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M. Adib et al.
LETTER
Hz, 2 H, CH2), 7.37–7.60 (m, 10 H, 10 × CH), 7.66 (d,
J = 7.9 Hz, 1 H, CH), 7.95 (d, J = 7.6 Hz, 2 H, 2 × CH), 8.44
(d, J = 7.9 Hz, 1 H, CH). 13C NMR (125.8 MHz, CDCl3):
d = 33.9, 46.8, 120.1, 126.6, 126.7, 127.1, 127.3, 127.6,
127.9, 128.4, 128.7, 130.0, 134.1, 135.3, 138.3, 147.0,
156.5, 162.3.
A.; Bijanzadeh, H. R. Tetrahedron Lett. 2007, 48, 3217.
(j) Adib, M.; Sheibani, E.; Mostofi, M.; Ghanbary, K.;
Bijanzadeh, H. R. Tetrahedron 2006, 62, 3435. (k) Adib,
M.; Mahdavi, M.; Mahmoodi, N.; Pirelahi, H.; Bijanzadeh,
H. R. Synlett 2006, 1765.
(25) Adib, M.; Ansari, S.; Mohammadi, A.; Bijanzadeh, H. R.
Tetrahedron Lett. 2010, 51, 30.
2-(4-Chlorophenyl)-3-phenylquinazoline-4 (3H)-one (4j,
Table 1, Entry 10)
(26) (a) Kornblum, N.; Jones, W. J.; Anderson, G. J. J. Am.
Chem. Soc. 1959, 81, 4113. (b) Kornblum, N.; Powers, J.
W.; Anderson, G. J.; Jones, W. J.; Larson, H. O.; Levand, O.;
Weaver, W. M. J. Am. Chem. Soc. 1957, 79, 6562.
(c) Dave, P.; Byun, H. S.; Engel, R. Synth. Commun. 1986,
16, 1343.
(27) Typical Procedure for the Preparation of Compounds
4a–m, Exemplified with 4a (Table 1, Entry 1)
A mixture of benzyl chloride (0.126 g, 1 mmol) and K2CO3
(1.5 mmol) in DMSO (1 mL) was stirred for 4 h at 90 °C.
Then, isatoic anhydride (0.163 g, 1 mmol) and aniline (0.093
g, 1 mmol) were added to the reaction mixture and stirring
continued at 90 °C for 2 h. The reaction mixture was cooled
to r.t., H2O (3 mL) was added, and stirring was continued for
1 h at ambient temperature. The white precipitate was
filtered, washed with H2O (2 × 2 mL), dried, and then
recrystallized from of n-hexane–EtOAc (3:1) to give 4a as
white solid.
Yield 0.312 g (94%); white solid. 1H NMR (500.1 MHz,
CDCl3): d = 7.12–7.21 (m, 4 H, 4 × CH), 7.26–7.33 (m, 5 H,
5 × CH), 7.52 (d, J = 7.9 Hz, 1 H, CH), 7.79 (d, J = 8.3 Hz,
2 H, 2 × CH), 8.34 (d, J = 8.1 Hz, 1 H, CH). 13C NMR (125.8
MHz, CDCl3): d = 121.1, 127.1, 127.4, 127.8, 128.1, 128.7,
129.3, 129.5, 130.6, 133.7, 134.9, 135.6, 137.2, 147.1,
154.8, 162.6.
2-(4-Chlorophenyl)-3-(4-methoxybenzyl)quinazolin-4
(3H)-one (4k, Table 1, Entry 11)
Yield 0.361 g (96%); white solid. 1H NMR (500.1 MHz,
CDCl3): d = 3.79 (s, 3 H, CH3), 5.22 (s, 2 H, CH2), 6.77 (d,
J = 8.2 Hz, 2 H, 2 × CH), 6.82 (d, J = 8.4 Hz, 2 H, 2 × CH),
7.33 (d, J = 8.2 Hz, 2 H, 2 × CH), 7.43 (d, J = 8.4 Hz, 2 H, 2
× CH), 7.49–7.53 (m, 1 H, CH), 7.70–7.81 (m, 2 H, 2 × CH),
8.33 (d, J = 7.9 Hz, 1 H, CH). 13C NMR (125.8 MHz,
CDCl3): d = 48.7, 55.1, 113.6, 121.1, 127.0, 127.2, 127.6,
128.1, 128.4, 128.8, 129.3, 133.9, 134.4, 136.2, 147.5,
155.7, 158.2, 162.5.
2,3-Diphenylquinazolin-4 (3H)-one (4a, Table 1, Entry 1)
Yield 0.286 g (96%); white solid. 1H NMR (500.1 MHz,
CDCl3): d = 7.12–7.35 (m, 10 H, 10 × CH), 7.53 (d, J = 7.8
Hz, 1 H, CH), 7.80 (d, J = 7.5 Hz, 2 H, 2 × CH), 8.33 (d,
J = 8.0 Hz, 1 H, CH). 13C NMR (125.8 MHz, CDCl3):
d = 121.0, 127.4, 127.8, 128.0, 128.2, 128.5, 128.7, 129.4,
129.5, 129.6, 135.0, 135.9, 138.2, 147.7, 155.2, 162.5.
