6
14
M. Ghandi, A. Taheri, and A. Abbasi
Vol 47
ꢁ
1
1
13
8.81 (s, 1H); C NMR: 39.9, 51.2, 52.9, 56.3, 56.5, 58.3,
76.1, 111.7, 111.8, 112.3, 114.6, 121.4, 124.3, 127.0, 129.4,
(
KBr): 2250 cm ; PH NMR: 2.39 (s, 3H), 3.20 (t, J ¼ 10.2,
1
6
3
1
[
1
H), 3.85 (dd, J ¼ 10.2, 6.6, 1H), 4.14 (m, 2H), 7.44–7.57 (m,
13
þ
H), 8.00 (bd, 1H), 8.74 (bd, 1H), 8.83 (s, 1H); C NMR:
9.9, 50.9, 52.8, 58.4, 76.4, 112.0, 114.6, 124.3, 128.8, 129.4,
136.3, 149.8, 150.3, 150.3, 151.8; MS: m/z ¼ 348 [M ] Anal.
Calcd. For C H N O : C, 68.93; H, 5.79; N, 16.08%. Found:
C, 68.35; H, 5.29; N, 15.83%.
20 20 4 2
29.6, 129.7, 135.0, 136.4, 150.4, 151.9; MS: m/z ¼ 288
þ
M ]; Anal. Calcd. For C18H
9.43%. Found: C, 74.56; H, 5.23; N, 19.72%.
16
N
4
: C, 74.97; H, 5.59; N,
N-methyl-4-(3,4,5-methoxyphenyl)-2-(pyridine-3-yl)pyrroli-
dine-3,3-dicarbonitrile (3h). White crystals; Yield: 64%; IR
ꢁ
1 1
N-methyl-4-(3-methoxyphenyl)-2-(pyridine-3-yl)pyrrolidine-
,3-dicarbonitrile (3c). White crystals; Yield: 75%; IR (KBr):
(KBr): 2245 cm ; PH NMR (syn/anti): 2.38 (s, 3H)/2.39 (s,
3H), 3.18 (t, J ¼ 10.3, 1H)/3.03 (t, J ¼ 10.3, 1H), 3.80 (dd, J
¼ 10.3, 7.0, 1H)/3.70 (dd, J ¼ 10.3, 7.0, 1H), 3.91 (s, 9H)/
3.89 (s, 9H), 4.07 (dd, J ¼ 10.3, 7.0, 1H)/4.04 (dd, J ¼ 10.3,
7.0, 1H), 4.13 (s, 1H)/4.05 (s, 1H), 6.75 (s, 2H)/6.62 (s, 2H),
7.46 (bd, 1H)/7.43 (bd, 1H), 7.99 (bd, 1H)/7.91 (bd, 1H), 8.73
3
2
3
1
ꢁ
1
1
; PH NMR (syn/anti): 2.37 (s, 3H)/2.38 (s, 3H),
248 cm
.17 (t, J ¼ 10.2, 1H)/3.05 (t, J ¼ 10.2, 1H), 3.84 (dd, J ¼
0.2, 7.0, 1H)/3.73 (dd, J ¼ 10.2, 7.0, 1H), 3.86 (s, 3H)/3.85,
s, 3H), 4.12 (dd, J ¼ 10.2, 7.0, 1H)/4.10 (dd, J ¼ 10.2, 7.0,
1
3
1
(
7
H), 4.14 (s, 1H)/4.04 (s, 1H), 6.93–6.96 (m, 2H)/7.00–7.03
m, 2H), 7.13 (bd, 1H)/7.01 (bd, 1H), 7.36–7.39 (m, 2H)/7.41–
.45 (m, 2H), 7.99 (bd, 1H)/7.92 (bd, 1H), 8.73 (bd, 1H)/8.72
(bd, 1H)/8.72 (bd, 1H), 8.82 (s, 1H)/8.79 (s, 1H); C NMR
(syn and anti mixture): 39.9, 40.0, 49.3, 51.0, 53.3, 54.5, 56.7,
56.8, 58.3, 60.1, 61.3, 61.3, 76.1, 106.0, 106.3, 112.2, 114.1,
1
3
þ
(bd, 1H), 8.82 (s, 1H)/8.79 (s, 1H); C NMR (syn and anti
mixture): 39.9, 49.4, 50.8, 52.7, 53.9, 55.8, 58.3, 60.1, 67.3,
114.6, 114.8, 124.3, 124.3; MS: m/z ¼ 378 [M ]; Anal. Calcd.
