Molecules 2019, 24, 1962
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8.0 Hz, 1H), 2.94–2.98 (dd, J = 14.0, 3.6 Hz, 1H), 3.29 (d, J = 16.0 Hz, 1H), 3.55 (d, J = 14.0 Hz, 1H), 4.47
(d, J = 14.0 Hz, 1H), 4.54 (d, J = 10.0 Hz, 1H), 4.76 (d, J = 14.0 Hz, 1H), 5.08–5.11 (td, J = 8.0, 3.6 Hz, 1H),
6.23 (m, 2H), 6.79–8.20 (m, 25H, ArH); 13C-NMR (CDCl3, 100MHz):
δ (ppm) 39.6, 46.8, 48.5, 52.1, 62.1,
66.2, 74.2, 97.9, 120.9, 121.2, 122.3, 122.8, 123.1, 123.8, 124.0, 125.9, 126.3, 126.5, 127.2, 127.9, 128.3, 128.4,
128.5, 129.2, 129.3, 129.4, 130.4, 130.8, 130.9, 131.2, 134.8, 136.5, 137.8, 138.4, 139.8, 140.8, 141.9, 145.6,
154.0, 158.1, 158.5, 163.7, 199.9. LC/MS(ESI): m/z = 870 (M+); Anal. Calcd for C50H38Br2N4O: C, 68.97;
H, 4.40; N, 6.43; Found C, 69.08; H, 4.52; N, 6.51%.
5-Benzyl-spiro-[2.110]-indeno-[1,2-b]quinoxaline-spiro-[3.30]-4-bromo-benzylidine-N-strylpiperidone-4-[4
◦
1
-bromophenyl]-pyrrolidine (8c). Yield 55%; Pale yellow solid: m.p. 165–167 C; H-NMR (CDCl3,
400 MHz): (ppm) 2.33 (d, J = 14.0 Hz, 1H), 2.88–2.92 (dd, J = 14.0, 7.2 Hz, 1H), 3.11–3.16 (m, 2H), 3.34
δ
(d, J = 16.0 Hz, 1H), 3.61 (d, J = 14.0 Hz, 1H), 4.53 (d, J = 14.0 Hz, 1H), 4.61 (d, J = 10.0 Hz, 1H), 4.82
(d, J = 14.0 Hz, 1H), 5.15–5.19 (td, J = 9.0, 3.6 Hz, 1H), 6.10–6.12 (m, 2H), 6.86–8.27 (m, 25H, ArH);
13C-NMR (CDCl3, 100 MHz):
δ (ppm) 40.1, 46.2, 48.2, 52.1, 61.8, 65.6, 74.2, 98.2, 122.1, 123.7, 123.9,
126.4, 127.3, 127.4, 128.5, 128.6, 128.7, 128.8, 129.2, 129.3, 129.4, 129.5, 130.3, 130.9, 131.3, 132.5, 134.5,
136.4, 137.9, 138.4, 139.2, 140.5, 140.8, 141.7, 154.7, 158.5, 160.2, 165.2, 199.1. LC/MS(ESI): m/z = 870
(M+); Anal. Calcd for C50H38Br2N4O: C, 68.97; H, 4.40; N, 6.43; Found C, 69.05; H, 4.53; N, 6.52%.
5-Benzyl-spiro-[2.110]-indeno-[1,2-b]quinoxaline-spiro-[3.30]-2-chloro-benzylidine-N-strylpiperidone-4-[2
-chlorophenyl]-pyrrolidine (8d). Yield 50%; Yellow solid: m.p. 149–151 ◦C; 1H-NMR (CDCl3, 400 MHz):
δ
(ppm) 2.50 (d, J = 14.0 Hz, 1H), 2.62–2.66 (m, 1H), 2.85 (d, J = 14.0 Hz, 1H), 3.05–3.06 (m, 2H), 3.33 (d,
J = 16.0 Hz, 1H), 4.25 (d, J = 14.0 Hz, 1H), 4.49 (d, J = 14.0 Hz, 1H), 4.87 (d, J = 9.5 Hz, 1H), 5.23–5.30
(m, 1H), 6.13–6.14 (m, 2H), 6.74–8.53 (m, 25H, ArH); 13C-NMR (CDCl3, 100MHz):
(ppm) 40.5, 45.7,
δ
51.6, 52.3, 64.2, 65.9, 74.4, 98.9, 122.3, 123.7, 126.2, 126.4, 126.6, 127.0, 128.1, 128.3, 128.9, 129.2, 129.4,
129.6, 129.8, 130.7, 131.3, 132.3, 133.1, 134.9, 135.8, 136.1, 136.2, 136.4, 136.5, 137.7, 138.0, 138.5, 140.5,
141.8, 144.7, 145.8, 154.7, 158.5, 158.6, 162.8, 199.1. LC/MS(ESI): m/z = 781 (M+); Anal. Calcd for
C50H38Cl2N4O: C, 76.82; H, 4.90; N, 7.17; Found C, 76.94; H, 4.99; N, 7.26%.
