1
736
L. Zhang et al.
PAPER
Table 4 Physical and Spectral Data of 3-Unsubstituted Indolizines 5a−oa
o
1
5
a
Color
white
mp ( C)
IR (KBr)
H NMR (CDCl /TMS)
, J (Hz)
MS (70 eV)
m/z (%)
3
−1
(
cm )
+
83 84
3101, 1729,
8.10 (d, 1 H, J = 9.0), 7.91 (d, 1 H, J = 7.0), 7.58 (s, 1 H), 7.03 261 (M , 100), 216
(m, 1 H), 6.71 (m, 1 H), 4.36 (q, 2 H, J = 7.0), 4.34 (q, 2 H, J = (42), 188 (100), 117
1
687, 1638
7
.0), 1.37 (t, 3 H, J = 7.2), 1.36 (t, 3 H, J = 7.2)
(48) 78 (13)
52 53b
oil
2966, 2207
3114, 1694
8.00 (d, 1 H, J = 6.0), 7.61 (d, 1 H, J = 9.0), 7.22 (d, 1 H, J =
142 (M , 100), 115
+
b
c
white
3
.0), 7.05 7.00 (m, 2 H), 6.73 (m, 1H)
(22), 78 (11)
+
brown
8.14 (d, 1 H, J = 9.0), 7.93 (d, 1 H, J = 7.0), 7.20 (d, 1 H), 7.17 175 (M , 83), 144
(
d, 1 H), 6.99 (m, 1 H), 6.63 (m, 1 H), 3.87 (s, 3 H)
(100), 116 (21), 89 (75),
3 (29)
6
+
d
e
f
greenish
yellow
white
58 60
206
3124, 1635
1705, 1638
8.49 (d, 1 H, J = 9.0), 8.02 (d, 1 H, J = 7.0), 7.42 (s, 5 H), 7.21
.18 (m, 2 H), 6.64 6.42 (m, 1 H), 2.10 (s, 3 H, COCH3)
235 (M , 42), 220
(100), 191 (34)
7
+
8.24 (d, 1 H, J = 9.0), 8.17 (d, 1 H, J = 6.0), 7.73 (m, 1 H), 7.65 235 (M , 100), 206 (9)
(
s, 1 H), 7.36 7.21 (m, 4 H), 6.92 (t, 1 H, J = 6.0)
118 120c 1722, 1701
8.26 (d, 1 H, J = 8.0), 7.74 (s, 1 H), 7.67 (d, 1 H, J = 7.0), 7.58 311 (M , 38), 266 (17),
+
(
(
1
d, 1 H, J = 8.0), 7.50 (t, 1 H, J = 7.0), 7.45 (t, 1 H, J = 7.0), 6.88 238 (45), 167 (29), 128
d, 1 H, J = 7.0), 4.51 (q, 2 H, J = 7.0), 4.35 (q, 2 H, J = 7.0),
.44 (t, 3 H, J = 7.0), 1.38 (t, 3 H, J = 7.0)
(100), 77 (29)
+
g
h
i
green
green
yellow
160d
2207
1697
1640
8.80 (d, 1 H, J = 8.0), 7.77 (d, 1 H, J = 7.0), 7.86 7.20 (5 H, m), 192 (M , 100), 164 (18)
6
.96 (d, 1 H, J = 7.0)
+
97 99
116 118
9.82 (d, 1 H, J = 8.0), 9.76 (d, 1 H, J = 7.0), 7.61 7.18 (m, 5 H) 225 (M , 73), 194
(
100), 167 (14)
+
8.74 (d, 1 H, J = 8.0), 7.73 (d, 1 H, J = 7.0), 7.59 (d, 1 H, J =
285 (M , 48), 270
(100), 241 (34)
8
2
.0), 7.50 7.35 (m, 7 H), 7.25 (s, 1 H), 6.90 (d, 1 H, J = 7.0),
.26 (s, 3 H)
+
j
yellow
white
199 201
52
1739, 1609
1731, 1696
8.75 (d, 1 H, J = 8.0), 8.53 (d, 1 H, J = 8.0), 8.11 (s, 1 H), 7.84 285 (M , 100), 256
(
d, 1 H, J = 7.0), 7.66 7.27 (m, 6 H), 7.04 (d, 1 H, J = 7.0)
(21), 228 (24)
+
k
8.57 (d, 1 H, J = 9.0), 7.52 (s, 1 H), 7.03 (m, 1 H), 6.60 (d, 1 H, 275 (M , 100), 230
J = 7.0), 4.38 (q, 2 H, J = 7.0), 4.36 (q, 2 H, J = 7.0), 2.54 (s, 3 (49), 202 (78), 158 (21),
H), 1.38 (t, 6 H, J = 7.0)
130 (38), 77 (24)
+
l
white
67 68
1732, 1690,
7.89 (s, 1 H), 7.80 (d, 1 H, J = 7.0), 7.49 (s, 1 H), 6.55 (d, 1 H, 275 (M , 100), 230
J = 6.0), 4.34 (q, 2 H, J = 7.0), 4.33 (q, 2 H, J = 7.0), 2.34 (s, 3 (63), 204 (90), 178 (26),
1
644
H), 1.36 (t, 3 H, J = 7.0), 1.35 (t, 3 H, J = 7.0)
160 (26), 130 (53), 104
(
21), 77 (27)
+
m
yellow
104
1717, 1675
7.87 (s, 1 H), 7.46 (s, 1 H), 6.47 (s, 1 H), 4.39 (q, 2 H, J = 7.0), 289 (M , 100), 244
4
.36 (q, 2 H, J = 7.0), 2.52 (s, 3 H), 2.35 (s, 3 H), 1.40 (t, 3 H, (46), 216 (62), 189 (19),
J = 7.0), 1.38 (t, 3 H, J = 7.0)
172 (38), 145 (50), 128
39), 99 (23), 77 (33),
3 (93)
(
4
+
n
o
white
92−93
1721, 1692,
8.94 (s, 1 H), 8.14 (d, 1 H, J = 10.0), 7.70 (s, 1 H), 7.5 (d, 1
319 (M , 100), (34),
1681
H, J = 10.0), 4.41 (q, 2 H, J = 7.0), 4.40 (q, 2 H, J = 7.0), 3.97 246 (63), 175 (21)
s, 3 H), 1.42 (t, 3 H, J = 7.0), 1.41 (t, 3 H, J = 7.0)
(
+
colorless 174−176
1713, 1680,
611
8.24 (s, 1 H), 8.02 (d, 1 H, J = 10.0), 7.94 (d, 1 H, J = 8.0),
7.74 (d, 1 H, J = 8.0), 7.62 (1 H, t, J = 8.0), 7.46 (1 H, t, J =
311 (M , 100), 266
1
(40), 238 (79), 194
(23), 167 (40)
7
4
.0), 7.35 (d, 1 H, J = 9.0), 4.42 (4 H, m), 1.44 (t, 3 H, J =
.0), 1.42 (t, 3 H, J = 4.0)
a
Satisfactory elemental analyses obtained: C 0.28, H 0.30, N 0.29.
b
c
d
9b
o
Lit. mp 53 C.
9b
o
Lit. mp 111 112 C.
9b
o
Lit. mp 159−160 C.
Synthesis 2000, No. 12, 1733–1737 ISSN 0039-7881 © Thieme Stuttgart · New York