 22.4; EIMS: m/z 177 [M+];
HRMS (EI) m/z calcd for C11H15NO [M+]: 177.1154; found:
177.1163.
6.5.9. (2E)-3-(1-Naphthyl)-1-pyrrol-1-yl-2-propen-1-one
(1i). Colorless solid; IR (KBr) n 1682, 1616, 1471,
1
1357 cmꢀ1; H NMR (CDCl3) d 8.76 (d, J¼15.0 Hz, 1H),
8.18 (d, J¼8.3 Hz, 1H), 7.88 (d, J¼8.3 Hz, 1H), 7.79 (d,
J¼7.0 Hz, 1H), 7.42–7.57 (m, 5H), 6.31 (br s, 2H); 13C
NMR (CDCl3) d 162.8, 144.6, 133.7, 131.7, 131.5, 131.2,
128.8, 127.1, 126.4, 125.4, 125.2, 123.3, 119.3, 118.4,
113.4, 113.2; ESIMS: m/z 270 [M+Na]+; HRMS (FAB) m/z
calcd for C17H14ON [M+H]+: 248.1075; found: 248.1077.
6.5.16. (2E)-1-Pyrrol-1-yl-2-hexen-1-one (1p). Light yel-
low liquid; IR (neat) 3149, 2961, 1698, 1641, 1468, 1355,
1
1277, 1121, 1072, 940 cmꢀ1; H NMR (CDCl3) d 7.38 (t,
J¼2.3 Hz, 2H), 7.27 (dt, J¼7.2, 15.2 Hz, 1H), 6.56 (d,
J¼15.2 Hz, 1H), 6.32 (t, J¼2.3 Hz, 2H), 2.34–2.29 (m,
2H), 1.62–1.51 (m, 2H), 0.98 (t, J¼7.5 Hz, 3H); 13C NMR
(CDCl3) d 162.8, 152.7, 119.5, 119.2, 113.1, 34.8, 21.3,
13.7; MS: m/z 163 [M+]; HRMS (EI) m/z calcd for
C10H13NO [M+]: 163.0997; found: 163.0997.
6.5.10. (2E)-3-(2-Furyl)-1-pyrrol-1-yl-2-propen-1-one
(1j). Colorless solid; IR (KBr) n 1688, 1618, 1468 cmꢀ1
;
1H NMR (CDCl3) d 7.73 (d, J¼15.3 Hz, 1H), 7.55 (br s,
1H), 7.45–7.48 (m, 2H), 7.04 (d, J¼15.3 Hz, 1H), 6.74 (d,
J¼3.1 Hz, 1H), 6.53 (dd, J¼1.9, 3.1 Hz, 1H), 6.34–6.37