274 JOURNAL OF CHEMICAL RESEARCH 2011
Scheme 5
15 M.A. Zolfigol, G. Chehardoli, E. Ghaemi, E. Madrakian, R. Zare,
T. Azadbakht, K. Niknam and S. Mallakpour, Monatsh. Chem., 2008, 139,
261.
16 M.A. Zolfigol, S.h. Mallakpour, A. Khazaiae, R.G. Vaghaie and M. Torabi,
Russ. J. Org. Chem., 2004, 40, 914.
17 M.A. Zolfigol, M. Bagherzadeh, S. Mallakpour, G. Chehardoli, E. Kolvari,
A. Ghorbani-Choghamarani and N. Koukabi, Catal. Commun., 2007, 8,
256.
18 M.A. Zolfigol, G. Chehardoli, F. Shirini, S.E. Mallakpour and
H. Nasr-Isfahani, Synth. Commun., 2001, 31, 1965.
19 M.A. Zolfigol, M. Bagherzadeh, G. Chehardoli, S.E. Mallakpour, Synth.
Commun., 2001, 31, 1149.
20 M.A. Zolfigol, M. Bagherzadeh, S.E. Mallakpour, G. Chehardoli,
A. Ghorbani-Choghamarani, N. Koukabi, M. Dehghanian and
M. Doroudgar, J. Mol. Catal. A: Chem 2007, 270, 219.
21 M.A. Zolfigol, G. Chehardoli, E. Ghaemi, E. Madrakian, R. Zare,
T. Azadbakht, K. Niknam and S. Mallakpour, Monatsh. Chem., 2008, 139,
261.
over calcium chloride to afford a white powder (8.13 g, 98% yield,
203–205 °C). 1H NMR: 7.74–6.90 (m, 20 H), 4.93(d, J = 25.7 Hz,
2H). 13C NMR: 135.2, 134. 99, 134.1, 134.30, 134.22, 134.09, 134.02,
131.36, 131.28, 130.26, 130.16, 130.07, 128.51, 127.12, 127.05,
117.99, 117.30, 29.89 (d, J = 193 Hz, C-P). IR (KBr): 3050, 2985,
1600, 1495, 1410, 1200-1400, 1120, 960, 750, 670, 610. cm–1. Anal.
Calcd for C25H22NO3P (415.1): C, 72.28; H, 5.34; N, 3.37; O, 11.55;
P, 7.46. Found: C, 72.50; H, 5.30; N, 3.37; O, 11.8%.
Triazolinediones(1a–i, 3a): A suspension of (1mmol), urazole,
AlCl3 (0.5mmol) and BTPPN (1mmol) were added to dichlorometh-
ane (10 mL) and the suspension was vigorously stirred for 30 min
(Table 2). The residue was washed with CH2Cl2 (2 × 10 cm3) and
filtered. The filtrate was dried over anhydrous Na2SO4, which was
filtered off after the appropriate time. Then the filtrate was passed
through a short pad of silica gel for removing any remaining of reagent
residue. Dichloromethane was removed by using a distillation appara-
tus and a water-bath (40–50 °C). A crystalline or powder solid is
obtained in good yields.
22 M.A. Zolfigol, M. Bagherzadeh and S.E. Mallakpour, Synth. Commun.,
1999, 29, 4061.
23 M.A. Zolfigol, M. Torabi and S.E. Mallakpour, Tetrahedron, 2001, 57,
8381.
24 M.A. Zolfigol, R. Ghorbani-Vaghei, S. Mallakpour, G. Chehardoli,
A. Ghorbani-Choghamarani and A. Hosain-Yazdi, Synthesis, 2006, 1631.
25 M.A. Zolfigol, S.E. Mallakpour, A. Khazaiae, R.G. Vaghaie and M. Torabi,
Russ. J. Org. Chem., 2004, 40. 914.
We thank Shahrekord University Research Councial for partial
support of this work.
Received 23 February 2011; accepted 4 April 2011
Paper 1100588 doi: 10.3184/174751911X13042666649151
Published online: 1 June 2011
26 M.A. Zolfigol, H. Nasr esfahani, S.E. Mallakpour and M. Safaiee, Synlett,
2005, 761.
27 B. Karami, S. Mallakpour and M. Farahi, Heteroatom Chem., 2008, 19,
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28 A. Ghorbani-Choghamarani, M. Hajjami, H. Goudarziafshar, M.
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29 S.E. Mallakpour and M.A. Zolfigol, Indian J. Chem., B., 1999, 38, 777.
30 H. Firouzabadi and Z. Mostavipoor, Bull. Chem. Soc. Jpn., 1983, 56, 914.
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33 A.R. Hajipour, S.E. Mallakpour and H.A. Samimi, Synlett 2001, 11, 1735.
34 A.R. Hajipour, S.E. Mallakpour and H.A. Samimi, J. Chem. Research (S),
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