1
4
ACCEPTED MANUSCRIPT
Hz, 2Н, СН CH ), 7.09 (d, J=7.5 Hz, 1H), 7.21 (app. s, 6H), 7.38−7.52 (m, 2Н), 7.65 (d, J=7.5
2
3
1
3
Hz, 1H), 8.31 (s, 1H), 9.41 (d, J=7.4 Hz, 1H); C NMR (CDCl ) δ ppm: 13.5, 29.1, 29.4, 60.0,
3
1
1
13.7, 114.0, 114.5, 123.7, 124.7 (2C), 126.8, 127.1, 127.2, 127.3, 127.4, 127.8, 129.2, 130.7,
-1
31.7, 134.5, 136.7, 146.3, 146.9, 149.9, 150.7, 159.8, 161.7; IR, cm : 1663, 1719 (C=O);
UV−vis, λmax (lg ε), nm: 267 (4.90), 281 (4.93), 326 shoulder (4.48), 339 (4.40), 364 (4.33), 401
+
(
3.65); MS m/z: 505 ([M ], 100), 476 (15), 458 (21), 432 (22). Anal. calcd for C H N O : C,
2
9
23
5
4
6
8.90; H, 4.59; N, 13.85. Found: C, 68.81; H, 4.45; N, 14.09.
4
.3.6. Ethyl 1-(3-chloropyrazin-2-yl)-2-phenylpyrrolo[2,1-a]isoquinoline-3-carboxylate (17).
o
1
Yellow solid with mp 144−146 C (i-PrOH); H NMR (CDCl ) δ ppm: 0.99 (t, J=7.0 Hz, 3Н,
3
СН CH ), 4.18 (m, 2Н, СН CH ), 7.08−7.17 (m, 2Н), 7.21−7.32 (m, 6Н), 7.48 (t, J=7.4 Hz, 1Н),
2
3
2
3
1
3
7
.72 (d, J=7.8 Hz, 1H), 8.37 (s, 1H), 8.60 (d, J = 1.5 Hz, 1H), 9.48 (d, J=7.6 Hz, 1H); C NMR
(
CDCl ) δ ppm: 13.6, 60.0, 113.4, 114.0, 114.3, 123.1, 125.0, 127.0, 127.1, 127.2, 127.6, 127.7,
3
-1
1
29.0, 130.2, 130.3, 130.6, 134.4, 136.4, 142.5, 142.7, 151.2, 151.3, 161.8; IR, cm : 1694
(C=O); UV−vis, λmax (lg ε), nm: 276 (4.88), 326 (4.23), 346 (4.19), 364 (4.14); MS m/z: 427
+
(
[M ], 100), 355 (40), 346 (16), 318 (54), 292 (12), 266 (16), 159 (25). Anal. calcd for
C H ClN O : C, 70.18; H, 4.24; Cl, 8.29; N, 9.82. Found: C, 70.34; H, 4.05; Cl, 8.03; N, 10.11.
25
18
3
2
4
.3.7. Ethyl 2-phenyl-1-(3-(phenylethynyl)quinoxalin-2-yl)indolizine-3-carboxylate (18). Yellow
o
1
solid with mp 182−184 C (i-PrOH); H NMR (CDCl ) δ ppm: 0.97 (t, J=7.1 Hz, 3Н, СН CH ),
3
2
3
4
1
1
1
.14 (m, 2Н, СН CH ), 6.93 (td, J=7.0, 1.3 Hz, 1H), 7.04−7.32 (m, 11Н), 7.58 (dm, J=8.9 Hz,
2 3
13
H), 7.68−7.75 (m, 2H), 7.96−8.08 (m, 2H), 9.68 (d, J=7.2 Hz, 1H); C NMR (CDCl ) δ ppm:
3
3.7, 59.9, 88.0, 94.3, 112.0, 113.1, 113.6, 117.9, 121.8, 123.7, 126.9, 127.0 (2C), 127.9, 128.3,
28.8, 129.1, 129.3, 130.1, 130.4, 130.9, 132.2, 134.6, 136.2, 137.7, 140.4, 140.7, 151.1, 162.1;
-1
IR, cm : 1677 (C=O), 2216 (С≡С); UV−vis, λ
(lg ε), nm: 286 (4.64), 338 (4.59), 412 (3.92);
max
+
MS m/z: 493 ([M ], 100), 420 (13), 293 (33), 210 (11). Anal. calcd for C H N O : C, 80.31; H,
3
3
23
3
2
4
.70; N, 8.51. Found: C, 80.54; H, 4.55; N, 8.37.
4
.3.8. Ethyl 2-p-tolyl-1-(3-(p-tolylethynyl)quinoxalin-2-yl)indolizine-3-carboxylate (19). Yellow
o
1
solid with mp 176−177 C (i-PrOH); H NMR (CDCl ) δ ppm: 1.02 (t, J=7.1 Hz, 3Н, СН CH ),
3
2
3
2
7
.22 (s, 3H, CH ), 2.32 (s, 3H, CH ), 4.17 (m, 2Н, СН CH ), 6.87−6.94 (m, 3Н), 7.04−7.15 (m,
3 3 2 3
Н), 7.55 (dm, J=8.9 Hz, 1H), 7.68−7.74 (m, 2H), 7.98−8.08 (m, 2H), 9.65 (d, J=7.2 Hz, 1H);
1
3
C NMR (CDCl ) δ ppm: 13.8, 21.2, 21.6, 59.8, 87.6, 94.8, 112.0, 113.1, 113.5, 117.8, 118.8,
3
1
23.5, 127.7, 127.9, 128.8, 129.0, 129.1, 130.0, 130.2, 130.8, 131.5, 132.1, 136.2, 136.5, 137.9,