For C21H N O : C, 66.63; H, 5.86; N, 14.80%. Found: C,
22 4 3
7
1
1
6.9, 112.1, 113.8, 114.6, 114.6, 114.8, 114.9, 115.0, 115.2,
21.0, 121.1, 124.3, 124.3, 129.4, 130.6, 130.7, 130.8, 136.0,
36.4, 136.4, 136.5, 150.3, 150.4, 151.8, 151.9, 160.4, 160.49;
66.76; H, 6.12; N, 14.73%.
N-methyl-4-(4-chlorophenyl)-2-(pyridine-3-yl)pyrrolidine-
3,3-dicarbonitrile (3i). White crystals; Yield: 77%; mp 147–
148 C; IR (KBr): 2250 cm ; PH NMR: 2.38 (s, 3H), 3.19 (t,
J ¼ 10.2, 1H), 3.77 (dd, J ¼ 10.2, 6.3, 1H), 4.11 (m, 2H),
7.37–7.50 (m, 5H), 7.98 (bd, 1H), 8.74 (bd, 1H), 8.82 (s, 1H);
þ
ꢂ
ꢁ1
1
MS: m/z ¼ 318 [M ]; Anal. Calcd. For C19 N
H, 5.70; N, 17.60%. Found: C, 71.15; H, 6.10; N, 17.14%.
H
18
4
O: C, 71.66;
N-methyl-4-biphenyl-2-(pyridine-3-yl) pyrrolidine-3,3-dicar-
ꢂ
1 1
1
3
bonitrile (3d). White crystals; Yield: 77%; mp 152–153 C; IR
ꢁ
C NMR: 39.8, 50.8, 52.2, 58.5, 76.3, 112.0, 114.4, 124.3,
29.2, 129.9, 129.9, 130.2, 130.3, 133.6, 135.8, 136.3, 150.4,
1
1
6
1
(
KBr): 2246 cm ; PH NMR: 2.42 (s, 3H), 3.23 (t, J ¼ 10.2,
þ
52.0; MS: m/z ¼ 322 [M ]; Anal. Calcd. For C18
15 4
H N Cl: C,
1
1
2
3
1
1
H), 3.88 (dd, J ¼ 10.2, 6.6, 1H), 4.17 (s, 1H), 4.19 (dd, J ¼
6.96; H, 4.68; N, 17.36%. Found: C, 66.85; H, 4.94; N,
7.23%.
0.2, 6.6, 1H), 7.39–7.53 (m, 4H), 7.64 (bd, 4H), 7.71 (bd,
13
H), 8.03 (bd, 2H), 8.76 (bd, 1H), 8.82 (s, 1H); C NMR:
9.9, 50.9, 52.6, 58.4, 76.3, 112.1, 114.6, 124.3, 127.6, 128.2,
28.3, 129.3, 129.3, 129.4, 129.5, 133.8, 136.4, 136.4, 140.6,
42.6, 150.4, 152.0; MS: m/z ¼ 364 [M ]; Anal. Calcd. For
N-methyl-4-(4-methylphenyl)-2-(pyridine-3-yl)pyrrolidine-
,3-dicarbonitrile (3j). White crystals; Yield: 75%; mp 146–
3
147 C; IR (KBr): 2250 cm ; PH NMR: 2.38 (s, 3H), 2.40
ꢂ
ꢁ1
1
þ
(
4
1
s, 3H), 3.18 (t, J ¼ 10.2, 1H), 3.83 (dd, J ¼ 10.2, 6.7, 1H),
24 20 4
C H N : C, 79.12; H, 5.49; N, 15.38%. Found: C, 78.69; H,
.11 (dd, J ¼ 10.2, 6.7, 1H), 4.13 (s, 1H), 7.28 (d, J ¼ 8.0,
H), 7.43 (m, 1H), 7.45 (d, J ¼ 8.0, 1H), 8.00 (bd, 1H), 8.73
5
.51; N, 15.27%.
N-methyl-4-(4-bromophenyl)-2-(pyridine-3-yl)pyrrolidine-
,3-dicarbonitrile (3e). White crystals; Yield: 73%; mp 154–
13
(
76.2, 112.2, 114.7, 124.3, 128.7, 128.9, 129.6, 130.3, 131.9,
1
bd, 1H), 8.83 (s, 1H); C NMR: 21.6, 39.9, 51.9, 52.6, 58.3,
3
1
ꢂ
ꢁ1
1
55 C; IR (KBr): 2250 cm ; PH NMR: 2.37 (s, 3H), 3.19 (t,
þ
36.4, 139.6, 150.4, 151.9; MS: m/z ¼ 302 [M ]; Anal. Calcd.
