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130.4, 130.9, 132.6, 137.3, 138.5. MS (EI): 400 (M+, 3),
309 (100), 281 (3), 220 (4), 178 (5), 131 (9), 103 (24), 91
(5), 65 (2). Anal: Found: C, 83.79; H, 5.08; N, 7.04.
C28H20N2O requires C, 83.98; H, 5.03; N, 6.99.
yield 382 mg (89%), yellow crystals, mp 156–158 ꢁC, Rf
0.36 (SiO2, EtOAc–hexane; 1:4). H NMR (300 MHz,
1
CDCl3) d 3.79 (s, 3H, CH3), 4.69 (s, 2H, CH2), 6.35 (dd,
J=7.4 and 1.8 Hz, 1H, H-6), 6.80–7.24 (m, 4H, Ph),
7.24–7.34 (m, 10H, Ph), 7.64 (dd, J=1.8 and 0.9 Hz,
1H, H-8), 7.82 (dd, J=7.4 and 0.9 Hz, 1H, H-5). 13C
NMR (75 MHz, CDCl3) d 55.7, 97.5, 110.3, 114.3,
119.5, 121.5, 121.8, 121.9, 123.4, 124.3, 127.0, 128.3,
128.6, 129.0, 129.4, 129.6, 130.2, 130.4, 130.6, 130.9,
132.7, 138.8, 160.1. MS (EI): 430 (M+, 1), 414 (12), 311
(21), 310 (100), 309 (48), 281 (13), 178 (10), 170 (28), 121
(34), 115 (8), 103 (18), 99 (11). HRMS: calcd for
C29H22N2O2: 430.1681; found 430.1684. Anal: Found:
C, 80.58; H, 5.15; N, 6.02. C29H22N2O2 requires C,
80.91; H, 5.15; N, 6.51%.
1-(4-Chlorophenyl)methoxy-2,3-diphenyl-7-indolizinecar-
bonitrile (4c). The compound was prepared as descri-
bed for compound 4b above. After addition of the alkyl
halide (4-chlorobenzyl chloride) the reaction mixture
was stirred for 24 h at ambient temperature and at 50ꢁC
for 72 h. EtOAc–hexane (1:29) followed by (1:19) were
used as eluents for flash chromatography; yield 223 mg
(51%), yellow crystals, mp 163–166 ꢁC. 1H NMR
(300MHz, CDCl3) d 4.80 (s, 2H, CH2), 6.45 (dd, J=7.4
and 1.7 Hz, 1H, H-6), 7.14–7.17 (m, 2H, Ph), 7.17–7.29
(m, 10H, Ph), 7.29–7.41 (m, 2H, Ph), 7.75 (dd, J=1.7 and
0.8 Hz, 1H, H-8), 7.88 (dd, J=7.4 and 0.8 Hz, 1H, H-5).
13C NMR (75 MHz, CDCl3) d 76.5, 97.8, 110.4, 119.8,
122.0, 122.0, 122.1, 123.9, 124.5, 127.6, 128.8, 129.0, 129.1,
129.6, 130.1 (2 C), 130.4, 130.8, 132.5, 134.6, 135.7, 138.2.
MS (EI): 436/434 (M+, 0.4/2), 309 (100), 178 (4), 131
(8), 103 (22). Anal: Found: C, 77.23; H, 4.55; N, 6.14.
C28H19ClN2O requires C, 77.33; H, 4.40; N, 6.44%.
1-(3-Chlorophenyl)methoxy-2,3-diphenyl-7-indolizinecar-
bonitrile (4g). The compound was prepared as descri-
bed for compound 4b above and purified by flash
chromatography, eluting with EtOAc–hexane (1:29)
followed by (1:19); yield 396 mg (91%), yellow crystals,
mp 156–158 ꢁC. H NMR (300 MHz, CDCl3) d 4.74 (s,
1
2H, CH2), 6.39 (dd, J=7.5 and 1.8 Hz, 1H, H-6),
7.13–7.16 (m, 2H, Ph), 7.16–7.30 (m, 10H, Ph),
7.30–7.44 (m, 2H, Ph), 7.75 (d, J=1.8, 1H, H-8), 7.86
(br d, J=7.5, 1H, H-5). 13C NMR (75 MHz, CDCl3) d
76.5, 97.8, 110.5, 119.8, 122.0, 122.1, 122.1, 123.9, 124.5,
126.7, 127.6, 128.8 (2 C), 128.8, 129.1, 129.6, 130.1,
130.2, 130.4, 130.8, 132.4, 134.7, 138.2, 139.2. MS (EI):
434/434 (M+, 1/3), 309 (100), 281 (6), 178 (7), 131 (9),
103 (25). Anal: Found: C, 77.30; H, 4.54; N, 6.02.
C28H19ClN2O requires C, 77.23; H, 4.40; N, 6.44%.
1-(4-Fluorophenyl)methoxy-2,3-diphenyl-7-indolizinecar-
bonitrile (4d). The compound was prepared as descri-
bed for compound 4b above and purified by flash
chromatography, eluting with EtOAc–hexane (1:19);
yield 382 mg (91%), yellow crystals, mp 152–154 ꢁC. 1H
NMR (300 MHz, CDCl3) d 4.74 (s, 2H, CH2), 6.38 (dd,
J=7.4 and 1.8 Hz, 1H, H-6), 6.94–7.00 (m, 4H, Ph),
7.00–7.41 (m, 10H, Ph), 7.72 (1H, br d, J=1.8 Hz, 1H,
H-8), 7.83 (dd, J=7.4 and 0.8 Hz, 1H, H-5). 13C NMR
(75 MHz, CDCl3) d 76.6, 97.7, 110.4, 115.6, 115.9,
119.8, 122.0 (d, JCF=4.8 Hz, CH in Ar), 122.1, 122.2,
123.9, 124.5, 127.5, 128.7, 129.1, 129.6, 130.1, 130.4,
130.6, 130.7, 130.8, 132.6, 133.0 (d, JCF=3.3 Hz, CH in
Ar), 138.2, 163.1 (d, JCF=247 Hz). MS (EI): 418 (M+,
4), 309 (100), 178 (4), 131 (8), 109 (6), 103 (21). Anal.
Found: C, 80.17; H, 4.79; N, 6.30. C28H19FN2O
requires C, 80.37; H, 4.58; N, 6.69%.
1-(2-Methoxyphenyl)methoxy-2,3-diphenyl-7-indolizine-
carbonitrile (4h). The compound was prepared as
described for compound 4b above. After addition of the
alkyl halide (2-methoxybenzyl chloride) the reaction
mixture was stirred at 60 ꢁC for 24 h. EtOAc–hexane
(1:19) was used as eluent for flash chromatography;
yield 258 mg (60%), yellow crystals, mp 152–154 ꢁC, Rf
1
0.38 (SiO2, EtOAc–hexane; 1:4). H NMR (200 MHz,
CDCl3) d 3.89 (s, 3H, CH3), 4.76 (s, 2H, CH2), 6.42 (dd,
J=7.4 and 1.7 Hz, 1H, H-6), 6.92–7.04 (m, 2H, Ph),
7.04–7.48 (m, 12H, Ph), 7.84 (dd, J=1.7 and 0.9 Hz,
1H, H-8), 7.88 (dd, J=7.4 and 0.9 Hz, 1H, H-5). 13C
NMR (50 MHz, CDCl3) d 55.7, 72.9, 97.2, 110.3, 110.8,
120.1, 120.8, 121.9, 122.3, 122.4, 123.7, 125.1, 125.5,
127.3, 128.6, 129.0, 129.6, 130.4, 130.4 (2 C), 130.9,
130.9, 132.7, 138.8, 158.1. MS (EI): 430 (M+, 9), 309
(100), 178 (4), 131 (8), 121 (8), 103 (21), 91 (8). HRMS:
calcd for C29H22N2O2: 430.1681; found 430.1693. Anal:
Found: C, 80.57; H, 5.44; N, 6.59. C29H22N2O2 requires
C, 80.91; H, 5.15; N, 6.51%.
1-(4-Methylphenyl)methoxy-2,3-diphenyl-7-indolizinecar-
bonitrile (4e). The compound was prepared as descri-
bed for compound 4b above and purified by flash
chromatography, eluting with EtOAc–hexane (1:39) fol-
lowed by (1:29) and (1:19); yield 311 mg (75%), yellow
crystals, mp 176–178 ꢁC. 1H NMR (300 MHz, CDCl3) d
2.35 (s, 3H, CH3), 4.74 (s, 2H, CH2), 6.36 (dd, J=7.4 and
1.8 Hz, 1H, H-6), 7.14–7.24 (m, 4H, Ph), 7.24–7.42 (m,
10H, Ph), 7.65 (d, J=1.8 Hz, 1H, H-8), 7.83 (dd, J=7.4
and 0.8 Hz, 1H, H-5). 13C NMR (75 MHz, CDCl3) d
21.7, 97.5, 110.3, 119.9, 121.9, 122.1, 122.3, 123.8, 124.8,
127.5, 128.7, 129.0, 130.4, 130.9, 132.7, 134.3, 138.5,
138.6. MS (EI): 414 (M+, 4), 309 (100), 279 (4), 178 (6),
131 (10), 105 (12), 103 (30). Anal: Found: C, 84.15; H,
5.38; N, 6.38. C29H22N2O requires C, 84.03; H, 5.35; N,
6.76%.
1-Benzyloxymethoxy-2,3-diphenyl-7-indolizinecarboni-
trile (4i). The compound was prepared as described for
compound 4b above and purified by flash chromato-
graphy, eluting with EtOAc–hexane (1:19); yield 333 mg
(77%), yellow crystals, mp 132–134 ꢁC. 1H NMR
(300 MHz, CDCl3) d 4.65 (s, 2H, CH2), 5.02 (s, 2H,
CH2), 6.39 (dd, J=7.5 and 1.7 Hz, 1H, H-6), 7.17–7.32
(m, 10H, Ph), 7.38–7.40 (m, 5H, Ph), 7.86 (dd, J=7.5
and 0.9 Hz, 1H, H-5), 7.88 (dd, J=1.7 and 0.9 Hz, 1H,
1-(4-Methoxyphenyl)methoxy-2,3-diphenyl-7-indolizine-
carbonitrile (4f). The compound was prepared as
described for compound 4b above and purified by flash
chromatography, eluting with EtOAc–hexane (1:19),