G.-W. Wang et al.
Bull. Chem. Soc. Jpn. Vol. 79, No. 9 (2006) 1429
161.3; Anal. Calcd for C14H8Cl2N2O: C, 57.76; H, 2.77; N,
9.62%. Found: C, 57.59; H, 2.74; N, 9.54%; HRMS (+EI) calcd
for (Mþ): 290.0014, found: 290.0015.
1H, J ¼ 7:5 Hz, Ph), 7.69 (d, 1H, J ¼ 7:9 Hz, Ph), 7.82 (t, 1H,
J ¼ 7:6 Hz, Ph), 8.09 (d, 2H, J ¼ 8:7 Hz, Ph), 8.13 (d, 1H, J ¼
8:0 Hz, Ph), 10.22 (s, 1H, OH); 13C NMR (75 MHz, DMSO-d6):
ꢀ 115.4 (2C), 120.6, 123.2, 125.8, 125.9, 127.2, 129.6 (2C),
134.5, 149.1, 152.1, 160.6, 162.3; Anal. Calcd for C14H10N2O2:
C, 70.58; H, 4.23; N, 11.76%. Found: C, 70.46; H, 4.17; N,
11.85%; HRMS (+EI) calcd for (Mþ): 238.0742, found:
238.0750.
2-Styryl-4(3H)-quinazolinone (3o): IR (KBr) ꢃ 1669 (C=O),
1608, 1582, 1447, 1295, 1145, 968, 832, 767, 695 cmꢂ1; 1H NMR
(300 MHz, DMSO-d6) ꢀ 7.02 (d, 1H, J ¼ 16:2 Hz, Hvinyl), 7.40–
7.54 (m, 4H, Ph), 7.67–7.70 (m, 3H, Ph), 7.83 (t, 1H, J ¼ 7:7 Hz,
Ph), 7.98 (d, 1H, J ¼ 16:2 Hz, Hvinyl), 8.12 (d, 1H, J ¼ 7:8 Hz,
Ph); 13C NMR (75 MHz, DMSO-d6) ꢀ 121.1 (2C), 125.9, 126.2,
127.1, 127.6, 129.1 (2C), 129.8 (2C), 134.5, 135.0, 138.3, 149.0,
151.4, 161.7; Anal. Calcd for C16H12N2O: C, 77.40; H, 4.87; N,
11.28%. Found: C, 77.33; H, 4.92; N, 11.24%; HRMS (+EI) calcd
for (Mþ): 248.0950, found: 248.0943.
2-(4-Cyanophenyl)-4(3H)-quinazolinone (3d): IR (KBr) ꢃ
2225 (CꢅN), 1681 (C=O), 1603, 1558, 1468, 1311, 1151, 946,
843, 775, 554 cmꢂ1; 1H NMR (300 MHz, DMSO-d6) ꢀ 7.58 (t, 1H,
J ¼ 7:5 Hz, Ph), 7.79 (d, 1H, J ¼ 8:1 Hz, Ph), 7.88 (t, 1H, J ¼ 7:6
Hz, Ph), 8.05 (d, 2H, J ¼ 8:2 Hz, Ph), 8.18 (d, 1H, J ¼ 8:2 Hz,
Ph), 8.34 (d, 2H, J ¼ 8:2 Hz, Ph); 13C NMR (75 MHz, DMSO-
d6) ꢀ 113.5, 118.3, 121.1, 125.8, 127.2, 127.7, 128.6 (2C),
132.5 (2C), 134.7, 136.8, 148.3, 150.9, 162.0; Anal. Calcd for
C15H9N3O: C, 72.87; H, 3.67; N, 16.99%. Found: C, 72.95; H,
3.74; N, 16.86%; HRMS (+EI) calcd for (Mþ): 247.0746, found:
247.0752.