J ¼ 10.2, 1H), 3.77 (dd, J ¼ 10.2, 6.3, 1H), 4.09 (dd, J ¼
18 4
For C19H N : C, 75.46; H, 6.00; N, 18.53%. Found: C, 74.96;
1
7
5
1
3
0.2, 6.3, 1H), 4.12 (s, 1H), 7.42–7.46 (m, 3H), 7.60 (bd, 2H),
.98 (bd, 1H), 8.74 (bd, 1H), 8.80 (s, 1H); C NMR: 39.8,
0.7, 52.2, 58.4, 76.3, 112.0, 114.4, 124.0, 124.3, 129.2, 130.5,
1
3
H, 6.38; N, 18.26%.
Spiro[9,4]-1-N-methyl-2(pyridine-3-yl)pyrrolidine-3,3-dicar-
ꢂ
bonitrile (3k). White crystals; Yield: 75%; mp 222–223 C; IR
1 1
30.6, 132.9, 134.2, 136.3, 150.4, 151.9, 152.0; MS: m/z ¼
ꢁ
þ
(KBr): 2243 cm ; PH NMR: 2.46 (s, 3H), 3.28 (d, J ¼ 10.3,
67 [M ]; Anal. Calcd. For C18
H
15
N
4
Br: C, 58.85; H, 4.11;
1
H), 3.78 (d, J ¼ 10.3, 1H), 4.44 (s, 1H), 7.45–7.56 (m, 5H), 7.71
N, 15.25%. Found: C, 58.36; H, 3.89; N, 15.05%.
N-methyl-4-(4-methoxyphenyl)-2-(pyridine-3-yl)pyrrolidine-
(
(
(
d, J ¼ 7.5, 1H), 7.76 (d, J ¼ 7.3, 1H), 7.80 (d, J ¼ 7.4, 1H), 8.01
d, J ¼ 7.4, 1H), 8.01 (d, J ¼ 7.8, 1H), 8.77 (d, J ¼ 3.6, 1H), 8.96
3
1
,3-dicarbonitrile (3f). White crystals; Yield: 64%; mp 138–
ꢁ1
13
1
39 C; IR (KBr): 2248 cm ; PH NMR: 2.37 (s, 3H), 3.17 (t,
s, 1H); C NMR: 39.9, 53.8, 60.8, 65.9, 77.4, 113.1, 113.3,
ꢂ
1
1
3
1
20.7, 121.1, 124.4, 125.9, 126.6, 128.4, 128.6, 129.6, 130.2,
30.5, 136.8, 140.6, 141.2, 144.6, 145.4, 150.6, 152.0; MS: m/z ¼
J ¼ 10.2, 1H), 3.78 (dd, J ¼ 10.2, 6.7, 1H), 3.84 (s, 3H), 4.10
(
dd, J ¼ 10.2, 6.7, 1H), 4.12 (s, 1H), 6.98 (d, J ¼ 8.6, 2H),
þ
62 [M ]; Anal. Calcd. For C24
H
18
N
4
: C, 79.56; H, 4.97; N,
7
1
1
1
.42 (m, 1H), 7.47 (d, J ¼ 8.6, 2H), 7.99 (bd, 1H), 8.72 (bd,
5.47%. Found: C, 79.34; H, 4.63; N, 15.48%.
1
3
H), 8.82 (s, 1H); C NMR: 39.9, 51.2, 52.4, 55.8, 58.4, 76.2,
12.2, 114.7, 115.0, 124.3, 126.8, 129.6, 130.0, 136.3, 150.4,
þ
Acknowledgment. The authors acknowledge the University of
Tehran for financial support of this research.
51.9, 160.7; MS: m/z ¼ 318 [M ]; Anal. Calcd. For
19 18 4
C H N O: C, 71.66; H, 5.70; N, 17.60%. Found: C, 71.33;
H, 5.42; N, 17.47%.
N-methyl-4-(3,4-methoxyphenyl)-2-(pyridine-3-yl)pyrrolidine-
REFERENCES AND NOTES
3
1
,3-dicarbonitrile (3g). White crystals; Yield: 70%; mp 111–
ꢁ1
[
1] (a) Pailer, M. In Tobacco Alkaloids and Related Com-
ꢂ
1
12 C; IR (KBr): 2252 cm ; PH NMR: 2.37 (s, 3H), 3.18 (t,
pounds; von Euler, U. S., Ed.; Pergamon: New York, 1965; p 15; (b)
Gorrod, J. W.; Jacob, P. In Analytical Determination of Nicotine and
Related Compounds and Their Metabolites; Elsevier: New York, 1999;
pp 1–9.
J ¼ 10.2, 1H), 3.80 (dd, J ¼ 10.2, 7.0, 1H), 3.91 (s, 3H), 3.95
s, 3H), 4.08 (dd, J ¼ 10.2, 7.0, 1H), 4.12 (s, 1H), 6.92 (d, J
8.2, 2H), 7.06 (s, 1H), 7.10 (d, J ¼ 8.2, 2H), 8.72 (bd, 1H),
(
¼
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet