B.-L. Li et al. / Tetrahedron 69 (2013) 7011e7018
7015
2982, 2922, 1653, 1498, 1410, 1242, 827, 765, 698 cmꢁ1
(CDCl3, 500 MHz) 2.10 (s, 3H), 2.40 (s, 3H), 2.51 (s, 3H), 6.65 (s,1H),
7.28e7.33 (m, 6H), 7.42 (t, J¼7.5 Hz, 1H), 7.49 (t, J¼7.5 Hz, 2H) ppm;
13C NMR (CDCl3, 125 MHz)
12.9, 15.8, 31.1, 120.6, 122.5, 125.7,
126.2, 126.4, 128.1, 129.3, 129.7, 132.8, 135.3, 136.9, 138.7, 197.5 ppm;
Anal. Calcd for C20H19NOS: C, 74.73; H, 5.96; N, 4.36. Found: C,
74.90; H, 6.13; N, 4.55; ESI-MS: m/z¼322 (Mþ1)þ.
;
1H NMR
7.33e7.35 (m, 2H), 7.46 (t, J¼7.5 Hz, 1H), 7.50e7.56 (m, 3H), 7.70 (d,
d
J¼8.0 Hz, 1H), 8.16 (d, J¼8.0 Hz, 1H), 8.27 (t, J¼6.0 Hz, 2H) ppm; 13
C
NMR (CDCl3, 125 MHz)
d 13.0, 31.2, 121.5, 121.6, 122.3, 123.6, 123.9,
d
126.3, 128.5, 129.0, 129.5, 135.4, 136.0, 137.8, 138.3, 148.2,
196.7 ppm; Anal. Calcd for C19H16N2O3: C, 71.24; H, 5.03; N, 8.74.
Found: C, 71.42; H, 4.85; N, 8.93; ESI-MS: m/z¼321 (Mþ1)þ.
4.3.11. 1-(2-Methyl-5-(5-nitrophenyl)-1-phenyl-1H-pyrrol-3-yl)
4.3.5. 1-(4-(2-Fluorophenyl)-2-methyl-1-phenyl-1H-pyrrol-3-yl)
ethanone (5e). White solid (267 mg, 91%); IR (KBr): 3117, 3064,
2922, 1643, 1504, 1406, 1232, 1213, 759, 698 cmꢁ1; 1H NMR (CDCl3,
ethanone (5k). Brown sticky liquid (266 mg, 83%); IR (neat): 3132,
2922, 1653, 1541, 1516, 1419, 1340, 1224, 854, 752, 696 cmꢁ1 1H
;
NMR (CDCl3, 500 MHz)
d 2.18 (s, 3H), 2.39 (s, 3H), 6.77 (s, 1H), 7.33
500 MHz)
d
2.11 (s, 3H), 2.43 (s, 3H), 6.72 (s, 1H), 7.11e7.18 (m, 2H),
(d, J¼8.0 Hz, 2H), 7.46 (t, J¼7.5 Hz, 1H), 7.50e7.55 (m, 3H), 8.25 (d,
7.31e7.38 (m, 5H), 7.43 (t, J¼7.5 Hz, 1H), 7.32e7.33 (m, 2H), 7.42 (t,
J¼8.0 Hz, 2H) ppm; 13C NMR (CDCl3, 125 MHz)
d 12.9, 31.2, 121.7,
J¼8.0 Hz, 2H), 7.49 (t, J¼7.5 Hz, 2H) ppm; 13C NMR (CDCl3, 125 MHz)
122.5, 123.6, 125.1, 126.2, 128.6, 129.5, 129.5, 136.1, 138.3, 153.0,
156.5, 196.7 ppm; Anal. Calcd for C19H16N2O3: C, 71.24; H, 5.03; N,
8.74. Found: C, 71.40; H, 4.86; N, 8.95; ESI-MS: m/z¼321 (Mþ1)þ.
d
13.0, 30.0, 115.6 (d, 2JCF¼22.2 Hz), 118.8, 121.5, 122.7, 123.8, 123.9,
3
124.1, 124.1, 126.2, 128.2, 128.8 (d, JCF¼8.0 Hz), 129.4, 131.6 (d,
4JCF¼3.2 Hz), 135.4, 138.6, 161.0 (d, 1JCF¼244.1 Hz), 197.8 ppm; Anal.
