1844
C.-P. Chuang, Y.-L. Wu / Tetrahedron 60 (2004) 1841–1847
(
1
q), 13.9 (q), 14.2 (q), 60.2 (t), 60.7 (t), 112.4 (s), 116.1 (s),
27.8 (d), 127.9 (d), 129.4 (d), 129.7 (d), 130.1 (s), 130.3
C H ClNO : C, 69.20; H, 5.28; N, 3.67. Found: C, 69.20;
22 20 3
H, 5.30; N, 3.62.
(
(
d), 134.4 (s), 134.5 (s), 135.5 (s), 136.0 (s), 164.7 (s), 165.8
s). Anal. calcd for C H ClNO : C, 67.07; H, 5.38; N,3.40.
3.4.6. 1-(p-Chlorophenyl)-3-ethoxycarbonyl-5-ethyl-2-
phenyl-4-propionylpyrrole 3f. Colorless needles; mp
2
3
22
4
Found: C, 67.04; H, 5.36; N, 3.38.
123–124 8C; IR(CHCl3) 2985, 1700, 1495, 1420,
1170 cm
2
1
1
3.4.2. 1-(p-Chlorophenyl)-3-ethoxycarbonyl-2-ethyl-4-
methoxycarbonyl-5-phenylpyrrole 3b. Colorless crystals;
;
H NMR (400 MHz, CDCl ) d 0.97 (t,
3
J¼7.4 Hz, 3H, CH ), 1.05 (t, J¼7.1 Hz, 3H, CH ), 1.20 (t,
3
3
mp 121–122 8C; IR(CHCl ) 2990, 1710, 1495, 1440,
3
J¼7.3 Hz, 3H, CH ), 2.59 (q, J¼7.4 Hz, 2H, CH ), 2.84 (q,
2 2
3
2
1
1
1
295 cm2
;
H NMR (400 MHz, CDCl ) d 1.02 (t,
3
J¼7.3 Hz, 2H, CH ), 4.10 (q, J¼7.1 Hz, 2H, OCH ), 7.02
J¼7.4 Hz, 3H, CH ), 1.15 (t, J¼7.1 Hz, 3H, CH ), 2.74
(d, J¼8.5 Hz, 2H, ArH), 7.09–7.13 (m, 2H, ArH), 7.15–
3
3
1
3
(
q, J¼7.4 Hz, 2H, CH ), 3.85 (s, 3H, OCH ), 4.17 (q,
7.22 (m, 3H, ArH), 7.28 (d, J¼8.5 Hz (2H, ArH); C NMR
2
3
J¼7.1 Hz, 2H, OCH ), 7.03 (d, J¼8.6 Hz, 2H, ArH), 7.09–
(100.6 MHz, CDCl ) d 8.6 (q), 13.8 (q), 14.6 (q), 18.8 (t),
3
2
7
.14 (m, 2H, ArH), 7.15–7.21 (m, 3H, ArH), 7.30 (d,
36.5 (t), 60.3 (t), 113.7 (s), 112.6 (s), 127.5 (d), 128.0 (d),
129.2 (d), 130.0 (d), 130.7 (s), 130.9 (d), 134.6 (s), 135.4 (s),
137.1 (s), 138.8 (s), 165.1 (s), 201.8 (s). Anal. calcd for
C H ClNO : C, 70.32; H, 5.90; N, 3.42. Found: C, 70.27;
1
3
J¼8.6 Hz, 2H, ArH); C NMR (100.6 MHz, CDCl ) d 14.0
3
(
1
q), 14.3 (q), 19.0 (t), 51.3 (q), 60.7 (t), 111.4 (s), 116.1 (s),
27.8 (d), 127.9 (d), 129.3 (d), 129.9 (d), 130.1 (s), 130.4
2
4
24
3
(
(
d), 134.6 (s), 134.7 (s), 135.4 (s), 142.0 (s), 165.0 (s), 165.8
s). Anal. calcd for C H ClNO : C, 67.07; H, 5.38; N,
H, 5.90; N, 3.36.
2
3
22
4
3
.40. Found: C, 67.18; H, 5.46; N, 3.35.
3.4.7. 1-(p-Bromophenyl)-3,4-diethoxycarbonyl-2-
methyl-5-phenylpyrrole 3g. Colorless crystals; mp 109–
21 1
110 8C; IR(CHCl ) 2990, 1705, 1495, 1425, 1280 cm ; H
3
.4.3. 1-(p-Chlorophenyl)-3,4-diethoxycarbonyl-2-phe-
nyl-5-propylpyrrole 3c. Colorless crystals; mp 92–93 8C;
3
NMR (400 MHz, CDCl ) d 1.16 (t, J¼7.1 Hz, 3H, CH ),
3
3
2
1 1
IR(CHCl ) 2975, 1705, 1495, 1435, 1280, 1195 cm ; H
3
1.35 (t, J¼7.1 Hz, 3H, CH ), 2.31 (s, 3H, CH ), 4.17 (q,
3
3
NMR (400 MHz, CDCl ) d 0.80 (t, J¼7.6 Hz, 3H, CH ),
J¼7.1 Hz, 2H, OCH ), 4.32 (q, J¼7.1 Hz, 2H, OCH ), 6.92
3
3
2
2
1
1
4
.14 (t, J¼7.1 Hz, 3H, CH ), 1.35 (t, J¼7.1 Hz, 3H, CH ),
(d, J¼8.5 Hz, 2H, ArH) (7.08–7.23 (m, 5H, ArH), 7.45 (d,
3
3
1
3
.43 (sextet, J¼7.6 Hz, 2H, CH ), 2.66–2.72 (m, 2H, CH ),
J¼8.5 Hz( 2H, ArH); C NMR (100.6 MHz, CDCl ) d 12.2
2
2
3
.17 (q, J¼7.1 Hz, 2H, OCH ), 4.32 (q, J¼7.1 Hz, 2H,
(q), 14.0 (q), 14.3 (q), 60.2 (t), 60.7 (t), 112.4 (s), 116.2 (s),
122.5 (s), 127.8 (d), 128.0 (d), 130.0 (d), 130.1 (s), 130.4
(d), 132.4 (d), 134.5 (s), 135.97 (s), 136.00 (s), 164.7 (s),
165.8 (s). Anal. calcd for C H BrNO : C, 60.54; H, 4.86;
2
OCH ), 7.01 (d, J¼8.6 Hz, 2H, ArH), 7.09–7.13 (m, 2H,
2
ArH), 7.15–7.20 (m, 3H, ArH), 7.29 (d, J¼8.6 Hz, 2H,
1
3
ArH); C NMR (100.6 MHz, CDCl ) d 13.9 (q), 14.0 (q),
3
23 22
4
1
(
1
4.2 (q), 23.2 (t), 27.5 (t), 60.1 (t), 60.7 (t), 112.1 (s), 116.3
s), 127.7 (d), 127.9 (d), 129.2 (d), 130.0 (d), 130.1 (s),
30.4 (d), 134.5 (s), 135.5 (s), 140.5 (s), 164.5 (s), 165.9 (s).
Anal. calcd for C H ClNO : C, 68.25; H, 5.96; N, 3.18.
N, 3.07. Found: C, 60.62; H, 4.96; N, 3.08.
3.4.8. 1-(p-Bromophenyl)-3-ethoxycarbonyl-5-ethyl-2-
phenyl-4-propionylpyrrole 3h. Colorless needles; mp
131–132 8C; IR(CHCl ) 2985, 1695, 1490, 1420, 1170,
2
5
26
4
Found: C, 68.24; H, 6.02; N, 3.20.
3
1
1
1
125 cm2
;
H NMR (400 MHz, CDCl ) d 0.97 (t,
3
3.4.4. 1-(p-Chlorophenyl)-3,4-diethoxycarbonyl-2-iso-
propyl-5-phenylpyrrole 3d. Colorless needles; mp 154–
J¼7.4 Hz, 3H, CH ), 1.05 (t, J¼7.1 Hz, 3H, CH ), 1.20 (t,
3
3
J¼7.3 Hz, 3H, CH ), 2.59 (q, J¼7.4 Hz, 2H, CH ), 2.84 (q,
3 2
2
1 1
1
55 8C; IR(CHCl ) 2985, 1715, 1495, 1270, 1190 cm ; H
3
J¼7.3 Hz, 2H, CH ), 4.10 (q, J¼7.1 Hz, 2H, OCH ), 6.96
2
2
NMR (400 MHz, CDCl ) d 1.10 (t, J¼7.2 Hz, 3H, CH ),
(d, J¼8.6 Hz, 2H, ArH), 7.09–7.13 (m, 2H, ArH), 7.16–
3
3
1
3
1
2
.25 (d, J¼7.1 Hz, 6H, CH ), 1.38 (t, J¼7.1 Hz, 3H, CH ),
7.23 (m, 3H, ArH), 7.43 (d, J¼8.6 Hz, 2H, ArH); C NMR
3
3
.87 (septet, J¼7.1 Hz, 1H, CH), 4.11 (q, J¼7.2 Hz, 2H,
(100.6 MHz, CDCl ) d 8.6 (q), 13.8 (q), 14.7 (q), 18.8 (t),
3
OCH ), 4.36 (q, J¼7.1 Hz, 2H, OCH ), 7.00 (d, J¼8.6 Hz,
36.5 (t), 60.4 (t), 113.7 (s), 122.57 (s), 122.63 (s), 127.6 (d),
128.1 (d), 130.2 (d), 130.6 (s), 130.8 (d), 132.2 (d), 135.9
(s), 137.1 (s), 138.8 (s), 165.1 (s), 201.9 (s). Anal. calcd for
C H BrNO : C, 63.44; H, 5.32; N, 3.08. Found: C, 63.45;
2
2
2
H, ArH), 7.09–7.13 (m, 2H, ArH), 7.14–7.21 (m, 3H,
1
3
ArH), 7.27 (d, J¼8.6 Hz, 2H, ArH); C NMR (100.6 MHz,
CDCl ) d 13.9 (q), 14.2 (q), 21.5 (q), 26.6 (d), 60.3 (t), 60.8
3
24 24
3
(
(
t), 113.1 (s), 114.8 (s), 127.5 (d), 128.0 (d), 129.2 (d), 130.3
d), 130.5 (s), 130.8 (d), 134.6 (s), 135.78 (s), 135.81 (s),
H, 5.37; N, 3.12.
1
C, 68.25; H, 5.96; N, 3.18. Found: C, 68.27; H, 6.01; N, 3.21.
41.9 (s), 164.8 (s), 166.2 (s). Anal. calcd for C H ClNO :
3.4.9. 3,4-Diethoxycarbonyl-1-(p-ethoxycarbonylphe-
nyl)-2-methyl-5-phenylpyrrole 3i. Colorless crystals; mp
2
5
26
4
117–118 8C; IR(CHCl3) 2990, 1715, 1485, 1270,
1190 cm
2
1
1
3.4.5. 3-Acetyl-1-(p-chlorophenyl)-4-ethoxycarbonyl-2-
methyl-5-phenylpyrrole 3e. Colorless crystals; mp 127–
;
H NMR (400 MHz, CDCl ) d 1.16 (t,
3
J¼7.1 Hz, 3H, CH ), 1.35 (t, J¼7.1 Hz, 3H, CH ), 1.37 (t,
3
3
2
1 1
1
28 8C; IR(CHCl ) 3010, 1705, 1660, 1495, 1415 cm ; H
3
J¼7.1 Hz, 3H, CH ), 2.23 (s, 3H, CH ), 4.18 (q, J¼7.1 Hz,
2 2
3
3
NMR (400 MHz, CDCl ) d 1.08 (t, J¼7.1 Hz, 3H, CH ),
2H, OCH ), 4.33 (q, J¼7.1 Hz, 2H, OCH ), 4.36 (q,
3
3
2
.21 (s, 3H, CH ), 2.51 (s, 3H, CH ), 4.13 (q, J¼7.1 Hz, 2H,
J¼7.1 Hz, 2H, OCH ), 7.09–7.20 (m, 7H, ArH), 8.01 (d,
3
3
2
1
3
OCH ), 6.98 (q, J¼8.6 Hz, 2H, ArH), 7.10–7.15 (m, 2H,
J¼8.5 Hz (2H, ArH); C NMR (100.6 MHz, CDCl ) d 12.2
2
3
ArH), 7.16–7.25 (m, 3H, ArH), 7.29 (d, J¼8.6 Hz, 2H,
(q), 14.0 (q), 14.2 (q), 14.3 (q), 60.2 (t), 60.7 (t), 61.3 (t),
112.7 (s), 116.4 (s), 127.8 (d), 128.0 (d), 128.5 (d), 130.0 (s),
130.36 (d), 130.41 (d), 134.4 (s), 135.9 (s), 140.9 (s), 164.7
(s), 165.5 (s), 165.7 (s). Anal. calcd for C H NO : C,
1
3
ArH); C NMR (100.6 MHz, CDCl ) d 12.4 (q), 13.8 (q),
3
3
1
1
1.0 (q), 60.6 (t), 114.4 (s), 123.1 (s), 127.6 (d), 128.1 (d),
29.4 (d), 129.7 (d), 130.5 (s), 130.8 (d), 134.2 (s), 134.6 (s),
35.3 (s), 136.9 (s), 165.2 (s), 197.7 (s). Anal. calcd for
2
6
27
6
69.47; H, 6.05; N, 3.12. Found: C, 69.45; H, 6.05; N, 3.04.