5-Benzyl-spiro-[2.110]-indeno-[1,2-b]quinoxaline-spiro-[3.30]-2,4-dichloro-benzylidine-N-strylpiperidone-4-[2,
4-dichlrophenyl]-pyrrolidine (8e). Yield 48%; Yellow solid: m.p. 180–182 ◦C; 1H-NMR (CDCl3, 400 MHz):
δ
(ppm) 2.37 (m, 1H), 2.86–2.92 (dd, J = 14.0, 8.0 Hz, 1H), 3.16–3.22 (m, 2H), 3.40 (d, J = 16.0 Hz, 1H),
3.66 (d, J = 14.0 Hz, 1H), 4.54 (d, J = 14.0 Hz, 1H), 4.63 (d, J = 10.0 Hz, 1H), 4.85 (d, J = 14.0 Hz,
1H), 5.20–5.25 (td, J = 8.0, 3.6 Hz, 1H), 6.11–6.12(m, 2H), 6.65–8.51 (m, 25H, ArH); 13C-NMR (CDCl3,
100 MHz):
δ (ppm) 40.3, 46.8, 50.4, 50.9, 63.7, 66.4, 74.5, 98.5, 122.1, 123.8, 126.5, 127.2, 127.4, 128.1,
128.5, 128.9, 129.3, 129.4, 129.5, 129.8, 129.9, 130.7, 131.6, 132.5, 132.6, 134.4, 135.4, 136.1, 136.5, 136.6,
136.9, 137.8, 138.2, 140.2, 141.8, 145.7, 154.7, 158.3, 158.9, 163.8, 196.5. LC/MS(ESI): m/z = 850 (M+); Anal.
Calcd for C50H36Cl4N4O: C, 70.60; H, 4.27; N, 6.59; Found C, 70.73; H, 4.38; N, 6.70%.
5-Benzyl-spiro-[2.110]-indeno-[1,2-b]quinoxaline-spiro-[3.30]-4-chloro-benzylidine-N-strylpiperidone-4-[4
-chlorophenyl]-pyrrolidine (8f). Yield 61%; Yellow solid: m.p. 151–153 ◦C; 1H-NMR (CDCl3, 400MHz):
δ
(ppm) 2.26 (d, J = 14.0 Hz, 1H), 2.77–2.86 (m, 1H), 3.02–3.11(m, 2H), 3.28 (d, J = 16.0 Hz, 1H), 3.56
(d, J = 14.0 Hz, 1H), 4.47 (d, J = 14.0 Hz, 1H), 4.55 (d, J = 10.0 Hz, 1H), 4.76 (d, J = 14.0 Hz, 1H),
5.08–5.14 (td, J = 10.0, 3.6 Hz, 1H), 6.02–6.04 (m, 2H), 6.79–8.20 (m, 25H, ArH); 13C-NMR (CDCl3,
100MHz):
δ (ppm) 39.6, 46.8, 52.6, 52.9, 62.2, 66.6, 72.6, 98.7, 123.8, 124.0, 126.4, 127.2, 127.9, 128.4,
128.8, 128.9, 129.1, 129.2, 129.3, 129.5, 130.7, 130.9, 131.1, 131.3, 132.8, 133.1, 134.7, 135.4, 135.9, 137.3,
137.5, 138.4, 138.5, 141.9, 146.5, 153.8, 158.6, 163.2, 199.7. LC/MS(ESI): m/z = 781 (M+); Anal. Calcd for
C50H38Cl2N4O: C, 76.82; H, 4.90; N, 7.17; Found C, 76.93; H, 4.97; N, 7.28%.
5-Benzyl-spiro-[2.110]-indeno-[1,2-b]quinoxaline-spiro-[3.30]-3-methyl-benzylidine-N-strylpiperidone-4-[2
-methylphenyl]-pyrrolidine (8g). Yield 54%; Yellow solid: m.p. 135–137 ◦C; 1H-NMR (CDCl3, 400MHz):
δ
(ppm) 2.19 (s, 3H), 2.31 (s, 3H), 2.37 (d, J = 14.0 Hz, 1H), 2.78–2.82 (m, 1H), 2.96–3.01 (dd, J = 14.0,
8.0 Hz, 1H), 3.12–3.16 (dd, J = 14.0, 3.5 Hz, 1H), 3.30–3.37 (m, 2H), 4.37 (d, J = 14.0 Hz, 1H), 4.65 (d,
J = 14.0 Hz, 1H), 4.79 (d, J = 9.5 Hz, 1H), 5.35–5.41 (td, J = 9.5, 4.0 Hz, 1H), 6.12–6.14 (m, 2H), 6.67–8.53