Calcd for C19H16FNO: C, 77.80; H, 5.50; N, 4.77. Found: C, 77.98; H,
5.32; N, 4.95; ESI-MS: m/z¼294 (Mþ1)þ.
4.3.12. 1-(2-Methyl-1-phenyl-4-(3-(trifluoromethyl)phenyl)-1H-pyr-
rol-3-yl)ethanone (5l). Yellow sticky liquid (274 mg, 80%); IR (neat):
3126, 3076, 2924, 1654, 1519, 1408, 1325, 1224, 1122, 813, 767,
4.3.6. 1-(4-(2-Chlorophenyl)-2-methyl-1-phenyl-1H-pyrrol-3-yl)
ethanone (5f). White solid (275 mg, 89%); IR (KBr): 3120, 3063,
2920, 1647, 1502, 1410, 1230, 1051, 758, 696 cmꢁ1; 1H NMR (CDCl3,
500 MHz)
7.29e7.30 (m, 2H), 7.38e7.40 (m, 1H), 7.42 (t, J¼7.5 Hz, 1H),
7.45e7.50 (m, 3H) ppm; 13C NMR (CDCl3, 125 MHz)
13.2, 30.0,
121.2, 122.5, 122.8, 126.2, 126.6, 128.1, 128.6, 129.3, 129.5, 132.0,
134.4, 135.4, 135.4, 138.6, 196.5 ppm; Anal. Calcd for C19H16ClNO: C,
73.66; H, 5.21; N, 4.52. Found: C, 73.85; H, 5.03; N, 4.70; ESI-MS: m/
z¼310 (Mþ1)þ.
696 cmꢁ1; 1H NMR (CDCl3, 500 MHz)
d 2.09 (s, 3H), 2.41 (s, 3H), 6.72
(s, 1H), 7.33 (d, J¼7.0 Hz, 2H), 7.45 (t, J¼7.5 Hz, 1H), 7.48e7.51 (m,
3H), 7.56 (d, J¼8.0 Hz, 2H), 7.66 (s, 1H) ppm; 13C NMR (CDCl3,
d
2.11 (s, 3H), 2.40 (s, 3H), 6.68 (s, 1H), 7.27e7.28 (m, 2H),
125 MHz)
d
12.9, 31.1, 121.1, 122.4, 124.2 (q, 1JFC¼270.7 Hz), 123.4 (q,
3JFC¼4.0 Hz), 124.8, 125.8 (q, 3JFC¼4.0 Hz), 126.2, 128.3, 128.7, 129.4,
2
d
130.7 (q, JFC¼32.1 Hz), 132.6, 135.8, 136.8, 138.5, 196.8 ppm; Anal.
Calcd for C20H16F3NO: C, 69.96; H, 4.70; N, 4.08. Found: C, 70.15; H,
4.86; N, 3.90; ESI-MS: m/z¼344 (Mþ1)þ.
4.3.13. 1-(2-Methyl-1-phenyl-5-(5-(trifluoromethyl)phenyl)-1H-pyr-
rol-3-yl)ethanone (5m). Yellow sticky liquid (292 mg, 85%); IR
(neat): 3049, 2929, 1654, 1502, 1417, 1325, 1224, 1124, 848, 769,
4.3.7. 1-(4-(3-Chlorophenyl)-2-methyl-1-phenyl-1H-pyrrol-3-yl)
ethanone (5g). Colorless sticky liquid (272 mg, 88%); IR (neat):
698 cmꢁ1; 1H NMR (CDCl3, 500 MHz)
d 2.12 (s, 3H), 2.40 (s, 3H), 6.71
3128, 3057, 2922, 1647, 1516, 1406, 1224, 1076, 802, 767, 696 cmꢁ1
;
(s, 1H), 7.33 (d, J¼8.0 Hz, 2H), 7.45 (t, J¼7.5 Hz, 1H), 7.48e7.51 (m,
1H NMR (CDCl3, 500 MHz)
d
2.11 (s, 3H), 2.40 (s, 3H), 6.68 (s, 1H),
5H), 7.63 (d, J¼8.0 Hz, 2H) ppm; 13C NMR (CDCl3, 125 MHz)
d 12.9,
1
7.24e7.33 (m, 5H), 7.39 (s, 1H), 7.43 (t, J¼7.5 Hz, 1H), 7.49 (t,
31.2, 121.1, 122.5, 124.2 (q, JFC¼270.2 Hz), 124.8, 125.2 (q,
3JFC¼3.6 Hz),128.3, 128.8 (q, 2JFC¼32.0 Hz), 129.3, 129.4, 135.7, 138.5,
139.8197.0 ppm; Anal. Calcd for C20H16F3NO: C, 69.96; H, 4.70; N,
4.08. Found: C, 70.13; H, 4.90; N, 3.91; ESI-MS: m/z¼344 (Mþ1)þ.
J¼7.5 Hz, 2H) ppm; 13C NMR (CDCl3, 125 MHz)
d 12.9, 31.1, 120.9,
122.5, 124.8, 126.2, 126.8, 127.5, 128.3, 129.1, 129.5, 129.5, 134.1,
135.5, 137.9, 138.5, 197.1 ppm; Anal. Calcd for C19H16ClNO: C, 73.66;
H, 5.21; N, 4.52. Found: C, 73.83; H, 5.05; N, 4.71; ESI-MS: m/z¼310
(Mþ1)þ.
4.3.14. 1-(4-(Furan-2-yl)-2-methyl-1-phenyl-1H-pyrrol-3-yl)etha-
none (5n). White solid (167 mg, 63%); IR (KBr): 3120, 2982, 2926,
4.3.8. 1-(4-(4-Chlorophenyl)-2-methyl-1-phenyl-1H-pyrrol-3-yl)
1647, 1498, 1410, 1240, 1049, 952, 769 cmꢁ1 1H NMR (CDCl3,
;
ethanone (5h). White solid (266 mg, 86%); IR (KBr): 3117, 3047,
500 MHz)
7.30 (d, J¼7.5 Hz, 2H), 7.44 (t, J¼7.5 Hz, 1H), 7.47e7.50 (m, 3H) ppm;
13C NMR (CDCl3, 125 MHz)
13.0, 29.9, 107.9, 111.1, 115.3, 121.7,
121.8, 126.3, 128.3, 129.4, 135.8, 138.5, 141.7, 148.8, 196.6 ppm; Anal.
Calcd for C17H15NO2: C, 76.96; H, 5.70; N, 5.28. Found: C, 77.15; H,
5.90; N, 5.45; ESI-MS: m/z¼266 (Mþ1)þ.
d 2.22 (s, 3H), 2.40 (s, 3H), 6.43e6.45 (m, 2H), 6.85 (s, 1H),
2922, 1647, 1500, 1410, 1087, 837, 767, 700 cmꢁ1 1H NMR (CDCl3,
;
500 MHz)
d
2.09 (s, 3H), 2.39 (s, 3H), 6.66 (s, 1H), 7.30e7.36 (m, 6H),
d
7.43 (t, J¼7.5 Hz, 1H), 7.49 (t, J¼7.5 Hz, 2H) ppm; 13C NMR (CDCl3,
125 MHz)
d 12.9, 31.1, 120.7, 122.5, 125.0, 126.2, 128.2, 128.4, 129.5,
130.5, 132.7, 134.5, 135.5, 137.9, 138.6, 197.1 ppm; Anal. Calcd for
C19H16ClNO: C, 73.66; H, 5.21; N, 4.52. Found: C, 73.80; H, 5.01; N,
4.69; ESI-MS: m/z¼310 (Mþ1)þ.
