PAPER
Liquid-Phase Combinatorial Synthesis of 2,3-Dihydro-4-pyridones
1065
1
3
C NMR (75 MHz, MeOH-d ): d = 193.2, 152.3, 145.7, 132.3,
1-(4-Carboxyphenyl)-2-(3-fluorophenyl)-2,3-dihydro-4-pyri-
done (10f)
4
1
31.3, 130.7, 130.1, 127.6, 126.1, 120.3, 102.4, 62.4, 43.8.
HRMS (MALDI–DHB): m/z calcd for C H NO [M + H+]:
IR (KBr): 3073, 1708, 1585, 1569, 1513, 1489, 1447, 1412, 1365,
1
8
16
3
–1
1
322, 1274, 1220, 1186, 1101, 896, 852, 773, 730, 695 cm .
2
94.1125; found: 294.1127.
1
H NMR (300 MHz, MeOH-d ): d = 8.09 (d, J = 7.5 Hz, 1 H), 7.95
4
1
-(4-Carboxyphenyl)-2-(4-methylphenyl)-2,3-dihydro-4-pyri-
(d, J = 9.0 Hz, 2 H), 7.32–7.39 (m, 1 H), 6.98–7.18 (m, 5 H), 5.58
done (10b)
(d, J = 5.7 Hz, 1 H), 5.30 (d, J = 7.8 Hz, 1 H), 3.33–3.41 (m, 1 H),
2.70–2.76 (m, 1 H).
IR (KBr): 3851, 2923, 1710, 1650, 1585, 1568, 1513, 1454, 1409,
–
1
1
367, 1321, 1280, 1184, 1101, 924, 852, 815, 774, 730, 699 cm .
13
C NMR (75 MHz, MeOH-d ): d = 193.4, 170.0, 150.4, 148.7,
4
1
H NMR (300 MHz, MeOH-d ): d = 8.05 (d, J = 7.5 Hz, 1 H), 7.92
d, J = 9.0 Hz, 2 H), 7.10–7.17 (m, 6 H), 5.47 (d, J = 5.4 Hz, 1 H),
142.0, 132.4, 132.1, 132.0, 118.6, 115.9, 115.6, 114.5, 114.2, 104.2,
61.6, 43.9.
4
(
5
2
.26 (d, J = 7.8 Hz, 1 H), 3.33–3.40 (m, 1 H), 2.67–2.73 (m, 1 H),
.27 (s, 3 H).
+
HRMS (MALDI–DHB): m/z [M + H ] calcd for C H FNO :
1
8
15
3
3
12.1031; found: 312.1046.
1
3
C NMR (75 MHz, MeOH-d ): d = 193.9, 170.0, 150.6, 148.9,
4
1
2
38.9, 135.8, 132.3, 130.7, 128.6, 127.2, 118.7, 103.9, 62.0, 44.2,
1.1.
1-(4-Carboxyphenyl)-2-(4-chlorophenyl)-2,3-dihydro-4-pyri-
done (10g)
HRMS (MALDI–DHB): m/z calcd for C H NO [M + H+]:
IR (KBr): 2926, 1705, 1650, 1583, 1568, 1513, 1492, 1406, 1321,
1
9
18
3
–1
1
210, 1093, 1014, 925, 826, 773, 701 cm .
3
08.1281; found: 308.1285.
1
H NMR (300 MHz, MeOH-d ): d = 8.11–8.14 (m, 1 H), 7.97 (d,
4
1
-(4-Carboxyphenyl)-2-(3-methylphenyl)-2,3-dihydro-4-pyri-
J = 9.0 Hz, 2 H), 7.29–7.38 (m, 4 H), 7.20 (d, J = 8.7 Hz, 2 H), 5.60
done (10c)
(d, J = 5.4 Hz, 1 H), 5.29–5.32 (m, 1 H), 3.34–3.46 (m, 1 H), 2.70–
2.76 (m, 1 H).
IR (KBr): 2925, 1710, 1650, 1567, 1513, 1411, 1366, 1321, 1220,
–
1
1
184, 1102, 850, 773, 699 cm .
13
C NMR (75 MHz, MeOH-d ): d = 193.5, 150.4, 148.8, 137.8,
4
1
H NMR (300 MHz, MeOH-d ): d = 8.13 (d, J = 7.8 Hz, 1 H), 7.96
d, J = 9.0 Hz, 2 H), 7.19–7.25 (m, 3 H), 7.07–7.12 (m, 3 H), 5.54
d, J = 5.7 Hz, 1 H), 5.30 (d, J = 7.8 Hz, 1 H), 3.34–3.42 (m, 1 H),
134.8, 132.4, 130.5, 130.2, 129.1, 118.7, 104.2, 61.5, 44.0.
4
(
(
+
HRMS (MALDI–DHB): m/z [M + H ] calcd for C H ClNO :
1
8
15
3
3
28.0735; found: 328.0735.
2
.71–2.77 (m, 1 H), 2.31 (s, 3 H).
1
3
C NMR (75 MHz, MeOH-d ): d = 193.8, 169.5, 150.5, 149.1,
1-(4-Carboxyphenyl)-2-(3-chlorophenyl)-2,3-dihydro-4-pyri-
done (10h)
4
1
6
40.1, 138.9, 132.4, 130.4, 130.0, 129.7, 127.8, 124.3, 118.7, 104.1,
2.1, 44.2, 21.6.
IR (KBr): 2920, 1709, 1651, 1584, 1568, 1513, 1474, 1412, 1364,
–
1
HRMS (MALDI–DHB): m/z calcd for C H NO [M + H+]:
3
1321, 1283, 1205, 1182, 1101, 997, 851, 791, 772, 697, 616 cm .
1
9
18
3
1
08.1281; found: 308.1277.
H NMR (300 MHz, MeOH-d ): d = 8.10 (d, J = 8.1 Hz, 1 H), 7.91–
4
7
.98 (m, 2 H), 7.11–7.35 (m, 6 H), 5.57 (d, J = 6.0 Hz, 1 H), 5.30
1
-(4-Carboxyphenyl)-2-(4-methoxyphenyl)-2,3-dihydro-4-pyri-
(d, J = 7.8 Hz, 1 H), 3.34–3.41 (m, 1 H), 2.69–2.75 (m, 1 H).
done (10d)
13
C NMR (75 MHz, MeOH-d ): d = 193.3, 170.0, 150.4, 148.6,
4
IR (KBr): 2927, 2618, 2257, 1701, 1655, 1586, 1569, 1512, 1459,
1
1
41.5, 136.0, 132.4, 131.7, 129.2, 128.6, 127.4, 125.8, 118.6,
04.2, 61.6, 43.9.
1
7
1
411, 1370, 1284, 1253, 1222, 1182, 1100, 1027, 996, 827, 773,
08, 654 cm .
–1
+
HRMS (MALDI–DHB): m/z [M + H ] calcd for C H ClNO :
18 15
3
H NMR (300 MHz, MeOH-d ): d = 8.06 (d, J = 7.5 Hz, 1 H), 7.93
4
3
28.0735; found: 328.0737.
(
(
d, J = 8.7 Hz, 2 H), 7.18 (m, 4 H), 6.86 (d, J = 8.7 Hz, 2 H), 5.48
d, J = 5.1 Hz, 1 H), 5.27 (d, J = 7.8 Hz, 1 H), 3.74 (s, 3 H), 3.32 (m,
1
-(4-Carboxyphenyl)-2-(4-bromophenyl)-2,3-dihydro-4-pyri-
1
H), 2.67–2.73 (m, 1 H).
done (10i)
1
3
C NMR (75 MHz, DMSO-d ): d = 190.0, 167.2, 158.5, 147.1,
IR (KBr): 3065, 2924, 1652, 1581, 1567, 1511, 1488, 1455, 1401,
1364, 1322, 1283, 1220, 1100, 1074, 1010, 993, 970, 821, 784, 702,
659 cm .
6
1
4
46.8, 130.7, 129.4, 127.3, 116.6, 114.2, 103.3, 69.8, 59.0, 55.0,
3.3.
–
1
+
1
HRMS (FT–MS): m/z [M ] calcd for C H NO : 323.1152; found:
H NMR (300 MHz, MeOH-d ): d = 8.07–8.10 (m, 1 H), 7.94 (d,
1
9
18
4
4
3
23.1160.
J = 8.7 Hz, 2 H), 7.47–7.52 (m, 2 H), 7.24 (d, J = 8.1 Hz, 2 H), 7.14
(
d, J = 8.7 Hz, 2 H), 5.55 (d, J = 4.5 Hz, 1 H), 5.26–5.29 (m, 1 H),
1
-(4-Carboxyphenyl)-2-(3-methoxyphenyl)-2,3-dihydro-4-pyri-
3.33–3.46 (m, 1 H), 2.68–2.75 (m, 1 H).
done (10e)
13
C NMR (75 MHz, MeOH-d ): d = 193.4, 172.2, 151.0, 147.8,
4
IR (KBr): 3063, 2935, 2617, 1699, 1634, 1583, 1565, 1514, 1489,
1
38.4, 133.1, 132.1, 129.4, 122.7, 118.7, 103.6, 61.7, 43.9.
–
1
1
411, 1368, 1287, 1218, 1191, 1097, 1034, 977, 857, 773, 699 cm .
+
HRMS (MALDI–DHB): m/z [M + H ] calcd for C H BrNO :
1
18 15
3
H NMR (300 MHz, MeOH-d ): d = 8.12–8.14 (m, 1 H), 7.97 (d,
4
3
72.0230; found: 372.0240.
J = 9.0 Hz, 2 H), 7.21–7.29 (m, 3 H), 6.84–6.89 (m, 3 H), 5.55 (d,
J = 5.7 Hz, 1 H), 5.30 (d, J = 7.5 Hz, 1 H), 3.75 (s, 3 H), 3.34–3.42
1
-(4-Carboxyphenyl)-2-(3-bromophenyl)-2,3-dihydro-4-pyri-
(
m, 1 H), 2.72–2.78 (m, 1 H).
done (10j)
1
3
C NMR (75 MHz, MeOH-d ): d = 193.8, 161.7, 150.6, 149.0,
IR (KBr): 3050, 2910, 1700, 1652, 1582, 1568, 1513, 1473, 1409,
1363, 1320, 1283, 1219, 1205, 1101, 996, 933, 852, 786, 695 cm .
4
–
1
1
6
40.6, 132.3, 131.7, 131.3, 121.0, 119.3, 118.7, 114.1, 113.2, 104.0,
2.1, 55.8, 44.1.
1
H NMR (300 MHz, MeOH-d ): d = 8.11 (d, J = 7.8 Hz, 1 H), 7.96
4
+
HRMS (MALDI–DHB): m/z [M + H ] calcd for C H NO :
(d, J = 8.4 Hz, 2 H), 7.44–7.49 (m, 2 H), 7.16–7.29 (m, 4 H), 5.59
(d, J = 5.7 Hz, 1 H), 5.30 (d, J = 8.1 Hz, 1 H), 3.33–3.46 (m, 1 H),
1
9
18
4
3
24.1230; found: 324.1220.
2
.32–2.35 (m, 1 H).
Synthesis 2005, No. 7, 1061–1068 © Thieme Stuttgart · New York