Molecules 2021, 26, 2066
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1-(2-(4-cyanophenyl)-2-oxoethyl)quinolin-1-ium bromide 5c
Pink powder; yield: 92%; mp 264–265 ◦C; IR (KBr),
max 3018, 2979, 2871, 2228, 1691,
1595, 1402, 1228, 1167, 1103, 991, 823 cm−1; 1H-NMR (DMSO-d6)
: 7.08 (2H, s, H-11), 8.07
ν
δ
(1H, t, J = 8.0 Hz, H-6), 8.19 (2H, d, J = 8.5 Hz, H-15, H-17), 8.23 (1H, t, J = 8.0 Hz, H-7), 8.30
(2H, d, J = 8.0 Hz, H-14, H-18), 8.34 (1H, dd, J = 8.5; 6.0 Hz, H-3), 8.53 (1H, d, J = 9.0 Hz,
H-5), 8.56 (1H, d, J = 8.0 Hz, H-8), 9.48 (1H, d, J = 8.0 Hz, H-4), 9.55 (1H, d, J = 5.5 Hz, H-2);
13C-NMR (DMSO-d6)
δ: 63.5 (C-11), 116.3 (C-16), 118.0 (CN), 119.3 (C-5), 122.2 (C-3), 129.3
(C-14, C-18), 129.4 (C-9), 130.0 (C-6), 130.6 (C-8), 133.0 (C-15, C-17), 136.0 (C-7), 136.9 (C-13),
138.7 (C-10), 148.8 (C-4), 151.0 (C-2), 190.4 (C-12); Anal. Calcd. for C18H13BrN2O2 C, 61.21;
H, 3.71; N, 7.93. Found C, 61.19; H, 4.46; N, 7.96.
3-(4-Methoxybenzoyl)-1,2,3,10b-tetrahydropyrrolo[2,1-a]isoquinoline-1,2-dicarbonitrile 7a
Yellow solid; yield: 57%; mp 200–202 ◦C; IR (KBr),
νmax 2950; 2243, 1681, 1628, 1601,
1315, 1269, 1170, 1150, 772 cm−1; 1H-NMR (DMSO-d6)
δ
: 3.79 (1H, dd, J = 9.5; 8.0 Hz, H-3),
3.85 (1H, s, OMe), 4.26 (1H, dd, J = 7.5; 2.5 Hz, H-2), 4.32 (1H, d, J = 9.5 Hz, H-10), 5.64
(1H, d, J = 7.5 Hz, H-8), 6.04 (1H, d, J = 2.5 Hz, H-1), 6.78 (1H, d, J = 7.5 Hz, H-9), 7.06–7.10
(3H, overlapped signals, H-4, H-16, H-18), 7.14–7.18 (2H, overlapped signals, H-6, H-7),
7.03 (1H, dt, J = 7.5; 1.0 Hz, H-5), 8.11 (2H, d, J = 9.0 Hz, H-15, H-19); 13C-NMR (DMSO-d6)
δ
: 29.9 (C-2), 38.8 (C-3), 55.7 (OMe), 62.7 (C-10), 71.5 (C-1), 102.1 (C-8), 114.1 (C-16, C-18),
118.2 (C-21), 119.2 (C-20), 124.5 (C-4), 126.0 (C-11), 126.1 (C-6), 126.6 (C-14), 126.7 (C-7),
129.2 (C-5), 130.3 (C-12), 131.2 (C-15, C-19), 135.2 (C-9), 163.8 (C-17), 190.7 (C-13); Anal.
Calcd. for C22H17N3O2 C, 74.35; H, 4.82; N, 11.82. Found C, 74.36; H, 4.80; N, 11.85.
3-(4-Bromobenzoyl)-1,2,3,10b-tetrahydropyrrolo[2,1-a]isoquinoline-1,2-dicarbonitrile 7b
◦
Yellow powder; yield: 80%; mp 207–209 C; IR (KBr),
ν
max 2967; 2245, 1695, 1626, 1573,
1482, 1211, 981, 740 cm−1; 1H-NMR (DMSO-d6)
δ: 4.33 (1H, dd, J = 7.5; 4.5 Hz, H-3), 4.40
(1H, dd, J = 6.0; 4.5 Hz, H-2), 5.04 (1H, d, J = 6.5 Hz, H-10), 5.38 (1H, d, J = 7.5 Hz, H-8),
6.00 (1H, d, J = 8.0 Hz, H-1), 6.46 (1H, d, J = 7.5 Hz, H-9), 7.00 (1H, d, J = 7.5 Hz, H-4), 7.00
(1H, t, J = 7.5 Hz, H-6), 7.19–7.22 (2H, overlapped signals, H-5, H-7), 7.82 (2H, d, J = 8.0 Hz,
H-16, H-18), 8.05 (2H, d, J = 8.5 Hz, H-15, H-19); 13C-NMR (DMSO-d6)
δ: 32.5 (C-2), 40.3
(C-3), 61.2 (C-10), 67.8 (C-1), 100.3 (C-8), 117.5 (C-20), 118.1 (C-21), 124.2 (C-4), 125.5 (C-11),
125.8 (C-6), 127.0 (C-7), 128.6 (C-17), 128.8 (C-5), 130.9 (C-15, C-19), 131.8 (C-12), 132.1 (C-16,
C-18), 133.3 (C-14), 134.3 (C-9), 193.0 (C-13); Anal. Calcd. for C21H14BrN3O C, 62.39; H,
3.49; N, 10.39. Found C, 62.41; H, 3.48; N, 10.42.
3-(4-cyanobenzoyl)pyrrolo[2,1-a]isoquinoline-1-carbonitrile 8c
◦
Yellow powder; yield: 65%; mp 205–206 C; IR (KBr),
ν
max 3149, 2961, 2221, 1612, 1450,
1343, 1260, 1217, 950, 803 cm−1; 1H-NMR (CDCl3)
δ: 7.39 (1H, d, J = 7.5 Hz, H-8), 7.54 (1H,
s, H-2), 7.76–7.78 (2H, overlapped signals, H-5, H-6), 7.85–7.88 (3H, overlapped signals,
H-16, H-18, H-7), 7.93 (2H, d, J = 8.5 Hz, H-15, H-19), 9.02 (1H, dd, J = 8.5; 3.5 Hz, H-4),
9.59 (1H, d, J = 7.5 Hz, H-9); 13C-NMR (CDCl3)
δ: 86.8 (C-1), 115.8 (C-17), 116.6 (C-8), 116.8
(CN), 118.1 (pCN), 123.6 (C-3), 123.9 (C-11), 124.4 (C-4), 125.2 (C-9), 127.5 (C-7), 129.3 (C-5),
129.5 (C-2), 129.6 (C-15, C-19), 130.2 (C-12), 130.6 (C-6), 132.6 (C-16, C-18), 138.6 (C-10),
142.9 (C-14), 183.6 (C-13); Anal. Calcd. for C21H11N3O C, 78.49; H, 3.45; N, 13.08. Found C,
78.50; H, 3.42; N, 13.10.
1-(4-methoxybenzoyl)-1,2,3,3a-tetrahydropyrrolo[1,2-a]quinoline-2,3-dicarbonitrile 9a
◦
Yellow powder; yield: 74%; mp 203–204 C; IR (KBr),
ν
max 2972, 2852, 2255, 1690, 1604,
1486, 1314, 1256, 1164, 745 cm−1; 1H-NMR (DMSO-d6)
δ: 3.91 (1H, s, OMe), 4.21 (1H, d, J =
4.0 Hz, H-3), 4.72 (1H, d, J = 9.0 Hz, H-2), 5.12 (1H, bs, H-10), 5.74 (1H, dd, J = 10.0, 1.5 Hz,
H-4), 5.86 (1H, d, J = 8.0 Hz, H-9), 5.89 (1H, d, J = 9.0 Hz, H-1), 6.58 (1H, t, J = 7.5 Hz, H-7),
6.60 (1H, d, J = 10.0 Hz, H-5), 6.93 (2H, t, J = 8.5 Hz, H-8), 6.96 (1H, d, J = 7.5 Hz, H-6), 7.14
(2H, d, J = 8.5 Hz, H-16, H-18), 8.20 (2H, d, J = 8.5 Hz, H-15, H-19); 13C-NMR (DMSO-d6)
δ
: 33.1 (C-2), 40.3 (C-3), 55.8 (OMe), 61.7 (C-10), 62.0 (C-1), 109.8 (C-9), 114.5 (C-16, C-18),