906
F. K. Behbahani et al.
6. Wiggins KM, Kerr RL, Zheng Chen Z, Bielawski CW (2010) J
Mater Chem 20:5709
Table 4 Reusability of the catalyst in the model reaction
Entry
Cycle
RCHO
Yield (%)
7. Tennyson AG, Rosen EL, Collins MS, Lynch VM, Bielawski CW
(2009) Inorg Chem 48:6924
1
2
3
4
Fresh
1st
4-Chlorobenzaldehyde
4-Chlorobenzaldehyde
4-Chlorobenzaldehyde
4-Chlorobenzaldehyde
92
92
89
87
8. Czarny A, Wilson WD, Boykin DW (1996) J Heterocycl Chem
33:1393
9. Tidwell RR, Geratz JD, Dann O, Volz G, Zeh D, Loewe H (1978)
J Med Chem 21:613
2nd
3rd
10. Fairley TA, Tidwell RR, Donkor I, Naiman NA, Ohemeng KA,
Lombardy RJ, Bentley JA, Cory M (1993) J Med Chem 36:1746
11. Tagawa Y, Yamagata K, Sumoto K (2008) Heterocycles 75:415
12. Bahrami K, Khodaei MM, Kavianinia I (2007) Synthesis 4:547
13. Du LH, Wang YG (2007) Synthesis 5:675
14. Das B, Holla H, Srinivas Y (2007) Tetrahedron Lett 48:61
15. Varala R, Nasreen A, Enugala R, Adapa SR (2007) Tetrahedron
Lett 48:69
16. Ma H, Wang Y, Li J, Wang J (2007) Heterocycles 71:135
17. Nagawade RR, Shinde DB (2007) Indian J Chem 46B:349
18. Ramachary DB, Reddy GB (2006) Org Biomol Chem 4:4463
19. Ma H, Wang Y, Wang J (2006) Heterocycles 68:1669
20. Lin S, Yang L (2005) Tetrahedron Lett 46:4315
21. Curini M, Epifano F, Montanari F, Rosati O, Taccone S (2004)
Synlett 10:1832
filtered, washed with n-hexane and subsequently dried. The
corresponding benzimidazole was obtained as the only
product (Table 3, Scheme 2). An identical procedure was
employed using o-phenylenediamine (2.0 mmol) and te-
rephthalaldehyde (1.0 mmol) stirred in 5 cm3 of 96%
EtOH in the presence of 0.030 g catalyst at room temper-
ature for 2 h for the synthesis of bis-benzimidazoles. All
the benzimidazoles produced were characterized in detail
by IR and 1H NMR spectroscopy and these data were
compared with those reported in the literature.
22. Itoh T, Nagata K, Ishikawa H, Ohsawa A (2004) Heterocycles
63:2769
23. Nagata K, Itoh T, Ishikawa H, Ohsawa A (2003) Heterocycles
61:93
Recyclability of the catalyst
The reusability of the catalyst was also studied. At the end
of the reaction, the catalyst was removed by filtration and
washed with diethyl ether. The recycled catalyst could be
subjected to further reactions. In the case of the model
reaction, after four runs the catalytic activity of catalyst
was almost the same as that of the freshly used catalyst
(Table 4).
24. Beaulieu PL, Hache B, Von Moos E (2003) Synthesis 11:1683
25. Chakrabarty M, Karmakar S, Mukherjee R, Arima S, Harigaya Y
(2009) Monatsh Chem 140:375
26. Rostamizadeh S, Amani AM, Aryan R, Ghaieni HR, Norouzi L
(2009) Monatsh Chem 140:547
27. Behbahani FK, Yektanezhad T, Korrami AR (2010) Heterocycles
81:2313
28. Heravi MM, Tajbakhsh M, Ahmadi AN, Mohajerani B (2006)
Monatsh Chem 137:175
29. Chakrabarty M, Mukherjee R, Karmakar S, Harigaya Y (2007)
Monatsh Chem 138:1279
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