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Pyrano[3,2-c]quinolines 3 and 4; General Procedure.
To a mixture of aldehyde 1 (2 mmol), aniline 2 (2 mmol), and 2,3-dihydropyran (4 mmol) in CH3CN (10 mL) was added iodine (0.15 g, 30 mol%) and the solution was stirred at r.t.
for the appropriate time (Table
[3]
). To the reaction mixture was added 10% aq NaS2O3 soln (20 mL) and the product was extracted with CH2Cl2 (2 × 10 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and the solvent was evaporated. The residue was purified by silica gel
column chromatography with petroleum ether (60-90 °C)-EtOAc (95:5) as the eluent to
afford the pure compounds.
3a: white solid; mp 131-133 °C (Lit.
[12]
130-132 °C).
IR (KBr): 3373, 3055, 3027, 2938, 2856, 1610, 1492, 1365, 1306, 1265, 1071, 913, 749,
702 cm-1.
1H NMR (400MHz, CDCl3): δ = 1.27-1.53 (4 H, m), 2.18 (1 H, m), 3.61-3.88 (3 H, m), 4.66 (1 H, d, J = 2.6 Hz), 5.33 (1 H, d, J = 5.6 Hz), 6.58 (1 H, d, J = 7.8 Hz), 6.78 (1 H, t, J = 7.6 Hz), 7.03 (1 H, t, J = 7.6 Hz), 7.28-7.47 (6 H, m).
MS: m/z (%) = 265 (M+, 77), 206 (100).
4a: yellowish viscous liquid.
IR (neat film): 3378, 3061, 2945, 2857, 1612, 1499, 1366, 1271, 1072, 913, 756, 708
cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.27 (1 H, m), 1.58 (1 H, m), 1.69 (1 H, m), 1.85 (1 H, m), 2.15 (1 H, m),
3.76 (1 H, dt, J = 2.5, 11.6 Hz), 4.11 (2 H, m), 4.43 (1 H, d, J = 2.7 Hz), 4.76 (1 H, d, J = 10.8 Hz), 6.59 (1 H, d, J = 7.4 Hz), 6.73 (1 H, t, J = 7.2 Hz), 7.11 (1 H, t, J = 7.2 Hz), 7.27 (1 H, d, J = 7.4 Hz), 7.39-7.46 (5 H, m).
MS: m/z (%) = 265 (M+, 100), 207 (69).
3b: white solid; mp 171-172 °C (Lit.
[12]
170-172 °C).
IR (KBr): 3389, 3078, 3027, 2920, 2855, 1605, 1512, 1321, 1277, 818 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.26-1.31 (1 H, m), 1.42- 1.51 (3 H, m), 2.03-2.13 (1 H, m), 3.37-3.42 (1 H,
m), 3.58-3.61 (1 H, m), 3.81-3.93 (1 H, br), 4.64 (1 H, d, J = 2.4 Hz), 5.25 (1 H, d, J = 5.6 Hz), 6.51 (1 H, d, J = 8 Hz), 7.02 (1 H, dd, J = 8.0, 2.4 Hz), 7.28-7.38 (6 H, m).
MS: m/z (%) = 299 (M+, 100), 241 (48).
4b: pale solid; mp 129-131 °C (Lit.
[12]
125-126 °C).
IR (KBr): 3383, 3066, 3027, 2921, 2867, 1607, 151, 1366, 1265, 1079, 824 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.33-1.37 (1 H, m), 1.45-1.49 (1 H, m), 1.60-1.68 (1 H, m), 1.81-1.84 (1 H,
m), 2.04-2.08 (1 H, m), 3.71 (1 H, dt, J = 2.6, 7.6 Hz), 4.06-4.10 (1 H, m), 4.34 (1 H, d, J = 2.8 Hz), 4.67 (1 H, d, J = 10.8 Hz), 6.46 (1 H, d, J = 8.4 Hz), 7.03 (1 H, dt, J = 8.4, 2.4 Hz), 7.21 (1 H, d, J = 2.4 Hz), 7.32-7.41 (5 H, m).
MS: m/z (%) = 299 (M+, 67), 241 (100).
3c: white solid; mp 146-147 °C (Lit.
[12]
144-146 °C).