2-(4-Nitrophenyl)-4(3H)-quinazolinone (3f):
1682 (C=O), 1609, 1590, 1523, 1469, 1348, 1151, 1109, 946,
IR (KBr) ꢃ
1
859, 772, 707, 556 cmꢂ1; H NMR (300 MHz, DMSO-d6) ꢀ 7.59
(t, 1H, J ¼ 7:5 Hz, Ph), 7.80 (d, 1H, J ¼ 8:0 Hz, Ph), 7.89 (t, 1H,
J ¼ 7:6 Hz, Ph), 8.19 (d, 1H, J ¼ 8:1 Hz, Ph), 8.38 (d, 2H, J ¼
9:1 Hz, Ph), 8.43 (d, 2H, J ¼ 9:1 Hz, Ph); 13C NMR (75 MHz,
DMSO-d6) ꢀ 121.2, 123.6 (2C), 125.9, 127.3, 127.8, 129.3 (2C),
134.8, 138.6, 148.3, 149.0, 150.8, 162.1; Anal. Calcd for
C14H9N3O3: C, 62.92; H, 3.39; N, 15.72%. Found: C, 62.79; H,
3.57; N, 15.88%; HRMS (+EI) calcd for (Mþ): 267.0644, found:
267.0639.
2-(4-Furyl)-4(3H)-quinazolinone (3p):
(C=O), 1602, 1553, 1457, 1310, 965, 770, 753 cmꢂ1
IR (KBr) ꢃ 1663
1H NMR
;
(300 MHz, DMSO-d6) ꢀ 6.73 (dd, 1H, J ¼ 3:4, 1.3 Hz), 7.49 (t,
1H, J ¼ 7:5 Hz, Ph), 7.59 (d, 1H, J ¼ 3:4 Hz), 7.68 (d, 1H, J ¼
8:1 Hz, Ph), 7.81 (t, 1H, J ¼ 7:6 Hz, Ph), 7.97 (d, 1H, J ¼ 1:3 Hz),
8.11 (d, 1H, J ¼ 7:8 Hz, Ph); 13C NMR (75 MHz, DMSO-d6) ꢀ
112.5, 114.5, 121.1, 125.9, 126.4, 127.2, 134.6, 144.0, 146.1,
146.5, 148.6, 161.5; Anal. Calcd for C12H8N2O2: C, 67.92; H,
3.80; N, 13.20%. Found: C, 67.84; H, 3.78; N, 13.21%; HRMS
(+EI) calcd for (Mþ): 212.0586, found: 212.0592.
2-(2-Nitrophenyl)-4(3H)-quinazolinone (3g): IR (KBr) ꢃ
1664 (C=O), 1603, 1574, 1526, 1465, 1355, 1315, 1255, 1148,
;
943, 848, 776, 760, 716, 622, 543 cmꢂ1 1H NMR (300 MHz,
DMSO-d6) ꢀ 7.59 (t, 1H, J ¼ 7:5 Hz, Ph), 7.66 (d, 1H, J ¼ 8:1
Hz, Ph), 7.81–7.96 (m, 4H, Ph), 8.21 (t, 2H, J ¼ 9:1 Hz, Ph);
13C NMR (75 MHz, DMSO-d6) ꢀ 121.2, 124.5, 125.9, 127.1,
127.4, 129.2, 131.4, 131.5, 133.9, 134.7, 147.5, 148.5, 151.6,
161.5; Anal. Calcd for C14H9N3O3: C, 62.92; H, 3.39; N, 15.72%.
Found: C, 62.80; H, 3.46; N, 15.80%; HRMS (+EI) calcd for
(Mþ): 267.0644, found: 267.0641.
X-ray Crystallographic Data for 3j. C15H12N2O2, colorless,
crystal dimensions = 0:51 ꢄ 0:30 ꢄ 0:10 mm3, monoclinic, space
˚
group P21=n, a ¼ 10:4202ð14Þ, b ¼ 5:0199ð5Þ, c ¼ 22:802ð3Þ A,
ꢃ
3
˚
˚
ꢄ ¼ 98:102ð4Þ , V ¼ 1180:9ð3Þ A , Mr ¼ 252:27, Z ¼ 4, Dcalcd
¼
1:419 g cmꢂ3
,
ꢂ ¼ 0:71070 A,
ꢅ (Mo Kꢁ) = 0.096 mmꢂ1
,
Fð000Þ ¼ 880, S ¼ 1:156, R1 ¼ 0:0532, wR2 ¼ 0:1264. Crystallo-
graphic data for the structure reported have been deposited in the
Cambridge Crystallographic Data Centre (CCDC-249927). Crys-
tallographic data have been deposited with Cambridge Crystallo-
graphic Data Centre. Copies of the data can be obtained free of
from the Cambridge Crystallographic Data Centre, 12, Union
Road, Cambridge, CB2 1EZ, UK; Fax: +44 1223 336033; e-mail:
deposit@ccdc.cam.ac.uk).
2-(4-Hydroxyphenyl-3-methoxy)-4(3H)-quinazolinone (3k):
IR (KBr) ꢃ 1664 (C=O), 1578, 1527, 1483, 1288, 1248, 1120,
1027, 1018, 866, 769 cmꢂ1 1H NMR (300 MHz, DMSO-d6) ꢀ
;
3.90 (s, 3H, CH3), 6.93 (d, 1H, J ¼ 8:3 Hz, Ph), 7.49 (t, 1H, J ¼
7:4 Hz, Ph), 7.71 (d, 1H, J ¼ 8:0 Hz, Ph), 7.75 (d, 1H, J ¼ 8:3 Hz,
Ph), 7.82 (s, 1H, Ph), 7.85 (t, 1H, J ¼ 7:2 Hz, Ph), 8.13 (d, 1H,
J ¼ 7:8 Hz, Ph), 9.82 (s, 1H, OH); 13C NMR (75 MHz, DMSO-
d6) ꢀ 55.8, 111.3, 115.4, 120.6, 121.5, 123.4, 125.8, 125.9, 127.2,
134.5, 147.5, 149.0, 149.9, 162.3; Anal. Calcd for C15H12N2O3:
C, 67.16; H, 4.51; N, 10.44%. Found: C, 67.23; H, 4.65; N,
10.30%; HRMS (+EI) calcd for (Mþ): 268.0848, found:
268.0839.
We are grateful for the financial support from National Sci-
ence Fund for Distinguished Young Scholars (No. 20125205),
Anhui Provincial Bureau of Personnel Affairs (No. 2001Z019),
and Anhui Natural Science Foundation (No. 00045306).
2-(4-Dimethylaminophenyl)-4(3H)-quinazolinone (3l): IR
(KBr) ꢃ 1665 (C=O), 1607, 1590, 1535, 1487, 1370, 1292,
1
1208, 823, 768 cmꢂ1; H NMR (300 MHz, DMSO-d6) ꢀ 3.04 (s,
References
6H, 2 ꢄ CH3), 6.82 (d, 2H, J ¼ 9:0 Hz, Ph), 7.46 (t, 1H, J ¼
7:7 Hz, Ph), 7.68 (d, 1H, J ¼ 8:2 Hz, Ph), 7.81 (t, 1H, J ¼ 7:6 Hz,
Ph), 8.10 (d, 2H, J ¼ 9:0 Hz, Ph), 8.11 (d, 1H, J ¼ 8:0 Hz, Ph);
13C NMR (75 MHz, DMSO-d6) ꢀ 39.6, 111.3 (2C), 118.7, 120.3,
125.6, 125.8, 127.0, 128.9 (2C), 134.6, 145.3, 149.3, 152.3, 162.4;
Anal. Calcd for C16H15N3O: C, 72.43; H, 5.70; N, 15.84%. Found:
C, 72.57; H, 5.81; N, 15.73%; HRMS (+EI) calcd for (Mþ):
265.1215, found: 265.1218.
1
303.
2
J. H. Clark, D. J. Macquarrie, Chem. Soc. Rev. 1996, 25,
a) C.-J. Li, Chem. Rev. 1993, 93, 2023. b) A. Lubineau,
´
J. Auge, Top. Curr. Chem. 1999, 206, 1. c) C.-J. Li, Chem. Rev.
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3
L. M. Dudd, E. Venardou, E. Garcia-Verdugo, P. Licence,
A. J. Blake, C. Wilson, M. Poliakoff, Green Chem. 2003, 5, 187.
a) T.-S. Jin, A.-Q. Wang, X. Wang, J.-S. Zhang, T.-S. Li,
4
2-(4-Hydroxyphenyl)-4(3H)-quinazolinone (3n): IR (KBr) ꢃ
1668 (C=O), 1601, 1559, 1524, 1489, 1451, 1377, 1344, 1288,
Synlett 2004, 871. b) T.-S. Jin, J.-S. Zhang, J.-C. Xiao, A.-Q.
Wang, T.-S. Li, Synlett 2004, 866.
5 D. S. Bose, L. Fatima, H. B. Mereyala, J. Org. Chem.
2003, 68, 587.
1237, 1183, 948, 846, 765, 638, 612, 542, 526 cmꢂ1
;
1H NMR
(300 MHz, DMSO-d6) ꢀ 6.91 (d, 2H, J ¼ 8:7 Hz, Ph), 7.48 (t,