´ ´ˇ ´ ´ ˇ
P. Skala, M. Machacek, M. Vejsova, L. Kubicova, J. Kunes, and K. Waisser
878
Vol 46
NMR (75 MHz, DMSO): d 55.4, 114.1, 114.5, 117.7, 118.0,
121.3, 122.7, 131.5, 149.8, 151.2, 156.1, 166.1.
2,4-Dihydroxy-N-phenylbenzamide (2a). IR (KBr): CO
1635 cmꢄ1
;
1H NMR (75 MHz, DMSO): d 6.34 (d, J ¼ 2.4
2,6-Dihydroxy-N-phenylbenzamide (4a). IR (KBr): CO
Hz, 1 H, H-3), 6.39 (dd, J ¼ 2.4 Hz, J ¼ 8.7 Hz, 1 H, H-5),
7.08–7.15 (m, 1 H, H-40), 7.31–7.39 (m, 2 H, H-30, H-50),
7.64–7.70 (m, 2 H, H-20, H-60), 7.90 (d, J ¼ 8.7 Hz, 1 H, H-
6), 10.15 (bs, 1 H, OH), 10.20 (bs, 1 H, OH), 12.28 (bs, 1 H,
NH); 13C NMR (75 MHz, DMSO): d 103.1, 107.7, 108.0,
121.4, 124.2, 128.9, 130.6, 138.4, 161.9, 162.8, 167.5.
1
1654 cmꢄ1; H NMR (300 MHz, DMSO): d 6.41 (d, J ¼ 8.4
Hz, 2 H, H-3, H-5), 7.10–7.15 (m, 1 H, H-40 7.19 (t, J ¼ 8.4
Hz, 1 H, H-4), 7.32–7.38 (m, 2 H, H-30, H-50), 7.61–7.65 (m,
2 H, H-20, H-60), 10.73 (bs, 1 H, NH), 12.24 (bs, 2 H, OH);
13C NMR (75 MHz, DMSO): d 104.3, 107.6, 121.2, 124.7,
129.2, 133.8, 13.7, 159.8, 168.3.
2,4-dihydroxy-N-(4-methylphenyl)benzamide (2b). IR (KBr):
1
CO 1636 cmꢄ1; H NMR (300 MHz, DMSO): d 2.27 (s, 3 H,
2,6-Dihydroxy-N-(4-methylphenyl)benzamide (4b). IR (KBr):
1
CO 1651 cmꢄ1; H NMR (300 MHz, DMSO): d 2.28 (s, 3 H,
CH3), 6.31 (d, J ¼ 2.1 Hz, 1 H, H-3), 6.36 (dd, J ¼ 2.1 Hz,
J ¼ 8.7 Hz, 1 H, H-5), 7.12–7.20 (m, 2 H, H-30 H-50) 7.51–
7.57 (m, 2 H, H-20, H-60), 7.88 (d, J ¼ 8.7 Hz, 1 H, H-6),
10.01 (bs, 1 H, NH), 10.17 (bs, 1 H, OH), 12.36 (bs, 1 H,
OH); 13C NMR (75 MHz, DMSO): d 20.7, 103.1, 107.6,
107.8, 121.5, 129.3, 130.4, 133.3, 135.8, 162.0, 162.7, 167.5.
N-(4-Chlorophenyl)-2,4-dihydroxybenzamide (2c). IR (KBr):
CH3), 6.43 (d, J ¼ 8.4 Hz, 2 H, H-3, H-5), 7.16–7.22 (m, 3 H,
H-4, H-30, H-50), 7.50–7.56 (m, 2 H, H-20, H-60), 10.69 (bs, 1 H,
NH), 12.34 (bs, 2 H, OH); 13C NMR (75 MHz, DMSO): d 20.7,
104.1, 107.6, 121.2, 129.5, 133.8, 133.9, 135.1, 159.9, 168.3.
N-(4-Chlorophenyl)-2,6-dihydroxybenzamide (4c). IR (KBr):
1
CO 1648 cmꢄ1; H NMR (300 MHz, DMSO): d 6.42 (d, J ¼
1
CO 1647 cmꢄ1; H NMR (300 MHz, DMSO): d 6.33 (d, J ¼
8.1 Hz, 2 H, H-3, H-5), 7.19 (t, J ¼ 8.1 Hz, 1 H, H-4), 7.39–
7.45 (m, 2 H, H-30, H-50), 7.66–7.72 (m, 2 H, H-20 H-60),
10.74 (bs, 1 H, NH), 11.97 (bs, 2 H, OH); 13C NMR (75 MHz,
DMSO): d 105.1, 107.5, 122.6, 128.2, 129.0, 133.7, 136.8,
159.5, 168.1.
