ACCEPTED MANUSCRIPT
1-Benzyl-2-ferrocenyl-2,3-dihydroquinolin-4(1H)-one (15a). Yield (75%), m.p. 105 °C;
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IR (KBr): ν = 2924, 2877, 1666, 1603, 1488, 1224, 745 cm-1; H NMR (200 MHz, CDCl3,
ppm): δ 7.92 (dd, J = 7.8, 1.8 Hz, 1H), 7.39 – 7.15 (m, 6H), 6.69 – 6.61 (m, 1H), 6.46 (d, J =
8.6 Hz, 1H), 4.63 (d, J = 16.8 Hz, 1H), 4.59 (dd, J = 6.0, 4.0 Hz, 1H), 4.45 (d, J = 16.8 Hz,
1H), 4.15 (s, 5H), 4.10 – 4.06 (m, 4H), 3.34 (dd, J = 16.2, 6.0 Hz, 1H), 3.22 (dd, J = 16.2, 4.0
Hz, 1H); 13C NMR (50 MHz, CDCl3, ppm): δ = 193.2, 149.4, 137.8, 135.6, 128.8, 127.6,
127.2, 126.5, 119.7, 116.6, 113.7, 86.7, 68.8, 68.6, 67.6, 66.7, 58.6, 53.3, 44.0.
2-Ferrocenyl-1-(4-methylbenzyl)-2,3-dihydroquinolin-4(1H)-one (15b). Yield (90%), m.p.
111 °C; IR (KBr): ν = 2916, 1672, 1601, 1489, 1224, 759 cm-1. 1H NMR (200 MHz, CDCl3,
ppm): δ = 7.91 (dd, J = 7.8, 1.7 Hz, 1H), 7.24 – 7.11 (m, 5H), 6.67 – 6.59 (m, 1H), 6.47 (d, J
= 8.5 Hz, 1H), 4.60 (d, J = 16.5 Hz, 1H), 4.57 (dd, J = 5.9, 4.0 Hz, 1H), 4.40 (d, J = 16.5 Hz,
1H), 4.14 (s, 5H), 4.10 – 4.06 (m, 4H), 3.31 (dd, J = 16.2, 5.9 Hz, 1H), 3.20 (dd, J = 16.2, 4.0
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Hz, 1H), 2.34 (s, 3H). C NMR (50 MHz, CDCl3, ppm): δ = 193.2, 149.5, 136.8, 135.5,
134.6, 129.4, 127.5, 126.4, 119.7, 116.4, 113.6, 86.7, 68.8, 68.6, 68.5, 67.6, 66.7, 58.4, 52.9,
43.9, 21.0.
1-(4-Bromobenzyl)-2-ferrocenyl-2,3-dihydroquinolin-4(1H)-one (15c). Yield (63%), m.p.
132 °C; IR (KBr): ν = 2876, 1674, 1601, 1484, 1223, 755 cm-1; 1H NMR (200 MHz, CDCl3,
ppm): δ 7.93 (dd, J = 7.8, 1.7 Hz, 1H), 7.48 – 7.41 (m, 2H), 7.20 (ddd, J = 8.7, 7.2, 1.7 Hz,
1H), 7.17 – 7.10 (m, 2H), 6.68 (ddd, J = 7.8, 7.2, 0.9 Hz, 1H), 6.39 (dd, J = 8.7, 0.9 Hz, 1H),
4.56 (dd, J = 5.8, 4.5 Hz, 1H), 4.55 (d, J = 16.7 Hz, 1H), 4.39 (d, J = 16.7 Hz, 1H), 4.16 (s,
5H), 4.10 – 4.03 (m, 4H), 3.34 (dd, J = 16.2, 5.8 Hz, 1H), 3.23 (dd, J = 16.2, 4.5 Hz, 1H); 13C
NMR (50 MHz, CDCl3, ppm): δ 193.1, 149.2, 136.9, 135.6, 131.9, 128.2, 127.7, 120.9,
119.9, 116.9, 113.7, 86.6, 68.9, 68.7, 68.7, 67.7, 66.7, 58.9, 52.8, 44.1.