IR (KBr): 3340, 3051, 2970, 2860, 1610, 1520, 1365, 1270, 1065, 837, 776 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.25-1.33 (1 H, m), 1.45-1.55 (3 H, m), 2.12-2.18 (1 H, m), 3.41-3.46 (1 H,
m), 3.58 (1 H, m), 3.77 (3 H, s), 4.62 (1 H, d, J = 2.4 Hz), 5.30 (1 H, d, J = 5.6 Hz), 6.57 (1 H, d, J = 9.2 Hz), 6.71 (1 H, dd, J = 6.4, 1.8 Hz), 7.03 (1 H, dd, J = 2.9, 0.8 Hz), 7.29-7.43 (5 H, m).
MS: m/z (%) = 295 (M+, 100), 237 (33).
4c: pale solid; mp 97-99 °C (Lit.
[12]
98-100 °C).
IR (KBr):3340, 3021, 2975, 2845, 160, 1495, 1260, 1080, 845 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.31-1.35 (1 H, m), 1.45-1.48 (1 H, m), 1.62-1.67 (1 H, m), 1.78-1.85 (1 H,
m), 2.06-2.11 (1 H, m), 3.46-3.55 (1 H, br), 3.70 (1 H, dt, J = 2.6, 7.0 Hz), 3.75 (3 H, s), 4.10 (1 H, dt, J = 11.2, 2.2 Hz), 4.36 (1 H, d, J = 2.8 Hz), 4.65 (1 H, d, J = 10.4 Hz), 6.49 (1 H, d, J = 8.8 Hz), 6.74 (1 H, dd, J = 8.8, 2.9 Hz), 6.81 (1 H, d, J = 2.8 Hz), 7.30-7.43 (5 H, m).
MS: m/z (%) = 295 (M+, 58), 237 (100).
3d: white solid; mp 143-144 °C (Lit.
[21]
142-143 °C).
IR (KBr): 3366, 3023, 2933, 2859, 1617, 1499, 1454, 1352, 1307, 1258, 1082, 808, 698
cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.27-1.32 (1 H, m), 1.42-1.55 (3 H, m), 2.15 (1 H, m), 2.27 (3 H, s), 3.44
(1 H, dt, J = 2.4, 7.0 Hz), 3.60 (1 H, m), 4.64 (1 H, d, J = 2.2 Hz), 5.30 (1 H, d, J = 5.6 Hz), 6.52 (1 H, d, J = 8.0 Hz), 6.91 (1 H, d, J = 8.0 Hz), 7.24 (1 H, s), 7.29-7.42 (5 H, m).
MS: m/z (%) = 279 (M+, 100), 220 (30).
4d: white solid; mp 89-91 °C.
IR (KBr): 3378, 3045, 2967, 2855, 1613, 1505, 1334, 1267, 1078, 826 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.24-1.27 (1 H, m), 1.30-1.34 (1 H, m), 1.43-1.50 (1 H, m), 1.61-1.69 (1 H,
m), 2.06-2.09 (1 H, m), 2.23 (3 H, s), 3.69-3.74 (1 H, m), 4.08-4.11 (1 H, m), 4.36
(1 H, d, J = 2.7 Hz), 4.68 (1 H, d, J = 10.8 Hz), 6.45 (1 H, d, J = 8.0 Hz), 6.90 (1 H, dd, J = 8.0, 1.7 Hz), 7.04 (1 H, d, J = 1.0 Hz), 7.31-7.43 (5 H, m).
MS: m/z (%) = 279 (M+, 100), 221 (82).
3e: white solid; mp 147-148 °C (Lit.
[12]
143-144 °C).
IR (KBr): 3338, 3023, 2933, 2864, 1601, 1474, 1348, 1303, 1270, 1086, 1037, 759, 702
cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.24-1.33 (1 H, m), 1.40-1.55 (3 H, m), 2.14-2.17 (4 H, m), 3.42 (1 H, m),
3.55-3.59 (1 H, m), 3.69 (1 H, br), 4.70 (1 H, d, J = 2.4 Hz), 5.36 (1 H, d, J = 5.6 Hz), 6.74 (1 H, t, J = 7.2 Hz), 7.00 (1 H, d, J = 7.2 Hz), 7.32-7.47 (6 H, m).
MS: m/z (%) = 279 (M+, 100), 220 (52).
4e: white solid; mp 128-129 °C (Lit.
[12]
130-132 °C).
IR (KBr): 3387, 3060, 3027, 2933, 2876, 2827, 1601, 1474, 1364, 1254, 1053, 747, 706
cm-1.
