March 2010
Calcd. for C14
Found: C, 65.43; H, 3.52; O, 6.25; N, 10.95.
SnCl ꢀ 2H O-Catalyzed One-Pot Synthesis of 4(3H)-Quinazolinones from
471
2
2
Anthranilic Acid, Ortho Esters, and Amines under Solvent Free Conditions
H
9
ON
2
Cl: C, 65.51; H, 3.53; O, 6.23; N, 10.91.
2006, 42, 1038; (e) Hu, Y. G.; Yang, S. J.; Ding, M. W. Phosphorus
Sulfur Silicon 2004, 179, 1933; (f) Bahadur, S.; Saxena, M. Arch
Pharm (Weinheim) 1983, 316, 964.
3
IR (KBr): 1713, 1587, 1443 cm
-(4-Bromophenyl)quinazolin-4(3H)-one (4i). White solid.
ꢂ1
1
[
3] (a) Ablondi, F.; Gordon, S.; Morton, J., II; Williams, J. H. J
.
H NMR (500 MHz,
Org Chem 1952, 17, 14; (b) Koepfli, J. B.; Mead, J. F.; Brockman, J.
A. J Am Chem Soc 1947, 69, 1837.
DMSO-d ): d 8.55 (s, 1H), 8.01 (d, J ¼ 7.7 Hz, 1H), 7.60 (t, J
6
¼
7.5 Hz, 1H), 7.46–7.44 (m, 4H), 7.18 (d, J ¼ 7.5 Hz, 2H).
Anal. Calcd. for C14 ON Br: C, 55.84; H, 3.01; O, 5.31; N,
.30. Found: C, 55.77; H, 3.01; O, 5.32; N, 9.33.
-(4-Carboxylphenyl)quinazolin-4(3H)-one (4m). White
[
4] Abdel-Jalil, R. J.; Voelter, W.; Saeed, M. Tetrahedron Lett
004, 45, 3475.
5] Xie, C.; Li, H. X.; Liu, M. G.; Ding, M. W. Chin Chem
Lett 2008, 19, 505.
H
9
2
2
9
[
3
ꢂ1
1
solid. IR (KBr): 1701, 1593, 1484 cm . H NMR (500 MHz,
[
6] Layeva, A. A.; Nosova, E. V.; Lipunova, G. N.;
DMSO-d ): d 10.49 (s, 1H), 8.34 (s, 1H), 7.92–7.88 (m, 3H),
6
Trashakhova, T. V.; Charushin, V. N. J Fluorine Chem 2007, 128, 748.
7
¼
.71 (t, J ¼ 8.5 Hz, 2H), 7.63 (d, J ¼ 5.5 Hz, 1H), 7.31 (d, J
[
7] Deetz, M. J.; Malerich, J. P.; Beatty, A. M.; Smith, B. D.
Tetrahedron Lett 2001, 42, 1851.
8] Liu, X. W.; Fu, H.; Jiang, Y. Y.; Zhao, Y. F. Angew Chem
Int Ed Engl 2009, 48, 348.
9] Yang, R. Y.; Kaplan, A. Tetrahedron Lett 2000, 41, 7005.
8.5 Hz, 1H), 6.56 (d, J ¼ 5.5 Hz, 1H). Anal. Calcd. for
10 3 2
C H O N : C, 67.67; H, 3.79; O, 18.03. Found: C, 67.76; H,
3
15
[
.78; O, 18.00.
-Benzylquinazolin-4(3H)-one (4n). White solid. IR (KBr):
3
678, 1621, 1459 cm
[
ꢂ1
1
1
8
7
.
H NMR (500 MHz, DMSO-d
6
): d
[
[
[
[
10] Lakhan, R.; Srivastava, M. J Chem Sci 1993, 105, 11.
11] Das, B.; Banerjee, J. Chem Lett 2004, 33, 960.
.52 (s, 1H), 8.00 (d, J ¼ 7.5 Hz, 1H), 7.54–7.47 (m, 2H),
.41–7.36 (m, 4H), 7.32 (t, J ¼ 6.8 Hz, 1H), 7.13 (t, J ¼ 7.0
12] Jiang, Z. D.; Chen, R. F. Synth Commun 2005, 35, 503.
13] Wang, L. M.; Xia, J. J.; Qin, F.; Qian, C. T.; Sun, J. Syn-
2
Hz, 1H), 4.61 (s, 2H). Anal. Calcd. for C15H12ON : C, 76.26;
H, 5.12; O, 6.77. Found: C, 76.35; H, 5.10; O, 6.74.
thesis 2003, 1241.
14] Khosropour,
Ghorbankhani, H. Tetrahedron Lett 2006, 47, 3561.
15] Narasimhulu, M.; Mahesh, K. C.; Reddy, T. S.; Rajesh, K.;
[
A.
R.;
Mohammadpoor-Baltork,
I.;
REFERENCES AND NOTES
[
[
[
1] Weddige, A. J Prakt Chem 1887, 36, 141.
2] (a) Takaya, Y.; Chiba, T.; Tanitsu, M.; Murata, K.; Kim, H.
Venkateswarlu, Y. Tetrahedron Lett 2006, 47, 4381.
[16] Ighilahriz, K.; Boutemeur, B.; Chami, F.; Rabia, C.; Hamdi,
M.; Hamdi, S. M. Molecules 2008, 13, 779.
[17] Chari, M. A.; Mukkanti, D. S. K. Catal Commun 2006, 7,
787.
S.; Wataya, Y.; Oshima, Y. Parasitol Int 1998, 47, 380; (b) Cao, S. L.;
Feng, Y. P.; Jiang, Y. Y.; Liu, S. Y.; Ding, G. Y.; Li, R. T. Bioorg
Med Chem Lett 2005, 15, 1915; (c) Kornet, M. J.; Varia, T.; Beaven,
W. J Heterocycl Chem 1983, 20, 1553; (d) Yadav, M. R.; Shirude, S.
T.; Parmar, A.; Balaraman, R.; Giridhar, R. Chem Heterocycl Compd
[18] Wang, M.; Song, Z. G.; Wan, X.; Zhao, S. Monatsh Chem
2009, 140, 1205.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet