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and MeOH (3Â15 mL). The resin was stirred in MeOH/
CH2Cl2 (1:1) for 1 h and washing with the same
sequence of solvents was repeated. Then resin 3 was
dried under reduced pressure.
3-(4-Ethoxyphenyl)-6,7,8-trimethoxy-2,4-quinazolinedione
(A2B7). Yield 7 mg (15%), mp 263–264 ꢀC, IR (NaCl,
cmÀ1): 3050 (w, multiple), 2361 (w), 1719 (m), 1656 (s),
1513 (m, doublet), 1415 (m), 1362 (m). 1H NMR
(CDCl3): d 8.27 (s, 1H), 7.33 (s, 1H), 7.21–7.14 (d, 2H),
7.04–6.99 (d, 2H), 4.12–4.03 (q, 2H), 1.46–1.41 (t, 3H),
MS (m/z, FAB): 373([M+H] +).
Resin 3 (1 mmol), PyBOP 1.6g (3.08 mmol), diverse
aromatic amines (3.48 mmol), DIEA 1.09 g (8.46mmol)
and DMF 10 mL were added in round bottom flask.
The reaction was continued at rt for 24 h with stirring.
After filtration, the resin was washed with MeOH
(3Â15 mL), CH2Cl2 (3 15 mL) MeOH:CH2Cl2 (1:1)
(3Â15 mL), and MeOH (3Â15 mL). The resin was stir-
red in MeOH/CH2Cl2 (1:1) for 1 h and washing with the
same sequence of solvents was repeated. Then the resin
5 was dried under reduced pressure.
3-(4-Methoxyphenyl)-6-hydroxy-2,4-quinazolinedione
(A3B2). Yield 16mg (36%), mp 233–234 ꢀC, IR (NaCl,
cmÀ1): 3421 (s, broad), 2361 (w), 1717 (w), 1649 (s),
1511 (w). 1H NMR(CDCl3/CD3OD): d 7.45–7.44 (d,
1H), 7.20–7.16(m, 3H), 7.04–7.01 (d, 3H). MS ( m/z,
FAB): 285([M+H]+).
3-(4-Hydroxyphenyl)-6-hydroxy-2,4-quinazolinedione
(A3B4). Yield 26mg (60%), mp over 300 ꢀC, IR (NaCl,
cmÀ1): 2360 (s, doublet), 1714 (m), 1654 (m), 1516 (m),
1465 (m). 1H NMR(CDCl3/CD3OD): d 7.44–7.43 (d,
1H), 7.22–7.17 (d, 1H), 7.11–7.06(m, 3H), 6.95–6.90 (m,
2H). MS (m/z, FAB): 271 ([M+H]+).
3-Phenyl-2,4-quinazolinedione (A1B1). Yield 20 mg
(42%), mp 282–283 ꢀ, IR (NaCl, cmÀ1): 3211 (w), 2349
(w), 1734 (m), 1649(s). H NMR (CDCl3/CD3OD): d
8.19–8.16(d, 1H), 7.75 (t, 1H), 7.61–7.56(m, 3H), 7.38–
7.27 (m, 4H). MS (m/z): 238 (M+).
1
3-(4-Methoxyphenyl)-2,4-quinazolinedione (A1B2). Yield
54 mg (100%), mp 299–300 ꢀC, IR (NaCl, cmÀ1): 2355
(m), 1728 (m), 1646 (s, multiple), 1514 (m, multiple),
1272 (m, doublet). H NMR (CDCl3/CD3OD): d 8.15–
8.11 (d, 1H), 7.63–7.60 (t, 1H), 7.27–7.11 (m, 4H), 7.05–
7.01 (m, 2H), 3.86(s, 3H). MS ( m/z): 268 (M+).
3 - (3 - hydroxyphenyl) - 6 - hydroxy - 2,4 - quinazolinedione
(A3B5). Yield 4 mg (9%), oil, 1H NMR(CDCl3/
CD3OD): d 7.45–7.44 (d, 1H), 7.33–7.30 (t, 1H), 7.23–
7.18 (d, 1H), 7.08–7.05 (d, 1H), 6.94–6.93 (d, 1H), 6.76–
6.71 (m, 2H). MS(m/z, FAB): 271 ([M+H] +).
1
3-(2-Hydroxyphenyl)-6-hydroxy-2,4-quinazolinedione
(A3B6). Yield 8 mg (19%), mp over 300 ꢀC, IR (NaCl,
cmÀ11): 3225 (w), 2372 (w), 1711 (m), 1658 (s), 1499 (m).
1H NMR (CDCl3/CD3OD): d 7.45–7.44 (d, 1H), 7.28–
7.25 (t, 1H), 7.21–7.08 (m, 3H), 7.01–6.94 (m, 2H). MS
(m/z, FAB): 271 ([M+H]+).
3-(4-Hydroxyphenyl)-2,4-quinazolinedione (A1B4). Yield
8 mg (80%), mp over 300 ꢀC, IR (NaCl, cmÀ1): 3211
(w), 2355 (w), 1727 (m), 1648 (s), 1270 (m). H NMR
(CDCl3/CD3OD): d 8.12–8.08 (d, 1H), 7.66–7.63 (t,
1H), 7.28–7.18 (q, 2H), 7.11–7.07 (d, 2H), 6.96–6.93 (d,
2H). MS (m/z): 254 (M+).
1
1-Methyl-3-phenyl-2,4-quinazolinedione (A4B1). Yield
12 mg (34%), mp 225–227 ꢀC, IR (NaCl, cmÀ1):
3067(w), 2363 (w), 1708 (s), 1671 (s, doublet), 1611 (m),
1488 (m). H NMR (CDCl3/CD3OD): d 8.26–8.258 (d,
1H), 7.75–7.74 (t, 1H), 7.53–7.45 (m, 3H), 7.33–7.26(m,
2H). MS (m/z, FAB): 253 ([M+H]+).
3-(4-Methoxyphenyl)-6,7,8-trimethoxy-2,4-quinazoline-
dione(A2B2). Yield 8 mg (17%), mp 297–300 ꢀC, IR
(NaCl, cmÀ1): 3046(w, multiple), 2355 (w), 1719 (m),
1
1
1654 (s), 1512 (m). H NMR (CDCl3/CD3OD): d 8.30
(s, 1H), 7.33 (s, 1H), 7.23–7.17 (d, 2H), 7.06–7.01 (d,
2H), 4.00 (s, 6H), 3.91 (s, 3H), 3.85 (s, 3H). MS (m/z,
FAB): 359([M+H]+).
1 - Methyl - 3 - (4 - methoxyphenyl) - 2,4 - quinazolinedione
(A4B2). Yield 12 mg (31%), mp 191–192 ꢀC, IR (NaCl,
cmÀ1): 2918 (w), 2362 (s, doublet), 1711 (m), 1660 (m),
1608 (m), 1484 (m), 1391 (m). 1H NMR (CDCl3): d
8.28–8.26(m, 1H), 8.25–7.68 (d, 1H), 7.33–7.26(m, 2H),
7.21–7.17 (d, 2H), 7.04–7.01 (d, 2H), 3.85 (s, 3H), 3.65
(s, 3H). MS(m/z, FAB): 283([M+H]+).
3-(4-Hydroxyphenyl)-6,7,8-trimethoxy-2,4-quinazoline-
dione (A2B4). Yield 10 mg (22%), mp over 300 ꢀC, IR
(NaCl, cmÀ1): 2349 (w), 1719 (m), 1651 (s), 1514 (m,
doublet), 1360 (m). 1H NMR (CDCl3/CD3OD): d
7.28 (s, 1H), 7.04–7.00 (d, 2H), 6.91–6.87 (d, 2H),
3.96(s, H6), 3.86(s, 3H). MS (
([M+H]+).
m/z, FAB): 345
1 - Methyl - 3 - (3 - methoxyphenyl) - 2,4 - quinazolinedione
(A4B3). Yield 11 mg (28%), mp 217–219 ꢀC, IR (NaCl,
cmÀ1): 2941 (w, multiple), 2361 (w), 1709 (s), 1671 (s),
1609 (s), 1409 (s), 1428 (m), 1390 (s). 1H NMR(CDCl3):
d 8.28–8.25 (d, 1H), 7.74 (t, 1H), 7.33–7.26(m, 2H),
7.02–7.01 (d, 1H), 6.88–6.80 (m, 2H), 3.82 (s, 3H), 3.65
(s, 3H). MS (m/z, FAB): 283 ([M+H]+).
3-(3-Hydroxyphenyl)-6,7,8-trimethoxy-2,4-quinazoline-
dione (A2B5). Yield 10 mg (22%), mp 293–294 ꢀC, H
NMR (CDCl3/CD3OD): d 7.30–7.27 (d, 1H), 7.16–7.13
(d, 1H), 7.02–6.94 (m, 2H), 4.01 (s, 6H), 3.91 (s, 3H).
MS (m/z, FAB): 345 ([M+H] +).
1
3-(2-Hydroxyphenyl)-6,7,8-trimethoxy-2,4-quinazoline-
dione (A2B6). Yield 12 mg (27%), mp 288–289 ꢀC, H
1 - Methyl - 3 - (3 - hydroxyphenyl) - 2,4 - quinazolinedione
(A4B5). Yield 9 mg (24%), mp 300–301 ꢀC, H NMR
1
1
NMR (CDCl3): d 8.21(1H), 7.54–7.43 (m, 3H), 7.34–
7.30 (m, 2H), 4.06–3.96 (d, 6H), 3.91–3.86 (s, 3H). MS
(m/z, FAB) : 345 ([M+H]+).
(CDCl3/CD3OD): d 8.23–8.20 (d, 1H), 7.82 (t, 1H),
7.44–7.31(m, 3H), 6.95–6.91 (d, 1H), 6.77–6.73 (m, 2H),
3.67 (s, 3H). MS (m/z, FAB): 269([M+H]+).