1H NMR (400MHz, CDCl3): δ = 1.30-1.36 (1 H, m), 1.44-1.50 (1 H, m), 1.62-1.69 (1 H, m), 1.82-1.90 (1 H,
m), 2.05 (3 H, s), 2.07-2.11 (1 H, m), 3.72 (1 H, dt, J = 2.4, 11.6 Hz), 4.11 (1 H, dt, J = 11.2, 2.2 Hz), 4.39 (1 H, d, J = 2.6 Hz), 4.75 (1 H, d, J = 11.2 Hz), 6.65 (1 H, t, J = 7.2 Hz), 7.00 (1 H, d, J = 7.2 Hz), 7.12 (1 H, d, J = 7.6 Hz), 7.33-7.46 (5 H, m).
MS: m/z (%) = 279 (M+, 100), 221 (80).
4g′: white solid; mp 155-156 °C.
IR (KBr): 3411, 3035, 2937, 2847, 1597, 1499, 1474, 1433, 1307, 1123, 1053, 918, 796,
735, 702 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.33 (1 H, d, J = 13.2 Hz), 1.49 (1 H, dd, J = 13.8, 2 Hz), 1.66-1.73 (1 H, m), 1.89-1.95 (1 H, m), 2.02 (1 H, d, J = 11.5 Hz), 3.73 (1 H, dt, J = 2.4, 12 Hz), 4.13 (1 H, dd, J = 11.6, 4.8 Hz), 4.69 (1 H, s), 4.86 (1 H, d, J = 11.6 Hz), 6.65 (1 H, d, J = 8.0 Hz), 6.98 (1 H, d, J = 7.6 Hz), 7.13 (1 H, t, J = 8.0 Hz), 7.32-7.43 (5 H, m).
MS: m/z (%) = 333 (M+, 38), 275 (100).
3h: white solid; mp 126-128 °C.
IR (KBr): 3366, 3019, 2941, 2859, 1609, 1477, 1352, 1315, 1213, 1090, 1029, 927, 816,
751 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.29-1.34 (1 H, m), 1.42-1.55 (3 H, m), 2.13 (1 H, m), 2.36 (3 H, s), 3.43
(1 H, m), 3.56-3.60 (1 H, m), 4.65 (1 H, d, J = 2.4 Hz), 5.31 (1 H, d, J = 5.6 Hz), 6.58 (1 H, d, J = 8.0 Hz), 6.78 (1 H, t, J = 7.6 Hz), 7.08 (1 H, dt, J = 0.6, 8.0 Hz), 7.18 (2 H, d, J = 8.0 Hz), 7.29 (2 H, d, J = 8.0 Hz), 7.41 (1 H, d, J = 7.6 Hz).
MS: m/z (%) = 279 (M+, 100), 221 (73).
4h: white solid; mp 123-125 °C.
IR (KBr): 3370, 3019, 2937, 2855, 1609, 1491, 1372, 1307, 1262, 1078, 812, 743 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.33 (1 H, m), 1.50 (1 H, m), 1.63 (1 H, m), 1.88 (1 H, m), 2.08 (1 H, m),
2.36 (3 H, s), 3.70 (1 H, dt, J = 2.5, 11.6 Hz), 4.09 (1 H, dt, J = 10.8, 2.6 Hz), 4.37 (1 H, d, J = 2.7 Hz), 4.67 (1 H, d, J = 10.8 Hz), 6.50 (1 H, d, J = 8.0 Hz), 6.69 (1 H, dt, J = 1.0, 7.2 Hz), 7.06 (1 H, dt, J = 1.6, 8.0 Hz), 7.16-7.23 (3 H, m), 7.30 (2 H, d, J = 8.0 Hz).
MS: m/z (%) = 279 (M+, 100), 221 (35).
3i: white solid; mp 168-170 °C.
IR (KBr): 3346, 3051, 2941, 2859, 1605, 1482, 1315, 1262, 1060, 755, 620, 489 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.26-1.33 (1 H, m), 1.44-1.54 (3 H, m), 2.15 (1 H, m), 3.42 (1 H, m), 3.57-3.61
(1 H, m), 4.64 (1 H, d, J = 2.4 Hz), 5.30 (1 H, d, J = 5.5 Hz), 6.60 (1 H, d, J = 7.4 Hz), 6.80 (1 H, dt, J = 0.8, 7.4 Hz), 7.08 (1 H, t, J = 7.4 Hz), 7.29 (2 H, d, J = 8.4 Hz), 7.42 (1 H, d, J = 8.0 Hz), 7.50 (2 H, dd, J = 6.8, 1.8 Hz).
MS: m/z (%) = 235 (M + 1, 25), 286 (100).
4i: white solid; mp 131-133 °C.
