Synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles
References
[1] D. J. Sheehan, C. A. Hitchcock, C. M. Sibley, Clin. Microbiol. Rev. 1999, 12,
40.
[2] H. A. Barker, R. D. Smyth, H. Weissbach, J. I. Toohey, J. N. Ladd,
B. E. Volcani, J. Biol. Chem. 1960, 235, 480.
[3] Z. Kazimierczuk, J. A. Upcroft, P. Upcroft, A. Górska, B. Starooeciak,
A. Laudy, Acta Biochim. Pol. 2002, 49, 185.
[4] H. V. Huynh, J. H. H. Ho, T. C. Neo, L. L. Koh, J. Organometal. Chem. 2005,
690, 3854.
[5] G. L. Gravatt, B. C. Baguley, W. R. Wilson, W. A. Denny, J. Med. Chem.
1994, 37, 4338.
[6] M. M. Heravi, B. Baghernejad, H. A. Oskooie, Chin. J. Chem. 2009, 27,
379.
[7] T. Rott, M. L. Morningstar, P. L. Boyer, S. H. Hughes, R. W. Buckheit,
Scheme 2. Proposed mechanism for synthesis of 2-aryl-1-arylmethyl-1H-
1,3-benzimidazoles.
C. Michejda, J. Med. Chem. 1997, 40, 4199.
[8] K. J. Lee, K. D. Janda, Can. J. Chem. 2001, 79, 1556.
[9] I. Bhatnagar, M. V. George, Tetrahedron 1968, 24, 1293.
[10] H. Q. Ma, Y. L. Wang, J. P. Li, J. Y. Wang, Heterocycles 2007, 71, 135.
[11] P. L. Beaulieu, B. Hache, E. Von Moos, Synthesis 2003, 1683.
[12] L. H. Du, Y. G. Wang, Synthesis 2007, 675.
[13] M. Curini, F. Epifano, F. Montanari, O. Rosati, S. Taccone, Synlett 2004,
1832.
[14] P. Salehi, M. Dabiri, M. A. Zolfigol, S. Otokesh, M. Baghbanzadeh,
Tetrahedron Lett. 2006, 47, 2557.
[15] A. S. Zambare, J. N. Sangshetti, N. D. Kokare, D. B. Shinde, Chin. Chem.
Lett. 2009, 22, 171.
[16] R. Ghorbani-Vaghei, H. Veisi, Mol. Divers. 2010, 14, 249.
[17] H. Veisi, R. Ghorbani-Vaghei, A. Faraji, T. Ozturk, Chin. J. Chem. 2010, 28,
2249.
[18] H. Ahmadian, H. Veisi, C. Karami, A. Sedrpoushan, M. Nouri, F. Jamshidi,
I. Alavioon, Appl. Organometal. Chem. 2015, 29, 266.
[19] B. Maleki, D. Azarifar, S. F. Hojati, H. Veisi, M. Gholizadeh, H. Salehabadi,
M. Khodaverdian Moghadam, J. Heterocycl. Chem. 2011, 48, 449.
[20] H. Veisi, A. Sedrpoushan, M. A. Zolfigol, F. Mohanazadeh, J. Heterocycl.
Chem. 2011, 48, 1448.
[21] A. Khazaei, A. A. Manesh, Mendeleev Commun. 2006, 6, 109.
[22] A. Khazaei, A. Amini Manesh, J. Chin. Chem. Soc. 2005, 52, 1017.
[23] A. Khazaei, A. Amini Manesh, Synthesis 2005, 1929.
[24] A. Khazaei, A. Amini Manesh, A. Rostami, J. Chem. Res. 2005, 6, 391.
[25] A. Amini Manesh, F. Hosseini Eshbala, S. Hemmati, H. Veisi, RSC Adv.
2015, 5, 70265.
Table 4. Comparison of efficiency of various catalysts in synthesis of 2-
aryl-1-arylmethyl-1H-1,3-benzimidazoles
Entry
Catalyst
Conditions
Time Yield
Ref.
(min)
(%)
[14]
[32]
1
2
Silica sulfuric
acid
H2O, r.t.
120
70
Trifluoroacetic H2O–ethanol, r.t.
25
74
acid
[33]
[34]
3
4
SBA-Pr-SO3H
Acetic acid
Solvent-free, r.t.
Acetic acid–O2,
80 °C
25
25
88
92
[29]
[35]
5
6
K-10 clay
Solvent-free, MW
10
90
95
Amberlite IR- H2O–ethanol, r.t.
120
100
[36]
[31]
[37]
7
SiO2-Pr-SO3H Solvent-free, r.t.
60–120
120
20
90
90
72
8
Zn–proline
SiO2–ZnCl2
H2O, 25 °C
9
Solvent-free, MW
10
NH4Fe(SO4)2– Solvent-free, 70 °C
7
96 This work
H2O2
[26] H. Veisi, A. Amini Manesh, N. Khankhani, R. Ghorbani-Vaghei, RSC Adv.
2014, 4, 25057.
stated. 1H NMR spectra were recorded with a Bruker 200MHz NMR
spectrometer using tetramethysilane as internal standard and
chemical shifts (δ) were measured in ppm. Infrared spectra were
obtained using a PerkinElmer GX FT-IR spectrometer. All yields refer
to isolated products.
[27] A. Khazaei, A. Amini Manesh, J. Braz. Chem. Soc. 2005, 16, 874.
[28] S. Perumal, S. Mariappan, S. Selvaraj, Arkivoc 2004, 8, 46.
[29] S. B. Sapkal, K. F. Shelke, S. S. Sonar, B. B. Shingate, M. S. Shingare, Bull.
Catal. Soc. India 2009, 2, 78.
[30] M. Chakrabarty, S. Karmakar, A. Mukherji, S. Y. Arima, Y. Harigay,
Heterocycles 2006, 68, 967.
[31] V. Ravi, E. Ramu, K. Vijay, S. Rao, Chem. Pharm. Bull. 2007, 55, 1254.
[32] M. R. Mohammadizadeh, S. Z. Taghavi, Eur. J Chem. 2011, 8, 101.
[33] G. Mohammadi Ziarani, A. Badiei, M. Shakiba Nahad,
S. Ghadim Alizadeh, J. Nanostruct. 2012, 2, 213.
General procedure for synthesis of 2-aryl-1-arylmethyl-1H-1,3-
benzimidazoles
[34] D. Azarifar, M. Pirhayati, B. Maleki, M. Sanginabadi, R. N. Yami, J. Serb.
A mixture of o-phenylenediamine (1mmol), aryl aldehyde (2mmol)
and H2O2 (1mmol) was stirred with NH4Fe(SO4)2 (80 mg) at 70 °C for
a period of time specified in Table 1. The reaction was monitored
using TLC (n-hexane–acetone, 7:3). After completion of the reac-
tion, H2O (10 ml) was added, followed by extraction with CH2Cl2
(4× 10 ml) and drying over anhydrous MgSO4. Evaporation of the
solvent under reduced pressure gave the crude product which
was recrystallized from ethanol (90%).
Chem. Soc. 2010, 75, 1181.
[35] S. D. Sharma, D. Konwar, Synth. Commun. 2009, 39, 980.
[36] G. Mohammadi Ziarani, A. Badiei, M. Hassanzadeh, Int. J. Appl. Biol.
Pharm. Technol. 2011, 2, 48.
[37] R. G. Jacob, L. G. Dutra, C. S. Radatz, S. R. Mendes, G. Perin, E. J. Lenardao,
Tetrahedron Lett. 2009, 50, 1495.
Supporting Information
Additional supporting information may be found in the online ver-
Acknowledgements
sion of this article at the publisher’s web site
The authors acknowledge Payame Noor University Research Coun-
cils, Bu-Ali Sina University Research Councils, the Center of Excel-
lence in Development of Chemistry Methods (CEDCM) and
National Foundation of Elites (NFE) for support of this work.
Appl. Organometal. Chem. 2016, 30, 109–111
Copyright © 2015 John Wiley & Sons, Ltd.
wileyonlinelibrary.com/journal/aoc