1-Benzyl-6-chloro-2-ferrocenyl-2,3-dihydroquinolin-4(1H)-one (15d). Yield (76%), m.p.
140 °C; IR (KBr): ν = 2897, 1680, 1599, 1484, 1215, 811 cm-1; 1H NMR (200 MHz, CDCl3,
ppm): δ = 7.87 (d, J = 2.7 Hz, 1H), 7.40 – 7.22 (m, 5H), 7.12 (dd, J = 9.0, 2.7 Hz, 1H), 6.40
(d, J = 9.0 Hz, 1H), 4.59 (d, J = 16.6 Hz, 1H), 4.59 (dd, J = 5.8, 3.9 Hz, 1H), 4.46 (d, J = 16.6
Hz, 1H), 4.16 (s, 5H), 4.12 – 4.05 (m, 4H), 3.32 (dd, J = 16.3, 5.8 Hz, 1H), 3.22 (dd, J = 16.3,
3.9 Hz, 1H); 13C NMR (50 MHz, CDCl3, ppm): δ = 192.1, 147.8, 137.2, 135.3, 128.9, 127.4,
126.8, 126.4, 122.2, 120.4, 115.4, 86.4, 68.9, 68.7, 68.6, 67.8, 66.6, 58.8, 53.5, 43.8.
6-Chloro-2-ferrocenyl-1-(4-methylbenzyl)-2,3-dihydroquinolin-4(1H)-one (15e). Yield
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(50%), m.p. 114 °C; IR (KBr): ν = 2918, 1668, 1601, 1489, 1213, 805 cm-1; H NMR (200
MHz, CDCl3, ppm): δ = 7.87 (d, J = 2.7 Hz, 1H), 7.16 – 7.13 (m, 4H), 7.12 (dd, J = 9.1, 2.7
Hz, 1H), 6.41 (d, J = 9.1 Hz, 1H), 4.59 (dd, J = 5.6, 4.2 Hz, 1H), 4.56 (d, J = 16.6 Hz, 1H),
4.41 (d, J = 16.6 Hz, 1H), 4.15 (s, 5H), 4.11 – 4.03 (m, 4H), 3.31 (dd, J = 16.3, 5.6 Hz, 1H),
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3.21 (dd, J = 16.3, 4.2 Hz, 1H), 2.35 (s, 3H); C NMR (50 MHz, CDCl3, ppm): δ = 192.2,
147.9, 137.1, 135.3, 134.1, 129.6, 126.8, 126.4, 122.1, 120.4, 115.4, 86.4, 68.9, 68.7, 68.5,
67.8, 66.6, 58.6, 53.2, 43.8, 21.1.
1-(4-Bromobenzyl)-6-chloro-2-ferrocenyl-2,3-dihydroquinolin-4(1H)-one (15f). Yield
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(63%), m.p. 83 °C; IR (KBr): ν = 2919, 1674, 1601, 1487, 1213, 805 cm-1; H NMR (200
MHz, CDCl3, ppm): δ 7.88 (d, J = 2.5 Hz, 1H), 7.45 (d, J = 8.0 Hz, 2H), 7.18 – 7.03 (m, 3H),
6.33 (d, J = 9.0 Hz, 1H), 4.46 – 4.32 (m, 2H), 4.40 (d, J = 17.2 Hz, 1H), 4.26 – 3.99 (m, 4H),
4.18 (s, 5H), 3.42 – 3.09 (m, 2H); 13C NMR (50 MHz, CDCl3, ppm): δ 192.0, 147.6, 136.4,
135.3, 132.0, 128.2, 127.0, 122.6, 121.2, 120.7, 115.4, 86.5, 69.2, 69.0, 68.9, 68.1, 66.8, 59.1,
53.1, 43.9.
1-Benzyl-6-bromo-2-ferrocenyl-2,3-dihydroquinolin-4(1H)-one (15g). Yield (71%), m.p.
131 °C; IR (KBr): ν = 2885, 1671, 1596, 1483, 1213, 740 cm-1; 1H NMR (200 MHz, CDCl3,