IR (KBr): 3358, 3015, 2937, 2847, 1609, 1495, 1364, 1266, 1078, 1033, 1008, 841, 816,
747, 465 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.32-1.36 (1 H, m), 1.41-1.47 (1 H, m), 1.62-1.68 (1 H, m), 1.74-1.83 (1 H,
m), 2.01-2.05 (1 H, m), 3.71 (1 H, dt, J = 2.4, 11.6 Hz), 4.09 (1 H, dt, J = 11.2, 2.1 Hz), 4.37 (1 H, d, J = 2.7 Hz), 4.67 (1 H, d, J = 10.8 Hz), 6.52 (1 H, d, J = 8.0 Hz), 6.71 (1 H, dt, J = 1.0, 7.6 Hz), 7.09 (1 H, t, J = 7.2 Hz), 7.21 (1 H, dd, J = 1.3, 7.6 Hz), 7.29 (2 H, dd, J = 1.6, 8.4 Hz), 7.48 (2 H, dd, J = 1.7, 8.4 Hz).
MS: m/z (%) = 235 (M + 1, 29), 286 (100).
3j: white solid; mp 165-167 °C.
IR (KBr): 3387, 3072, 3011, 2937, 2847, 1605, 1474, 1315, 1258, 1086, 1029, 743, 702
cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.20-1.25 (1 H, m), 1.44-1.49 (1 H, m), 1.52-1.58 (2 H, m), 2.39-2.42 (1 H,
m), 3.42 (1 H, dt, J = 2.3, 11.6 Hz), 3.56-3.61 (1 H, m), 5.06 (1 H, d, J = 2.1 Hz), 5.33 (1 H, d, J = 5.6 Hz), 6.61 (1 H, d, J = 7.6 Hz), 6.80 (1 H, t, J = 7.6 Hz), 7.09 (1 H, t, J = 7.6 Hz), 7.23-7.29 (2 H, m), 7.38-7.45 (2 H, m), 7.65 (1 H, dd, J = 1.5, 7.6 Hz).
MS: m/z (%) = 299 (M+, 70), 241 (100).
4j: colorless viscous liquid.
IR (neat film): 3358, 3056, 3019, 2941, 2855, 1613, 1491, 1364, 1319, 1260, 1082,
755 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.40-1.49 (2 H, m), 1.67-1.74 (1 H, m), 1.86-1.94 (1 H, m), 2.18-2.22 (1 H,
m), 3.6 (1 H, dt, J = 2.8, 11.6 Hz), 3.96-4.00 (1 H, m), 4.43 (1 H, d, J = 3.1 Hz), 5.17 (1 H, d, J = 9.3 Hz), 6.52 (1 H, d, J = 8.0 Hz), 6.73 (1 H, t, J = 7.4 Hz), 7.20 (1 H, t, J = 8.0 Hz), 7.20-7.25 (3 H, m), 7.36 (1 H, dd, J = 1.2, 7.6 Hz), 7.48 (1 H, d, J = 7.6 Hz).
MS: m/z (%) = 299 (M+, 40), 241 (100).
3k: yellow solid; mp 181-183 °C.
IR (KBr): 3407, 3076, 3011, 2987, 2856, 1601, 1530, 1477, 1266, 1078, 886, 784, 698
cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.20 (1 H, m), 1.44-1.60 (3 H, m), 2.19-2.22 (1 H, m), 3.44 (1 H, dt, J = 2.5, 11.2 Hz), 3.60 (1 H, dt, J = 11.6, 2.0 Hz), 3.83 (1 H, br), 4.80 (1 H, d, J = 2.3 Hz), 5.34 (1 H, d, J = 5.6 Hz), 6.66 (1 H, d, J = 8.0 Hz), 6.85 (1 H, t, J = 8.0 Hz), 7.13 (1 H, t, J = 7.6 Hz), 7.44 (1 H, d, J = 8.0 Hz), 7.56 (1 H, t, J = 8.0 Hz), 7.76 (1 H, d, J = 8.0 Hz), 8.17 (1 H, dd, J = 1.5, 8.0 Hz), 8.33 (1 H, s).
MS: m/z (%) = 310 (M+, 53), 251 (100).
4k: yellow solid; mp 159-161 °C.
