10.1002/adsc.201700313
Advanced Synthesis & Catalysis
9H); 13C NMR (75 MHz, CDCl3):163.7 (CO), 159.4 1H), 4.42-4.29 (m, 2H), 4.15-3.99 (m, 2H), 1.58 (s, 9H)
(CO), 142.7 (C), 131.9 (CH), 126.2 (C), 122.4 (CH), 121.7 1.39 (t, J = 7.0 Hz, 3H), 1.16 (t, J = 7.3 Hz, 3H); 13C NMR
(C), 101.4 (CH), 81.3 (C), 80.4 (C), 55.1 (CH2), 28.4 (CH3), (75 MHz, CDCl3): 169.3 (CO), 164.8 (CO), 152.4 (C),
28.2 (CH3); HRMS (ESI) calcd. for C17H23NNaO4 136.7 (C), 134.1 (CH), 130.3 (CH), 128.6 (CH), 124.8 (C),
[M+Na]+: 328.1525, found: 328.1522.
124.1 (CH), 123.8 (CH), 82.5 (C), 61.5 (CH2), 61.1 (CH2),
53.3 (CH), 28.2 (CH3), 14.2 (CH3), 13.9 (CH3); IR: νmax
=
Diethyl 4H-pyrrolo[3,2,1-ij]quinoline-4,5-dicarboxylate 2980, 2936, 2908, 1744, 1710, 1368, 1290, 1247, 1230,
(3c) (43 mg, 96 % yield; Microwave: 44 mg, 99% yield). 1202, 1156, 1128, 1025, 946, 856, 765 cm-1; HRMS (ESI)
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Yellow solid; mp 93–95 °C; Rf 0.76 (30% EtOAc/PE); H calcd. for C20H25NNaO6 [M+Na]+: 398.1580, found:
NMR (300 MHz, CDCl3): 7.80 (d, J = 1.1 Hz, 1H), 398.1573.
7.48 (dd, J = 7.7, 1.0 Hz, 1H), 7.22 (d, J = 3.4 Hz, 1H),
7.07-6.91 (m, 2H), 6.47 (d, J = 3.0 Hz, 1H), 6.04 (s, 1H), Diethyl
1-tosyl-1,2-dihydrobenzo[4,5]thieno[3,2-
4.30-4.20 (m, 2H), 4.19-4.01 (m, 2H), 1.29 (t, J = 7.2 Hz, b]pyridine-2,3-dicarboxylate (3g) (44 mg, 60% yield;
3H), 1.17 (t, J = 7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): Microwave: 44 mg, 60% yield). Yellow solid; mp 173–
1
168.3 (CO), 165.3 (CO), 134.6 (CH), 133.4 (C), 126.2 176 °C; Rf 0.67 (30% EtOAc/PE); H NMR (300 MHz,
(CH), 125.1 (C), 124.3 (CH), 122.1 (C), 121.5 (CH), 120.9 CDCl3): 8.32 (dd, J = 8.5, 1.0 Hz, 1H), 7.69 (dd, J =
(CH), 116.0 (C), 103.7 (CH), 62.1 (CH2), 61.1 (CH2), 58.4 7.9, 0.8 Hz, 1H), 7.48-7.31 (m, 2H), 7.19-7.13 (m, 2H),
(CH), 14.3 (CH3), 14.0 (CH3); IR: νmax = 2982, 2931, 1743, 7.02-6.89 (m, 3H), 6.05 (s, 1H), 4.26-4.09 (m, 2H), 4.03-
1699, 1598, 1370, 1288, 1248, 1212, 1058, 1024, 1151, 3.85 (m, 2H), 2.27 (s, 3H), 1.25 (t, J = 7.2 Hz, 3H), 0.99 (t,
794 cm-1; HRMS (ESI) calcd. for C17H18NO4 [M+H]+: J = 7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3): 167.8
300.1236, found: 300.1223.
