3.5. Spectral data
3.5.1. Ethyl 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-bis(4-isopropylphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (a1):
White solid, M.P.: 230–232°C; IR (KBr) ν: 3242, 2961, 2868, 1645, 1604, 1493, 1368, 1318, 1256, 1176, 1070, 754 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.22 (s, 1H), 7.24–6.85 (m, 12H), 6.58–6.25 (m, 3H), 6.06 (d, J = 8.2 Hz, 2H), 5.05 (s, 1H), 4.39 (d, J = 37.4 Hz, 2H), 2.89 (dd, J = 14.9, 7.8 Hz, 2H), 2.69 (dd, J = 41.3, 10.6 Hz, 2H), 1.46 (t, J = 7.1 Hz, 3H), 1.23 (d, J = 6.4 Hz, 12H); 13C NMR (62.5 MHz, CDCl3) δ = 168.21, 155.59, 148.22, 146.91, 145.57, 140.36, 139.81, 136.45, 128.83, 128.63, 127.22, 126.79, 126.34, 126.14, 120.86, 116.53, 113.90, 98.69, 77.49, 76.98, 76.48, 59.79, 58.19, 54.87, 33.75, 33.56, 33.43, 23.96, 14.72; MS: m/z = 626 [M+], 625 (base peak).
3.5.2. Ethyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-bis(4-isopropylphenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (a2):
White solid, M.P.: 237–240°C; IR (KBr) ν: 3241, 2961, 2869, 1645, 1602, 1489, 1318, 1255, 1067, 1010, 827, 799 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.22 (s, 1H), 7.13 (dq, J = 14.8, 7.7 Hz, 12H), 6.58–6.21 (m, 3H), 6.02 (d, J = 8.1 Hz, 2H), 5.06 (d, J = 5.4 Hz, 1H), 4.63–4.07 (m, 2H), 3.00–2.83 (m, 2H), 2.73 (d, J = 35.8 Hz, 2H), 1.47 (t, J = 7.1 Hz, 3H), 1.23 (d, J = 6.3 Hz, 12H); 13C NMR (62.5 MHz, CDCl3) δ = 168.22, 155.45, 148.24, 146.96, 145.99, 140.28, 139.69, 136.96, 131.83, 131.50, 127.50, 126.81, 126.36, 126.12, 119.99, 119.10, 116.97, 114.49, 108.13, 98.80, 59.82, 58.16, 54.85, 33.77, 33.58, 33.39, 23.97, 14.74; MS: m/z = 714 [M+], 596 (base peak).
3.5.3. Ethyl 2,6-bis(3-nitrophenyl)-1-(p-tolyl)-4-(p-tolylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (a3):
Yellow solid, M.P.: 174–176°C; IR (KBr) ν: 3215, 2974, 2915, 1653, 1593, 1520, 1348, 1317, 1255, 1070, 785, 702 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.27 (s, 1H), 8.30 (s, 1H), 8.09 (d, J = 8.2 Hz, 2H), 7.94 (d, J = 5.7 Hz, 1H), 7.63 (d, J = 7.8 Hz, 1H), 7.45 (q, J = 7.0, 5.2 Hz, 3H), 6.90 (q, J = 7.5, 6.4 Hz, 4H), 6.43 (d, J = 5.6 Hz, 1H), 6.32 (dd, J = 16.7, 7.8 Hz, 4H), 5.27 (d, J = 4.5 Hz, 1H), 4.62–4.23 (m, 2H), 2.85 (d, J = 4.3 Hz, 2H), 2.27 (s, 3H), 2.17 (s, 3H), 1.51 (t, J = 7.2 Hz, 3H); 13C NMR (62.5 MHz, CDCl3) δ = 167.69, 155.61, 148.62, 146.70, 144.72, 143.57, 136.45, 134.52, 132.64, 132.35, 129.82, 129.66, 129.18, 126.77, 125.67, 122.37, 121.71, 121.43, 113.17, 96.45, 60.13, 57.02, 55.32, 33.66, 20.86, 20.09, 14.77; MS: m/z = 592 [M+], 591 (base peak).
3.5.4. Methyl 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-bis(3-nitrophenyl)-1,2,5,6-tetra- hydropyridine-3-carboxylate (a4):
White solid, M.P.: 201–203°C; IR (KBr) ν: 3224, 3073, 2949, 1660, 1605, 1524, 1493, 1349, 1320, 1258, 1190, 803, 733 cm− 1; 1H NMR (250 MHz, CDCl3) δ = 10.28 (s, 1H), 8.46–7.82 (m, 4H), 7.82–7.33 (m, 4H), 7.33–6.89 (m, 4H), 6.61–6.14 (m, 5H), 5.30 (s, 1H), 3.99 (s, 3H), 2.86 (m, J = 5.7, 3.0 Hz, 2H); 13C NMR (62.5 MHz, CDCl3) δ = 167.88, 154.74, 148.61, 145.56, 144.23, 143.82, 135.64, 132.37, 129.85, 129.36, 129.21, 126.66, 122.90, 122.73, 122.08, 121.31, 114.24, 97.29, 57.01, 55.32, 51.60, 33.65; MS: m/z = 618 [M+], 581 (base peak).
3.5.5. Ethyl 1,2,6-triphenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (a5):
White solid, M.P.: 174–176°C; IR (KBr) ν: 3248, 3457, 2981, 2872, 1652, 1593, 1500, 1373, 1252, 1172, 1070, 750, 699 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.29 (s, 1H), 7.32 (s, 6H), 7.22–6.96 (m, 8H), 6.71–6.39 (m, 5H), 6.37–6.11 (m, 2H), 5.14 (d, J = 5.1 Hz, 1H), 4.63–4.19 (m, 2H), 3.00-2.64 (m, 2H), 1.47 (t, J = 7.1 Hz, 3H).
3.5.6. Ethyl 2,6-bis(4-chlorophenyl)-1-phenyl-4-(phenylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate (a6):
Cream solid, M.P.: 237–239 ˚C; IR (KBr) ν: 3238, 3060, 2978, 2872, 1650, 1595, 1500, 1368, 1251, 1175, 1067, 748, 691 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.30 (s, 1H), 7.39–7.01 (m, 13H), 6.65 (t, J = 7.2 Hz, 1H), 6.57–6.31 (m, 5H), 5.09 (d, J = 4.3 Hz, 1H), 4.59–4.16 (m, 2H), 2.79 (dd, J = 8.3, 4.2 Hz, 2H), 1.45 (t, J = 5.9, 4.6 Hz, 3H).
3.5.7. Ethyl 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydro-pyridine-3-carboxylate (a7):
White solid, M.P.: 221–224°C; IR (KBr) ν: 3241, 3093, 2978, 2856, 1646, 1603, 1493, 1372, 1255, 1178, 1071, 727, 698 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.24 (s, 1H), 7.38 (s, 4H), 7.27–6.93 (m, 9H), 6.59–6.28 (m, 4H), 6.17 (d, J = 8.2 Hz, 2H), 5.12 (s, 1H), 4.40 (ddt, J = 28.2, 10.8, 6.2 Hz, 2H), 2.99–2.57 (m, 2H), 1.47 (t, J = 7.1 Hz, 3H).
3.5.8. Ethyl 1,2,6-tris(4-chlorophenyl)-4-((4-chlorophenyl)amino)-1,2,5,6-tetrahydropyridine-3-carboxylate (a8):
White solid, M.P.: 215–218°C; IR (KBr) ν: 3238, 3068, 2982, 2968, 1653, 1601, 1495, 1369, 1330, 1256, 1090, 810 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.25 (s, 1H), 7.33 (s, 1H), 7.26–6.94 (m, 11H), 6.33 (dd, J = 16.6, 7.6 Hz, 5H), 5.06 (d, J = 5.0 Hz, 1H), 4.39 (dq, J = 25.4, 9.2 Hz, 2H), 2.91–2.56 (m, 2H), 1.45 (t, J = 7.2 Hz, 3H).
3.5.9. Ethyl 1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-2,6-bis(3-nitrophenyl)-1,2,5,6-tetra-hydropyridine-3-carboxylate (a9):
Yellow solid, M.P.: 175–178°C; IR (KBr) ν: 3241, 3178, 2976, 2865, 1655, 1592, 1522, 1496, 1350, 1247, 1176, 1067, 810, 732 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.34 (s, 1H), 8.38–7.88 (m, 4H), 7.70–7.35 (m, 4H), 7.20–6.91 (m, 4H), 6.41 (s, 1H), 6.40–6.21 (m, 4H), 5.30 (s, 1H), 4.68–4.24 (m, 2H), 2.86 (t, J = 4.9 Hz, 2H), 1.52 (t, J = 7.1 Hz, 3H).
3.5.10. Ethyl 2,6-bis(3-bromophenyl)-1-(4-chlorophenyl)-4-((4-chlorophenyl)amino)-1,2,5,6-tetrahydropyridine-3-carboxylate (a10):
White solid, M.P.: 211–213°C; IR (KBr) ν: 3241, 3178, 2976, 2865, 1655, 1592, 1522, 1496, 1350, 1247, 1176, 1067, 810, 732 cm-1
3.5.11. Ethyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydro-pyridine-3-carboxylate (a11):
White solid, M.P.: 223–227°C; IR (KBr) ν: 3241, 3087, 2973, 2859, 1646, 1602, 1491, 1372, 1251, 1068, 1011, 800, 719 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.23 (s, 1H), 7.39–7.07 (m, 14H), 6.39 (d, J = 7.3 Hz, 3H), 6.11 (d, J = 8.2 Hz, 2H), 5.09 (s, 1H), 4.41 (dqd, J = 26.7, 10.7, 7.1, 6.3 Hz, 2H), 2.93–2.63 (m, 2H), 1.46 (t, J = 7.1 Hz, 3H).
3.5.12. Ethyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-bis(4-chlorophenyl)-1,2,5,6-tetrahydropyridine-3-carboxylate (a12):
White solid, M.P.: 202–205°C; IR (KBr) ν: 3229, 3068, 2979, 1654, 1590, 1487, 1370, 1250, 1176, 1091, 805, 720 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.25 (s, 1H), 7.32-7.00 (m, 12H), 6.43–6.18 (m, 5H), 5.05 (s, 1H), 4.58–4.17 (m, 2H), 2.92–2.59 (m, 2H), 1.44 (t, J = 7.1 Hz, 3H).
3.5.13. Ethyl 1-(4-bromophenyl)-4-((4-bromophenyl)amino)-2,6-bis(3-nitrophenyl)-1,2,5,6-tetra-hydropyridine-3-carboxylate (a13):
White solid, M.P.: 180–183°C; IR (KBr) ν: 3232, 3068, 2985, 2865, 1662, 1609, 1529, 1349, 1247, 1175, 1068, 805, 731 cm-1
3.5.14. Ethyl 2,6-bis(3-bromophenyl)-1-(4-bromophenyl)-4-((4-bromophenyl)amino)-1,2,5,6-tetrahydropyridine-3-carboxylate (a14):
White solid, M.P.: 218–220°C; IR (KBr) ν: 3226, 3153, 2985, 1647, 1588, 1490, 1369, 1254, 1067, 1011, 807, 785 cm-1
3.5.15. Ethyl 1-(4-iodophenyl)-4-((4-iodophenyl)amino)-2,6-diphenyl-1,2,5,6-tetrahydropyridine − 3-carboxylate (a15):
White solid, M.P.: 234–237°C; IR (KBr) ν: 3233, 3059, 2983, 2872, 1648, 1600, 1497, 1317, 1251, 1183, 1073, 796, 698 cm-1; 1H NMR (250 MHz, CDCl3) δ = 10.25 (s, 1H), 7.54–7.27 (m, 11H), 7.25–7.07 (m, 3H), 6.51–6.24 (m, 3H), 5.99 (d, J = 8.1 Hz, 2H), 5.12 (s, 1H), 4.59–4.22 (m, 2H), 3.00-2.64 (m, 2H), 1.47 (t, J = 7.1 Hz, 3H).
White solid, M.P.: 126–128°C; IR (KBr) ν: 3035, 2944, 2859, 1669, 1513, 1374, 1339, 1217, 820, 747 cm-1; 1H NMR (250 MHz, CDCl3) δ = 7.49–6.81 (m, 8H), 6.02 (s, 1H), 3.92 (q, J = 15.7 Hz, 2H), 2.29 (s, 3H), 2.25 (s, 3H). 13C NMR (62.5 MHz, CDCl3) δ 171.04, 138.75, 136.96, 136.61, 134.87, 129.71, 129.50, 126.86, 125.63, 65.52, 33.43, 21.15, 20.99; MS: m/z = 283 [M+], 283 (base peak).
White solid, M.P.: 209–213°C; IR (KBr) ν: 3250, 3034, 2905, 2872, 1662, 1602, 1512, 1461, 1387, 1242, 813, 746 cm-1; 1H NMR (250 MHz, CDCl3) δ = 7.25 (d, J = 2.6 Hz, 2H), 7.16–7.01 (m, 4H), 6.86–6.68 (m, 2H), 5.97 (s, 1H), 5.15 (s, 1H), 4.07–3.74 (m, 2H), 2.26 (s, 3H). 13C NMR (63 MHz, CDCl3) δ 171.10, 149.99, 130.08, 129.75, 125.43, 119.21, 115.96, 113.49, 65.40, 33.29, 20.94; MS: m/z = 285 [M+], 137 (base peak).
White solid, M.P.: 169–170°C; IR (KBr) ν: 3057, 3031, 2939, 1669, 1513, 1378, 1219, 805, 749 cm-1; 1H NMR (250 MHz, CDCl3) δ = 7.24 (s, 4H), 7.04 (q, J = 8.0 Hz, 4H), 6.03 (s, 1H), 4.08–3.76 (m, 2H), 2.25 (s, 3H).
Yellow solid, M.P.: 150–152°C; IR (KBr) ν: 3050, 3021, 2922, 1670, 1530, 1391, 1351, 1219, 807, 725 cm-1; 1H NMR (250 MHz, CDCl3) δ = 8.26–7.98 (m, 1H), 7.75–7.37 (m, 1H), 7.19–6.89 (m, 1H), 6.16 (s, 0H), 4.17–3.79 (m, 1H), 2.25 (s, 1H).
White solid, M.P.: 127–129°C; IR (KBr) ν: 3034, 2938, 1669, 1379, 1348, 1216, 726 cm-1
White solid, M.P.: 137–140°C; IR (KBr) ν: 3037, 2975, 2922, 2899, 2852, 1697, 1512, 1354, 809, 740 cm-1
White solid, M.P.: 107–111°C; IR (KBr) ν: 3030, 2971, 2925, 2859, 1690, 1587, 1510, 1364, 818, 501 cm-1
Yellow solid, M.P.: 159–163°C; IR (KBr) ν: 3030, 2964, 2912, 1670, 1590, 1514, 1392, 1329, 1217, 748 cm-1
White solid, M.P.: 226–228°C; IR (KBr) ν: 3037, 2971, 2928, 1666, 1513, 1379, 1221, 818, 737 cm-1
White solid, M.P.: 216–218°C; IR (KBr) ν: 3214, 3118, 2984, 1606, 1520, 1464, 1379, 1333, 833, 772 cm-1