4.3.15. 1-(2-Methyl-1-phenyl-4-(thiophen-2-yl)-1H-pyrrol-3-yl)
ethanone (5o). Yellow solid (197 mg, 70%); IR (KBr): 3113, 3051,
4.3.9. 1-(4-(4-Bromophenyl)-2-methyl-1-phenyl-1H-pyrrol-3-yl)
2926, 1653, 1506, 1406, 1234, 831, 771, 702 cmꢁ1 1H NMR (CDCl3,
;
ethanone (5i). White solid (307 mg, 87%); IR (KBr): 3040, 2922,
500 MHz) d 2.18 (s, 3H), 2.40 (s, 3H), 6.76 (s, 1H), 7.02 (s, 1H),
1647, 1506, 1408, 1228, 835, 765, 700 cmꢁ1
;
1H NMR (CDCl3,
7.05e7.06 (m, 1H), 7.28 (d, J¼5.0 Hz, 1H), 7.31 (d, J¼8.0 Hz, 2H), 7.43
500 MHz)
2H), 7.32 (d, J¼7.5 Hz, 2H), 7.43 (t, J¼7.5 Hz, 1H), 7.48e7.51 (m, 5H)
ppm; 13C NMR (CDCl3, 125 MHz)
12.9, 31.2, 120.7, 120.8, 122.5,
d
2.10 (s, 3H), 2.39 (s, 3H), 6.66 (s, 1H), 7.25 (d, J¼7.5 Hz,
(t, J¼7.0 Hz, 1H), 7.49 (t, J¼7.5 Hz, 2H), ppm; 13C NMR (CDCl3,
125 MHz)
d 13.0, 30.6, 117.7, 122.0, 122.9, 125.0, 126.2, 127.0, 127.2,
d
128.3, 129.4, 135.6, 136.8, 138.4, 159.5, 197.0 ppm; Anal. Calcd for
C17H15NOS: C, 72.57; H, 5.37; N, 4.98. Found: C, 72.40; H, 5.56; N,
5.17; ESI-MS: m/z¼282 (Mþ1)þ.
125.0, 126.2, 128.2, 129.5, 130.8, 131.5, 135.0, 135.5, 138.6, 197.1 ppm;
Anal. Calcd for C19H16BrNO: C, 64.42; H, 4.55; N, 3.95. Found: C,
64.60; H, 4.37; N, 4.13; ESI-MS: m/z¼355 (Mþ1)þ.
4.3.16. 1-(2-Methyl-5-(naphthalen-1-yl)-1-phenyl-1H-pyrrol-3-yl)
4.3.10. 1-(2-Methyl-4-(3-nitrophenyl)-1-phenyl-1H-pyrrol-3-yl)
ethanone (5p). White solid (260 mg, 80%); IR (KBr): 3111, 3034,
ethanone (5j). Brown sticky liquid (259 mg, 81%); IR (neat): 3080,
2914, 1653, 1504, 1398, 1238, 802, 767, 698 cmꢁ1 1H NMR (CDCl3,
;
2922, 1647, 1560, 1506, 1400, 1340, 1224, 869, 765, 698 cmꢁ1
;
1H
500 MHz)
d 1.71 (s, 3H), 2.54 (s, 3H), 6.74 (s, 1H), 7.39e7.52 (m, 9H),
NMR (CDCl3, 500 MHz)
d 2.15 (s, 3H), 2.42 (s, 3H), 6.76 (s, 1H),
7.86 (t, J¼5.0 Hz, 1H), 7.88 (d, J¼8.0 Hz, 1H), 7.95 (d, J¼8.0 Hz, 1H)