4
Tetrahedron Letters
A.; Karimi, N.; Mohammadizadeh, M. R.; Karimi, A. R.
slowly added with constantly stirring. The mixture was
refluxed for 2h, and then filtered. The obtained solid
was washed repeatedly with methanol until chlorine
could not be detected from its eluate, and calcined for
2h at 300℃to give the desired catalyst S1-S9.
Catal. Commun. 2006, 7, 752–755; (d) Mohammadpoor-
Baltork, I.; Mirkhani, V.; Moghadam, M.; Tangestaninejad, S.;
Zolfigol, M. A.; Abdollahi-Alibeik, M.; Khosropour, A. R.;
Kargar, H.; Hojati, S. F. Catal. Commun. 2008, 9, 894–901;
(e) Dabiri, M.; Salehi, P.; Baghbanzadeh, M.; Zolfigol, M. A.;
Agheb, M.; Heydari, S. Catal. Commun. 2008, 9, 785–788; (f)
Niknam, K.; Karami, B.; Zolfigol, M. A. Catal. Commun.
2007, 8, 1427–1430; (g) Zolfigol, M. A. Tetrahedron 2001,
57, 9509-9511; (h) Ghorbani-Choghamarani, A. ; Zolfigol, M.
A.; Rastegar, T. Chin. J. Catal. 2009, 30, 273-275; (i) Habibi,
D.; Zolfigol, M. A.; Safaiee, M.; Shamsian, A.; Ghorbani-
Choghamarani, A. Catal. Commun. 2009, 10, 1257-1260; (j)
Veisi, H. Tetrahedron Lett. 2010, 51, 2109-2114; (k) Shirini,
F.; Sadeghzadeh, P.; Abedini, M. Chin. Chem. Lett. 2009, 20,
1457-1460; (l) Zarei, A.; Hajipour, A. R.; Khazdooz, L.;
Mirjalili, B. F.; Chermahini, A. N. Dyes and Pigments, 2009,
81, 240-244; (m) Tamaddon, F.; Kargar-Shooroki, H.; Jafari,
A. A. J. Mol. Catal. A. 2013, 368–369, 66-71; (n) Rostamnia,
S.; Lamei, K. Chin. Chem. Lett. 2012, 23, 930-932; (o) Datta,
B.; Pasha, M. A. Chin. J. Catal. 2011, 32, 1180-1184; (p)
Ghorbani-Choghamarani, A.; Goudarziafshar, H.; Nikoorazm,
M.; Naseri, Z. Chin. Chem. Lett. 2011, 22, 1431-1434; (q)
Goudarziafshar, H. Chin. Chem. Lett. 2012, 23, 458-461; (r)
Modarresi-Alam, A. R.; Inaloo, I. D.; Kleinpeter, E. J. Mol.
Struct. 2012, 1024, 156-162; (s) Kiasat, A. R.; Davarpanah, J.
J. Mol. Catal. A. 2013, 373, 46-54; (t) Nikoorazm, M.
Scientia Iranica, 2013, 20, 603-606; (u) Zolfigol, M. A.;
Khazaei, A.; Mokhlesi, M.; Derakhshan-Panah, F. J. Mol.
Catal. A. 2013, 370, 111-116; (v) Du, L.; Yan, X.; He, G.;
Wu, X.; Hu, Z.; Wang, Y. Int. J. Hydrogen Energy, 2012, 37,
11853-11861.
10. Typical procedure for the synthesis of quinazolinone 3: o-
Aminobenzonitriles 1 (6 mmol), cycloketones 2 (6.1mmol),
and catalyst S1-S9 (0.5g) were added in water respectively
and refluxed with stirring for about 3h. After completion of
the reaction (indicated by TLC), the catalyst was filtered and
recovered, and the mixture was kept overnight. Then the
obtained residue was filtered and recrystallized with ethanol
to give the pure products 3.
1-Benzyl-spiro[piperidine-4,2'(1'H)-quinazolin]-4'(3'H)-one
1
(3d): light yellow solid. IR (KBr): 3326, 3180, 2924cm-1; H
NMR (400MHz, DMSO-d6) δ ppm: 1.78(2H, d, alkyl-H),
2.41-2.55 (4H, m, alkyl-H), 3.49 (2H, s, alkyl-H), 6.61 (1H, t,
J = 7.4Hz, ArH), 6.68 (1H, s, NH), 6.81(1H, d, J = 8.1Hz,
ArH), 7.22 (2H, dd, J = 7.5 Hz, J = 2.6 Hz, ArH), 7.27-7.33
(4H, m, J = 7.7 Hz, J = 2.0 Hz, ArH), 7.56 (1H, d, J = 7.7 Hz,
ArH), 7.96(1H, s, NH) ; 13C NMR (100 MHz, DMSO-d6) δ
ppm: 37.22 (2C), 48.63(2C), 62.22, 66.73, 115.0, 115.20,
117.17, 127.32, 127.60, 128.65(2C), 129.10(2C), 133.64,
139.23, 147.03, 163.68; MS (ESI): m/z (%) = 308.1 (100)
[M+H]+; Anal. Calcd for C19H21N3O: C 74.24, H 6.89, N
13.67; found C 74.04, H 6.96, N 13.47
7’-Chloro-spiro[cyclohexane-1,2'(1'H)-quinazolin]-4'(3'H)-
1
one (3i): white solid. IR (KBr): 3321, 3178, 2922cm-1; H
NMR (400MHz, DMSO-d6) δH: 1.25-1.77 (10H, m, C5H10),
6.62 (1H, dd, J = 8.0, 2.0 Hz, ArH), 6.87 (1H, d, J = 2.0 Hz,
ArH), 6.91 (1H, s, NH), 7.55 (1H, d, J = 8.0 Hz, ArH), 8.06
(1H, s, NH); 13C NMR (100 MHz, DMSO-d6) δC: 20.8 (2C),
24.5, 37.2 (2C), 68.1, 113.2, 113.6, 116.4, 129.1, 137.6, 147.7,
162.3.
9. Typical procedure for the preparation of catalysts S1-S9: Silica
sulfuric acid (2.5mmol H+/g) was prepared according to ref.
8(g). In a 250 ml suction flask equipped with a gas inlet tube
for conducting of HCl gas over an adsorbing solution (i.e.
water), 0.05mol metal chloride was dissolved in 50mL
anhydrous methanol. SSA (40g, 0.1mol sulfur content) was
11. CCDC-714116 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
from the Cambridge Crystallographic Data Centre, via