2-(1H)-PYRIDONES WITH ARYL DIAZO
1259
Ar-H), 8.1–8.2 (s, 2H, tr-H); 13C NMR (100 MHz, CDCl3) d: 50.1, 55.9, 85.0, 111.6,
112.4, 113.9, 114.3, 114.5, 117.3, 121.2, 126.9, 128.5, 128.9, 129.0, 129.8, 129.8, 130.2,
130.2, 131.0, 134.3, 135.1, 139.0, 145.8, 146.1, 151.0, 160.7; MS: m=z ¼ 516.09 (Mþ),
518.09 (Mþ þ 2), 520.09 (Mþ þ 4).
4-(4-Methoxyphenyl)-1-(3-chlorophenyl)-5-(3-chlorophenylazo)-6-(1H-
1,2,4-triazol-1-yl)-pyridin-2(1H)-one 17 (C26H18N6O2Cl2). IR (KBr): 1240 (C-O-
1
=
=
C), 1655 (>C O), 1560 (-N N-), 1425 (C-N), 3025 & 2910 (C-H str); H NMR
(400 MHz, CDCl3): 3.9–4.0 (q, 3H, OCH3), 6.6 (s, 1H, C3-H), 7.0–7.7 (m, 12H,
Ar-H), 8.1–8.2 (s, 2H, tr-H); 13C NMR (100 MHz, CDCl3) d: 50.1, 55.9, 85.0,
111.6, 112.4, 113.9, 114.3, 114.3, 117.3, 121.1, 126.9, 128.6, 128.9, 129.1, 129.8,
130.1, 130.2, 130.8, 134.3, 135.2, 139.1, 145.8, 146.2, 151.0, 160.7; MS: m=
z ¼ 516.09 (Mþ), 518.09 (Mþ þ 2), 520.09 (Mþ þ 4).
4-(4-Methoxyphenyl)-1-(3-chlorophenyl)-5-(4-chlorophenylazo)-6-(1H-
1,2,4-triazol-1-yl)-pyridin-2(1H)-one 18 (C26H18N6O2Cl2). IR (KBr): 3077 (Ar
=
C-H), 2979, 2925 (C-H), 1651 (C N), 1606 (C C), 1248 (C-O-C), 1712 (C O),
=
=
1
1572 (-N N-), 1511 (N-Ph); H NMR (400 MHz, CDCl3): 4.12 (s, 3H, OCH3),
=
6.67 (s, 1H, C3-H), 6.67–7.52 (m, 12H, Ar-H), 8.36 (s, 2H, C3-H & C5-H triaz);
13C NMR (100 MHz, CDCl3) d: 63.8, 89.7, 107.2, 114.2, 115.0, 115.4, 119.2, 120.6,
127.1, 127.8, 128.2, 129.1, 129.5, 131.9, 135.1, 137.4, 138.2, 141.3, 146.0, 151.3,
155.2, 160.9, 164.6; MS: m=z ¼ 516.09 (Mþ), 518.09 (Mþ þ 2), 520.09 (Mþ þ 4).
4-(4-Methoxyphenyl)-1-(3-chlorophenyl)-5-(2-methylphenylazo)-6-(1H-
1,2,4-triazol-1-yl)-pyridin-2(1H)-one 19 (C27H21N6O2Cl). IR (KBr): 1245 (C-O-
1
=
=
C), 1650 (>C O), 1575 (-N N-), 1445 (C-N), 3020 & 2920 (C-H str); H NMR
(400 MHz, CDCl3): 2.3 (s, 3H, CH3), 3.9–4.0 (q, 3H, OCH3), 6.6 (s, 1H, C3-H),
7.0–7.7 (m, 12H, Ar-H), 8.1–8.2 (s, 2H, tr-H); 13C NMR (100 MHz, CDCl3) d:
15.2, 50.1, 56.0, 85.0, 111.6, 112.4, 113.9, 114.3, 114.4, 117.3, 121.1, 125.8, 128.1,
128.5, 128.7, 128.7, 129.1, 129.8, 129.8, 131.3, 135.1, 137.1, 139.1, 145.8, 146.1,
151.2, 160.7; MS: m=z ¼ 496.14 (Mþ), 498.14 (Mþ þ 2).
4-(4-Methoxyphenyl)-1-(3-chlorophenyl)-5-(3-methylphenylazo)-6-(1H-
1,2,4-triazol-1-yl)-pyridin-2(1H)-one 20 (C27H21N6O2Cl). IR (KBr): 1265 (C-O-
1
=
=
C), 1665 (>C O), 1570(-N N-), 1430 (C-N), 3020 & 2910 (C-H str); H NMR
(400 MHz, CDCl3): 2.4 (s, 3H, CH3), 4.0–4.1 (q, 3H, OCH3), 6.6 (s, 1H, C3-H),
7.0–7.7 (m, 12H, Ar-H), 8.1–8.2 (s, 2H, tr-H); 13C NMR (100 MHz, CDCl3) d:
24.3, 50.1, 55.9, 85.0, 111.6, 112.4, 113.9, 114.3, 114.5, 117.3, 121.1, 125.8, 128.5,
128.6, 128.7, 129.1, 129.8, 129.8, 130.4, 131.0, 135.1, 138.4, 139.0, 145.8, 146.1,
151.2, 160.7; MS: m=z ¼ 496.14 (Mþ), 498.14 (Mþ þ 2).
4-(4-Methoxyphenyl)-1-(3-chlorophenyl)-5-(4-methylphenylazo)-6-(1H-
1,2,4-triazol-1-yl)-pyridin-2(1H)-one 21 (C27H21N6O2Cl). IR (KBr): 1255 (C-O-
1
=
=
C), 1660 (>C O), 1565 (-N N-), 1435 (C-N), 3020 & 2920 (C-H str), H NMR
(400 MHz, CDCl3): 2.3 (s, 3H, CH3), 3.9–4.1 (q, 3H, OCH3), 6.7 (s, 1H, C3-H),
7.0–7.7 (m, 12H, Ar-H), 8.1–8.2 (s, 2H, tr-H); 13C NMR (100 MHz, CDCl3) d:
24.3, 50.1, 55.9, 85.0, 111.6, 112.4, 113.9, 114.3, 114.3, 117.3, 121.1, 125.7, 128.5,
128.7, 128.7, 129.1, 129.1, 129.8, 129.8, 131.2, 135.1, 138.4, 139.0, 145.8, 146.0,
151.1, 160.7; MS: m=z ¼ 496.14 (Mþ), 498.14 (Mþ þ 2).