IR (KBr): 3417, 3056, 2966, 2887, 1604, 1534, 1491, 1345, 1277, 1080, 874, 778, 702
cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.40 (2 H, m), 1.67-1.74 (1 H, m), 1.79-1.86 (1 H, m), 2.12 (1 H, m), 3.74
(1 H, t, J = 11.2 Hz), 4.11 (1 H, d, J = 9.2 Hz), 4.40 (1 H, d, J = 2.5 Hz), 4.83 (1 H, d, J = 10.8 Hz), 6.57 (1 H, d, J = 8.0 Hz), 6.75 (1 H, t, J = 7.6 Hz), 7.12 (1 H, t, J = 7.6 Hz), 7.24 (1 H, d, J = 7.6 Hz), 7.55 (1 H, t, J = 8.0 Hz), 7.76 (1 H, d, J = 7.3 Hz), 8.18 (1 H, dd, J = 1.9, 8.0 Hz), 8.31 (1 H, s)
MS: m/z (%) = 310 (M+, 52), 251 (100).
4l: white solid; mp 134-135 °C.
IR (KBr): 3387, 3039, 2941, 2892, 2835, 1609, 1495, 1368, 1241, 1057, 767 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.30-1.33 (1 H, m), 1.47-1.52 (1 H, m), 1.61-1.67 (1 H, m), 1.78-1.85 (1 H,
m), 2.06 (1 H, m), 3.71 (1 H, dt, J = 2.4, 11.6 Hz), 4.10 (1 H, dt, J = 11.2, 2.2 Hz), 4.38 (1 H, d, J = 2.6 Hz), 4.68 (1 H, d, J = 10.8 Hz), 6.51 (1 H, d, J = 8.0 Hz), 6.70 (1 H, t, J = 7.2 Hz), 6.90 (2 H, d, J = 8.4 Hz), 7.08 (1 H, dt, J = 1.4, 8.0 Hz), 7.21 (1, dd, J = 1.1, 7.6 Hz), 7.34 (2 H, d, J = 8.4 Hz)
MS: m/z (%) = 295 (M+, 100), 236 (182).
3m: white solid; mp 187-189 °C.
IR (KBr): 3382, 3068, 2941, 2868, 1601, 1486, 1274, 1082, 841, 808 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.25-1.28 (1 H, m), 1.44-1.50 (3 H, m), 2.10 (1 H, m), 3.40-3.46 (1 H, m),
3.59-3.63 (1 H, m), 4.63 (1 H, d, J = 2.4 Hz), 5.24 (1 H, d, J = 5.6 Hz), 6.53 (1 H, d, J = 8.6 Hz), 7.03 (1 H, dd, J = 2.2, 8.4 Hz), 7.31-7.36 (4 H, m), 7.38 (1 H, d, J = 1.4 Hz).
MS: m/z (%) = 333 (M+, 53), 274 (100).
4m: white solid; mp 154-156 °C.
IR (KBr): 3346, 2933, 2847, 1613, 1491, 1268, 1033, 882, 812 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.32-1.38 (1 H, m), 1.43-1.47 (1 H, m), 1.63-1.69 (1 H, m), 1.75-1.82 (1 H,
m), 2.04 (1 H, m), 3.70 (1 H, dt, J = 2.4, 11.6 Hz), 4.07 (1 H, d, J = 11.6 Hz), 4.34 (1 H, d, J = 2.7 Hz), 4.67 (1 H, d, J = 10.8 Hz), 6.46 (1 H, d, J = 8.4 Hz), 7.04 (1 H, dd, J = 2.4, 8.8 Hz), 7.21 (1 H, d, J = 2.3 Hz), 7.35 (4 H, m).
MS: m/z (%) = 333 (M+, 55), 274 (100).
4n: white solid; mp 151-153 °C.
IR (KBr): 3346, 3035, 3002, 2970, 2941, 2884, 2839, 1609, 1511, 1462, 1298, 1241,
1172, 1045, 890, 824 cm-1.
1H NMR (400 MHz, CDCl3): δ = 1.33-1.38 (1 H, m), 1.45-1.52 (1 H, m), 1.63 (1 H, m), 1.78-1.84 (1 H, m),
2.05-2.11 (1 H, m), 3.71 (1 H, dt, J = 2.4, 11.2 Hz), 3.75 (3 H, s), 3.83 (3 H, s), 4.36 (1 H, d, J = 2.7 Hz), 4.62 (1 H, d, J = 10.8 Hz), 6.48 (1 H, d, J = 8.8 Hz), 6.72 (1 H, dd, J = 2.8, 8.8 Hz), 6.81 (1 H, d, J = 2.8 Hz), 6.90 (2 H, d, J = 8.4 Hz), 7.34 (2 H, d, J = 8.4 Hz).
MS: m/z (%) = 325 (M+, 100), 266 (30).