2.1 Hz, 1 H, H-3), 6.38 (dd, J ¼ 2.1 Hz, J ¼ 8.8 Hz, 1 H, H-
5), 7.36–7.43 (m, 2 H, H-30 H-50), 7.69–7.75 (m, 2 H, H-20, H-
60), 7.87 (d, J ¼ 8.8 Hz, 1 H, H-6), 10.23 (bs, 2 H, OH), 12.14
(bs, 1 H, NH); 13C NMR (75 MHz, DMSO): d 103.0, 107.8,
108.0, 122.8, 127.8, 128.8, 130.7, 137.5, 161.7, 162.8, 167.5.
2,4-Dihydroxy-N-(4-methoxyphenyl)benzamide (2d). IR (KBr):
2,6-Dihydroxy-N-(4-methoxyphenyl)benzamide (4d). IR (KBr):
1
CO 1652 cmꢄ1; H NMR (300 MHz, DMSO): d 3.75 (s, 3 H,
1
CO 1640 cmꢄ1; H NMR (300 MHz, DMSO): d 3.74 (s, 3 H,
OCH3), 6.42 (d, J ¼ 8.1 Hz, 2 H, H-3, H-5), 6.90–6.97 (m, 2
H, H-30, H-50), 7.20 (t, J ¼ 8.1 Hz, 1 H, H-4), 7.52–7.58 (m, 2
H, H-20, H-60), 10.63 (bs, 1 H, NH), 12.40 (bs, 2 H, OH); 13C
NMR (75 MHz, DMSO): d 55.4, 103.8, 107.6, 114.2, 122.9,
130,5, 133.8, 156.4, 160.0, 168.1.
OCH3), 6.31 (d, J ¼ 2.4 Hz, 1 H, H-3), 6.37 (dd, J ¼ 2.4 Hz,
J ¼ 8.7 Hz, 1 H, H-5), 6.90–6.96 (m, 2 H, H-30, H-50), 7.52–
7.58 (m, 2 H, H-20, H-60), 7.89 (d, J ¼ 8.7 Hz, 1 H, H-6),
10.04 (bs, 1 H, OH), 10.17 (bs, 1 H, OH), 12.47 (bs, 1 H,
NH); 13C NMR (75 MHz, DMSO): d 55.4, 103.1, 107.5,
107.6, 114.0, 123.1, 130.1, 13102, 156.1, 162.3, 162.7, 167.6.
2,5-Dihydroxy-N-phenylbenzamide (3a). IR (KBr): CO
8-Hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione (5a).
1
IR (KBr): CO 1785, 1676 cmꢄ1; H NMR (300 MHz, DMSO):
d 7.24 (t, J ¼ 7.8 Hz, 1 H, H-6), 7.31 (dd, J ¼ 1.8 Hz, J ¼ 7.8
Hz, 1 H, H-7), 7.40 (dd, J ¼ 1.8 Hz, J ¼ 7.8 Hz, 1 H, H-5),
7.42–7.54 (m, 5 H, H-20, H-30, H-40, H-50, H-60), 10.54 (bs, 1 H,
OH); 13C NMR (75 MHz, DMSO): d 116.1, 116.9, 122.2, 125.4,
128.8, 129.2, 135.6, 141.7, 145.2, 147.7, 161.1.
1
1635 cmꢄ1; H NMR (300 MHz, DMSO): d 7.02 (d, J ¼ 8.7
Hz, 1 H, H-3), 7.10–7.17 (m, 1 H, H-40), 7.22 (dd,1 H, J ¼
2.7 Hz, J ¼ 8.7 Hz, H-4), 7.34-7.41 (m, 2 H, H-30, H-50),
7.67–7.74 (m, 3 H, H-6, H-20, H-60), 9.78 (bs, 1 H, OH), 10.40
(bs, 1 H, NH), 11.79 (bs, 1 H, OH); 13C NMR (75 MHz,
DMSO): d 118.1, 118.3, 121.0, 122.0, 124.5, 127.4, 129.0,
138.3, 142.6, 155.6, 169.7.
8-Hydroxy-3-(4-methylphenyl)-2H-1,3-benzoxazine-2,4(3H)-
dione (5b). IR (KBr): CO 1753, 1701 cmꢄ1 1H NMR (250
;
MHz, DMSO): d 2.37 (s, 3 H, CH3), 7.23 (t, J ¼ 7.5 Hz, 1 H,
H-6), 7.25–7.34 (m, 5 H, H-7, H-20, H-30, H-50, H-60), 7.39
(dd, J ¼ 1.8 Hz, J ¼ 7.5 Hz, 1 H, H-5), 10.49 (bs, 1 H, OH);
13C NMR (63 MHz, DMSO): d 20.5, 115.5, 116.5, 121.8,
124.9, 128.0, 129.2, 132.4, 137.9, 141.2, 144.7, 147.3, 160.7.
3-(4-Chlorophenyl)-8-hydroxy-2H-1,3-benzoxazine-2,4(3H)-
2,5-Dihydroxy-N-(4-methylphenyl)benzamide (3b). IR (KBr):
1
CO 1636 cmꢄ1; H NMR (300 MHz, DMSO): d 2.27 (s, 3 H,
CH3), 6.80 (d, J ¼ 8.7 Hz, 1 H, H-3), 6.87 (dd, J ¼ 3.0 Hz,
J ¼ 8.7 Hz, 1 H, H-4), 7.12–7.17 (m, 2 H, H-30, H-50), 7.36
(d, J ¼ 3.0 Hz, 1 H, H-6), 7.54–7.59 (m, 2 H, H-20, H-60),
9.10 (bs, 1 H, OH), 10.32 (bs, 1 H, NH), 11.10 (bs, 1 H, OH);
13C NMR (75 MHz, DMSO): d 20.7, 114.7, 118.0, 118.1,
120.9, 121.3, 129.4, 133.3, 136.0, 149.9, 150.9, 166.0.
;
dione (5c). IR (KBr): CO 1742, 1699 cmꢄ1 1H NMR
(300 MHz, DMSO): d 7.24 (t, J ¼ 7.8 Hz, 1 H, H-6), 7.30
(dd, J ¼ 1.8 Hz, J ¼ 7.8 Hz, 1 H, H-7), 7.39 (dd, J ¼ 1.8 Hz,
J ¼ 7.8 Hz, 1 H, H-5), 7.44–7.50 (m, 2 H, H-30, H-50), 7.54–
7.61 (m, 2 H, H-20, H-60), 10.55 (bs, 1 H, OH); 13C NMR (75
MHz, DMSO): d 116.0, 116.9, 122.3, 125.4, 129.3, 130.8,
133.5, 134.5, 141.6, 145.2, 147.6, 161.1.
N-(4-Chlorophenyl)-2,5-dihydroxybenzamide (3c). IR (KBr):
1
CO 1635 cmꢄ1; H NMR (300 MHz, DMSO): d 6.82 (d, J ¼
8.7 Hz, 1 H, H-3), 6.88 (dd, J ¼ 2.7 Hz, J ¼ 9.0 Hz, 1 H, H-
4), 7.33 (d, J ¼ 2.7 Hz, 1 H, H-6), 7.36–7.44 (m, 2 H, H-30,
H-50), 7.71–7.78 (m, 2 H, H-20 H-60), 9.14 (bs, 1 H, OH),
10.48 (bs, 1 H, NH), 10.95 (bs, 1 H, OH); 13C NMR (75 MHz,
DMSO): d 114.8, 118.1, 118.3, 121.4, 122.3, 127.8, 128.9,
137.6, 149.9, 150.6, 166.1.
8-Hydroxy-3-(4-methoxyphenyl)-2H-1,3-benzoxazine-2,4(3H)-
dione (5d). IR (KBr): CO 1766, 1704 cmꢄ1
;
1H NMR
(300 MHz, DMSO): d 3.81 (s, 3 H, OCH3), 7.00–7.07 (m, 2
H, H-30, H-50), 7.23 (t, J ¼ 7.8 Hz, 1 H, H-6), 7.27–7.36 (m, 3
H, H-7, H-20, H-60), 7.39 (dd, J ¼ 1.8 Hz, J ¼ 7.8 Hz, 1 H,
H-5), 10.48 (bs, 1 H, OH); 13C NMR (75 MHz, DMSO): d
55.6, 114.4, 116.1, 116.9, 122.1, 125.3, 128.0, 129.9, 141.6,
145.2, 147.9, 159.4, 161.3.
2,5-Dihydroxy-N-(4-methoxyphenyl)benzamide (3d). IR (KBr):
1
CO 1637 cmꢄ1; H NMR (300 MHz, DMSO): d 3.75 (s, 3 H,
OCH3), 6.81 (d, J ¼ 8.7 Hz, 1 H, H-3), 6.89 (dd, J ¼ 2.7 Hz,
J ¼ 8.7 Hz, 1 H, H-4), 6.91–6.96 (m, 2 H, H-30 H-50), 7.38 (d,
J ¼ 2.7 Hz, 1 H, H-6),7.56–7.62 (m, 2 H, H-20, H-60), 9.09
(bs, 1 H, OH), 10.28 (bs, 1 H, NH), 11.19 (bs, 1 H, OH); 13C
7-Hydroxy-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione (6a).
1
IR (KBr): CO 1770, 1699 cmꢄ1; H NMR (300 MHz, DMSO):
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet