Evaluation Only. Created with Aspose.PDF. Copyright 2002-2021 Aspose Pty Ltd.
A. Davoodnia et al. / Chinese Chemical Letters 21 (2010) 550–553
553
1.2. Preparation of 2-arylquinazolin-4(3H)-ones 3a–g. General procedures
1.2.1. Method A
A mixture of 2-aminobenzamide (4 mmol), aromatic aldehyde (5 mmol) and TBAB (1.6 mmol) in the presence of
CuCl2 (1.4 mmol) was heated on the oil bath at 100 8C for 60–120 min. The progress of the reaction was monitored by
TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and then water was
added. The precipitate was filtered off and recrystallized from acetonitrile to give compounds 3a–g in high yields. All
products were known and characterized by 1H NMR and IR spectral data and comparision of their melting points with
those of authentic samples [8] (Table 2).
1.2.2. Method B
A mixture of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones 2a–g (1 mmol) and TBAB (0.4 mmol) in the presence of
CuCl2 (0.35 mmol) was heated on the oil bath at 100 8C for 60–90 min. The progress of the reaction was monitored by
TLC. After completion of the reaction, the reaction mixture was cooled to room temperature and then water was added.
The precipitate was filtered off and recrystallized from acetonitrile to give compounds 3a–g in high yields (Table 2).
1.2.3. Method C
A mixture of 2-aminobenzamide (4 mmol), aromatic aldehyde (5 mmol) and TBAB (1.6 mmol) was subjected to
microwave irradiation at 800 W and 120 8C for 2–4 min. After completion of the reaction (monitored by TLC), the
reaction mixture was cooled to room temperature and then water was added. The precipitate was filtered off and
recrystallized from acetonitrile to give compounds 3a–g in high yields (Table 2).
1
1.3. Selected H NMR data
2d: 1H NMR (DMSO-d6): d 2.31 (s, 3H, CH3), 5.72 (s, 1H, CH), 6.60–6.85 (m, 2H, arom-H), 7.06 (s, 1H, NH),
7.15–7.40 (m, 5H, arom-H), 7.62 (d, J = 7.6 Hz, 1H, arom-H), 8.26 (s, 1H, NH).
2e: 1H NMR (DMSO-d6): d 5.75 (s, 1H, CH), 6.60–6.95 (m, 2H, arom-H), 7.02 (s, 1H, NH), 7.10–7.85 (m, 6H,
arom-H), 8.22 (s, 1H, NH).
1
3d: H NMR (DMSO-d6): d 2.37 (s, 3H, CH3), 7.20–8.25 (m, 8H, arom-H), 12.27 (br, 1H, NH).
1
3e: H NMR (DMSO-d6): d 7.35–8.70 (m, 8H, arom-H), 12.15 (br, 1H, NH).
References
[1] A. Mannschreck, H. Koller, M.A. Davies, et al. Eur. J. Med. Chem. 19 (1984) 381.
[2] Y. Xia, Z. Yang, M. Hour, et al. Bioorg. Med. Chem. Lett. 11 (2001) 1193.
[3] M.S. Malamas, J. Miller, J. Med. Chem. 34 (1991) 1492.
[4] M. Hour, L. Huang, S. Kuo, et al. J. Med. Chem. 43 (2000) 4479.
[5] D.J. Connolly, D. Cusack, T.P. O’Sullivan, et al. Tetrahedron 61 (2005) 10153.
[6] J.X. Chen, H.Y. Wu, W.K. Su, Chin. Chem. Lett. 18 (2007) 536.
[7] J.J. Naleway, C.M.J. Fox, D. Robinhold, et al. Tetrahedron Lett. 35 (1994) 8569.
[8] M. Bakavoli, A. Shiri, Z. Ebrahimpour, et al. Chin. Chem. Lett. 19 (2007) 1403.
[9] R.J. Abdel-Jalil, W. Voelterb, M. Saeed, Tetrahedron Lett. 45 (2004) 3475.
[10] M. Bakavoli, O. Sabzevari, M. Rahimizadeh, Chin. Chem. Lett. 18 (2007) 1466.
[11] T.M. Potewar, R.N. Nadaf, T. Daniel, et al. Synth. Commun. 35 (2005) 231.
[12] J. Chen, D. Wu, F. He, et al. Tetrahedron Lett. 49 (2008) 3814.
[13] Sh. Rostamizadeh, A.M. Amini, R. Aryan, et al. Synth. Commun. 38 (2008) 3567.
[14] X.Y. Zhang, Y.Z. Li, X.S. Fan, et al. Chin. Chem. Lett. 17 (2006) 578.
[15] F.P. Yi, H.Y. Sun, M.H. Pan, et al. Chin. Chem. Lett. 20 (2009) 275.
[16] S. Kantevari, M.V. Chary, A.P.R. Das, et al. Catal. Commun. 9 (2008) 1575.
[17] M.V. Chary, N.C. Keerthysri, S.V.N. Vupallapati, et al. Catal. Commun. 9 (2008) 2013.
[18] A.R. Kiasat, R. Badri, S. Sayyahi, Chin. Chem. Lett. 19 (2008) 1301.
[19] A. Davoodnia, M. Bakavoli, Gh. Barakouhi, et al. Chin. Chem. Lett. 18 (2007) 1483.
[20] A. Davoodnia, M. Bakavoli, R. Moloudi, et al. Chin. Chem. Lett. 21 (2010) 1.
[21] A. Davoodnia, M. Rahimizadeh, Sh. Rivadeh, et al. Indian J. Heterocycl. Chem. 16 (2006) 151.
[22] A. Davoodnia, M. Roshani, E. Saleh Nadim, et al. Chin. Chem. Lett. 18 (2007) 1327.