3-(4-Methoxyphenyl)-2-phenylquinazolin-4 (3H)-one
(4c, Table 1, Entry 3)
3-(4-Methylphenyl)-2-(4-nitrophenyl)quinazolin-4 (3H)-
one (4m, Table 1, Entry 13)
Yield 0.328 g (92%); pale yellow solid. 1H NMR (500.1
MHz, CDCl3): d = 2.29 (s, 3 H, CH3), 7.00 (d, J = 8.3 Hz, 2
H, 2 × CH), 7.17 (d, J = 8.3 Hz, 2 H, 2 × CH), 7.51–7.62 (m,
3 H, 3 × CH), 7.90 (d, J = 8.2 Hz, 2 H, 2 × CH), 8.12 (d,
J = 8.2 Hz, 2 H, 2 × CH), 8.34 (d, J = 7.9 Hz, 1 H, CH). 13
C
NMR (125.8 MHz, CDCl3): d = 22.3, 121.7, 123.4, 127.2,
127.7, 127.9, 128.7, 129.9, 130.2, 134.4, 134.8, 139.3,
141.6, 147.4, 147.6, 153.2, 161.6.
Yield 0.312 g (95%); white solid. 1H NMR (500.1 MHz,
CDCl3): d = 3.75 (s, 3 H, OCH3), 6.77 (d, J = 8.2 Hz, 2 H, 2
× CH), 6.99 (d, J = 8.2 Hz, 2 H, 2 × CH), 7.15–7.23 (m, 3 H,
3 × CH), 7.35 (d, J = 7.7 Hz, 2 H, 2 × CH), 7.47 (d, J = 7.8
Hz, 1 H, CH), 7.73–7.77 (m, 2 H, 2 × CH), 8.33 (d, J = 8.0
Hz, 1 H, CH). 13C NMR (125.8 MHz, CDCl3): d = 55.3,
114.4, 121.0, 127.1, 127.4, 128.2, 128.8, 129.2, 129.6,
130.3, 130.5, 135.2, 136.3, 147.7, 155.5, 159.8, 162.7.
3-(4-Methoxybenzyl)-2-phenylquinazolin-4 (3H)-one (4f,
Table 1, Entry 6)
(28) (a) Narasimhulu, M.; Mahesh, K. C.; Reddy, T. S.; Rajesh,
K.; Venkateswarlu, Y. Tetrahedron Lett. 2006, 47, 4381.
(b) Khosropour, A. R.; Mohammadpoor-Baltork, I.;
Ghorbankhani, H. Tetrahedron Lett. 2006, 47, 3561.
(c) Xue, S.; McKenna, J.; Shieh, W. C.; Repi, O. J. Org.
Chem. 2004, 69, 6474. (d) Kamal, A.; Reddy, K. S.; Prasad,
B. R.; Babu, A. H.; Ramana, A. V. Tetrahedron Lett. 2004,
45, 6517.
Yield 0.308 g (90%); white solid. 1H NMR (500.1 MHz,
CDCl3): d = 3.79 (s, 3 H, OCH3), 5.20 (s, 2 H, CH2), 6.75 (d,
J = 8.1 Hz, 2 H, 2 × CH), 6.84 (d, J = 8.1 Hz, 2 H, 2 × CH),
7.33–7.56 (m, 6 H, 6 × CH), 7.76 (d, J = 7.7 Hz, 2 H, 2 ×
CH), 8.35 (d, J = 7.9 Hz, 1 H, CH). 13C NMR (125.8 MHz,
CDCl3): d = 48.7, 55.0, 113.2, 121.0, 127.0, 127.1, 127.7,
127.9, 128.4, 128.5, 128.7, 129.9, 134.0, 135.2, 147.0,
156.5, 158.8, 162.7.
(29) Liu, J. F.; Lee, J.; Dalton, A. M.; Bi, G.; Yu, L.; Baldino, C.
M.; McElory, E.; Brown, M. Tetrahedron Lett. 2005, 46,
1241.
(30) Levy, P. R.; Stephen, H. J. Chem. Soc. 1956, 985.
(31) Kshirsagar, U. A.; Mhaske, S. B.; Argade, N. P. Tetrahedron
Lett. 2007, 48, 3243.
(32) Montazeri, N.; Rad-Moghadam, K. Phosphorus, Sulfur
Silicon Relat. Elem. 2004, 179, 2533.
2-Phenyl-3-phenylethylquinazolin-4 (3H)-one (4g, Table
1, Entry 7)
(33) Bhat, B. A.; Sahu, D. P. Synth. Commun. 2004, 34, 2169.
(34) Zheng, Z.; Alper, H. Org. Lett. 2008, 10, 829.
(35) Dabiri, M.; Salehi, P.; Khajavi, M. S.; Mohammadi, A. A.
Heterocycles 2004, 63, 1417.
Yield 0.300 g (92%); white solid. 1H NMR (500.1 MHz,
CDCl3): d = 3.41 (t, J = 7.7 Hz, 2 H, CH2), 4.68 (t, J = 7.7
Synlett 2012, 23, 85–88
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