(CO), 163.7 (CO), 144.5 (C), 138.9 (C), 134.7 (C), 134.1
(C), 131.3 (C), 129.0 (CH), 128.1 (C), 127.2 (CH), 127.0
Diethyl
1-bromo-4H-pyrrolo[3,2,1-ij]quinoline-4,5- (CH), 126.5 (CH), 125.6 (CH), 125.3 (CH), 123.2 (C),
dicarboxylate (3d) (53 mg, 94 % yield; Microwave: 56 mg, 122.4 (CH), 62.1 (CH2), 61.1 (CH2), 57.4 (CH), 21.5 (CH3),
99% yield). Green solid; mp 67–70 °C; Rf 0.67 (30% 14.3 (CH3), 13.8 (CH3); IR: νmax = 3068, 2982, 2940, 1739,
1
EtOAc/PE); H NMR (300 MHz, CDCl3): 7.77 (d, J = 1703, 1608, 1500, 1365, 1292, 1258, 1236, 1185, 1170,
1.1 Hz, 1H), 7.40 (dd, J = 7.2, 1.5 Hz, 1H), 7.24 (s, 1H), 1145, 1089, 1020, 769, 731 cm-1; HRMS (ESI) calcd. for
7.10-6.98 (m, 2H), 5.96 (bs, 1H), 4.24 (qd, J = 7.2, 1.1 Hz, C24H24NO6S2 [M+H]+: 486.1045, found: 486.1037.
2H), 4.19-4.03 (m, 2H), 1.29 (t, J = 7.1 Hz, 3H), 1.19 (t, J
= 7.1 Hz, 3H); 13C NMR (75 MHz, CDCl3): 167.8 (CO), Diethyl
1-tosyl-1,2,5,6-tetrahydropyridine-2,3-
165.0 (CO), 133.8 (CH), 132.8 (C), 125.1 (CH), 124.5 (C), dicarboxylate (5a) (45 mg, 79 % yield; Microwave: 46 mg,
122.6 (CH), 122.4 (CH), 121.9 (C), 121.6 (CH), 116.2 (C), 81% yield). Colorless oil; Rf 0.5 (30% EtOAc/PE); 1H
92.7 (C), 62.3(CH2), 61.4 (CH2), 58.2 (CH), 14.2 (CH3), NMR (300 MHz, CDCl3): 7.73 (d, J = 8.5 Hz, 2H),
14.0 (CH3); IR: νmax = 2982, 2931, 1743, 1602, 1598, 1368, 7.28 (d, J = 8.5 Hz, 2H), 7.13-7.04 (m, 1H), 5.43 (s, 1H),
1289, 1244, 1214, 1179, 1069, 1023, 790, 742 cm-1; HRMS 4.30-4.17 (m, 2H), 4.14-3.97 (m, 2H), 3.89 (dd, J = 14.0,
(ESI) calcd. for C17H17BrNO4 [M+H]+: 378.0341, found: 7.0 Hz, 1H), 3.30-3.19 (m, 1H), 2.42 (s, 3H), 2.39-2.28 (m,
378.0342.
1H), 2.26-2.14 (m, 1H), 1.29 (t, J = 7.3 Hz, 3H), 1.19 (t, J
= 7.3 Hz, 3H); 13C NMR (75 MHz, CDCl3): 168.8 (CO),
5,6-diethyl
2-methyl
6H-indolo[3,2,1-de][1,5] 164.5 (CO), 143.6 (C), 139.3 (CH), 137.1 (C), 129.5 (2CH),
naphthyridine-2,5,6-tricarboxylate (3e) (53 mg, 86 % 127.2 (CH), 127.1 (C), 61.6 (CH2), 61.0 (CH2), 54.2 (CH),
yield; Microwave: no reaction). Yellow-orange solid; mp 38.5 (CH2), 24.5 (CH2), 21.5 (CH3), 14.1 (CH3), 13.9
167–170 °C; Rf 0.17 (30% EtOAc/PE); 1H NMR (300 MHz, (CH3); IR: νmax = 2982, 2937, 2905, 1732, 1712, 1345,
CDCl3): 8.67 (s, 1H), 8.14 (s, 1H), 8.09 (d, J = 7.9 Hz, 1263, 1160, 1102, 1047, 1025, 996, 816, 716 cm-1; HRMS
1H), 7.65 (d, J = 8.5 Hz, 1H), 7.57 (t, J = 7.6 Hz, 1H), 7.34 (ESI) calcd. for C18H24NO6S [M+H]+: 382.1324, found:
(t, J = 7.3 Hz, 1H), 6.27 (s, 1H), 4.37-4.23 (m, 2H), 4.03- 382.1319.
4.15 (m, 2H), 3.99 (s, 3H), 1.32 (t, J = 7.3 Hz, 3H), 1.08 (t,
J = 7.3 Hz, 3H); 13C NMR (75 MHz, CDCl3): 166.7 1-benzyl 2,3-diethyl 5,6-dihydropyridine-1,2,3(2H)-
(CO), 166.3 (CO), 164.5 (CO), 141.0 (C), 139.4 (C), 135.9 tricarboxylate (5b) (49 mg, 90% yield; Microwave: 50 mg,
(C), 135.6 (C), 135.2 (CH), 129.1 (CH), 128.4 (C), 125.9 92% yield). Orange oil; Rf 0.53 (30% EtOAc/PE); 1H NMR
(C), 122.8 (CH), 122.3 (C), 122.1 (CH), 119.8 (CH), 111.6 (300 MHz, CDCl3, rotamers): 7.46-7.28 (m, 5H), 7.12
(CH), 62.5 (CH2), 61.8 (CH2), 57.3 (CH), 52.8 (CH3), 14.1 (m, 1H), 5.63 (s, 0.4H), 5.52 (s, 0.6H), 5.34-5.08 (m, 2H),
(CH3), 13.9 (CH3); IR: νmax = 2982, 2949, 1740, 1707, 1635, 4.37-4.08 (m, 5H), 3.23-2.92 (m, 1H), 2.52-2.18 (m, 2H),
1435, 1373, 1269, 1248, 1223, 1192, 1165, 1116, 1020, 1.36-1.14 (m, 6H); 13C NMR (75 MHz, CDCl3, rotamers):
767, 750 cm-1; HRMS (ESI) calcd. for C22H21N2O6 165.0 (CO), 139.1 (CH), 138.4 (CH), 136.4 (C), 128.5
[M+H]+: 409.1400, found: 409.1389.
(CH), 128.4 (CH), 128.1 (CH), 128.0 (CH), 127.7 (CH),
127.5 (C), 67.6 (CH2), 67.5 (CH2), 61.6 (CH2), 60.9 (CH2),
1-tert-butyl- 2,3-diethyl
quinoline-1,2,3(2H)- 54.0 (CH), 53.8 (CH), 37.8(CH2), 37.2 (CH2), 25.2 (CH2),
tricarboxylate (3f) (41 mg, 73% yield (formation of a by- 24.9 (CH2), 14.1 (CH3), 14.0 (CH3); IR: νmax = 2982, 2937,
product (10%)); Microwave: 39 mg, 70% yield). White 2902, 1736, 1706, 1657, 1422, 1367, 1337, 1285, 1236,
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solid; mp 131–134 °C; Rf 0.76 (30% EtOAc/PE); H NMR 1210, 1192, 1108, 1051, 1024, 762, 699 cm-1; HRMS (ESI)
(300 MHz, CDCl3): 7.81 (bs, 1H), 7.57 (s, 1H), 7.39- calcd. for C19H24NO6 [M+H]+: 362.1604, found: 362.1605.
7.33 (m, 1H), 7.30-7.26 (m, 2H), 7.13-7.08 (m, 1H), 6.31 (s,
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