LETTER
Oxidation of Urazoles with 1,3-Dihalo-5,5-dimethylhydantoin
763
Table 4 Oxidation of Urazoles 1 and Bis-urazoles 3 to their Corresponding Triazolinediones 2 and 4 with 1,3-Dibromo-5,5-dimethyl-
hydantoin (I) and 1,3-Dichloro-5,5-dimethylhydantoin (II) under Solvent-Free Conditions at Room Temperature
Urazole/bis-urazole Producta
Reagent/substrate (mmol)
Time (h)
Yield (%)b
Mp (°C)
Found
I
II
1
1
1
1
1
1
1
1
1
2
2
I (II)
Reported
98–98.53
537
1a
1b
1c
1d
1e
1f
2a8
1
1
1
1
1
1
1
1
1
2
2
2 (2)
2 (2)
–d (2)
2 (2)
2 (6)
2 (6)
2 (6)
2 (6)
2 (6)
–d (6)
4 (6)
100c (100)c
100c (100)c
–d (80)c
97–98
54–55
2b15
2c11,15
2d8
40–42
445
91 (80)c
86 (94)c
80 (96)c
77 (69)c
38 (65)c
71 (86)c
–d (56)c
42–43
44–44.53
95–963
2e8
95–97
2f8,10
2g8
171–175
132–135
125–126
111–113
145–150
170–1784
130–1323
128–1298
113–1156
146–1498
1g
1h
1i
2h8,15
2i12
3a
3b
4a15
4b15
33 (33)c
180–185 (dec.) 185 (dec.)8
a All of the isolated products are known compounds and their spectra and physical data have been reported in the literature.
b Isolated yields.
c Conversion.
d Reaction is very fast and explosive.
(10) Zolfigol, M. A.; Mallakpour, S. E.; Madrakian, E.; Ghaemi,
E. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.
2000, 39, 308.
(11) Zolfigol, M. A.; Chehardoli, G. A.; Mallakpour, S. E.; Nasr-
Isfahani, H. Synth. Commun. 2001, 31, 1965.
(12) Zolfigol, M. A.; Torabi, M.; Mallakpour, S. E. Tetrahedron
2001, 57, 8381; and other our references cited therein.
(13) Zolfigol, M. A.; Bagherzadeh, M.; Chehardoli, G. A.;
Mallakpour, S. E.; Mamaghani, M. J. Chem. Res., Synop.
2001, 390.
(14) Zolfigol, M. A.; Salehi, P.; Mallakpour, S. E.; Torabi, M.
Bull. Chem. Soc. Jpn. 2003, 76, 1673.
(15) Zolfigol, M. A.; Mallakpour, S. E.; Madrakian, E.; Ghaemi,
E. Synlett 2002, 1633.
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Soc. 2004, 25, 23.
(17) Azarifar, D.; Zolfigol, M. A.; Maleki, B. Synthesis 2004,
1744.
(18) Hilp, M. J. Pharm. Biomed. Anal. 2002, 28, 81.
(19) Hilp, M.; Senjuk, S. J. Pharm. Biomed. Anal. 2001, 25, 363.
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(22) Shimizu, M.; Nakahara, Y.; Yoshioka, H. J. Chem. Soc.,
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184.
Acknowledgment
Financial support for this work by the Research Council of Bu-Ali
Sina University, Hamadan, Iran, Isfahan University of Technology,
Isfahan, Iran, and Shahrood University of Technology, Shahrood,
Iran is gratefully acknowledged.
References
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