G Model
CCLET 3458 1–6
6
G.R. Bardajee et al. / Chinese Chemical Letters xxx (2015) xxx–xxx
258
259
benzoxazoles and benzthiazoles under ambient conditions, J. Mol. Catal., A:
Chem. 214 (2004) 155–159.
[30] H. Goker, C. Ku, D.W. Boykin, S. Yildiz, N. Altanar, Synthesis of some new 2-
substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity
against Candida species, Bioorg. Med. Chem. 10 (2002) 2589–2596.
[31] K. Khosravi, S. Kazemi, Synthesis of 2-arylbenzimidazoles and 2-arylbenzothia-
zoles in both room temperature and microwave condition catalyzed by
hexamethylenetetramine–bromine complex, Chin. Chem. Lett. 23 (2012) 61–64.
[32] S.B. Sapkal, K.F. Shelke, S.S. Sonar, B.B. Shingate, M.S. Shingare, Acidic ionic liquid
catalyzed environmentally friendly synthesis of benzimidazole derivatives, Bull.
Catal. Soc. India 2 (2009) 78–83.
[33] D.V. Ramana, E. Kantharaj, Synthesis of 2-substituted benzoxazoles and benzi-
midazoles based on mass spectral ortho interactions, J. Chem. Soc., Perkin Trans. 2
(1995) 1497–1501.
[34] R.S. Pottorf, N.K. Chadha, M. Katkevics, et al., Parallel synthesis of benzoxazoles via
microwave-assisted dielectric heating, Tetrahedron Lett. 44 (2003) 175–178.
[35] R.S. Varma, R.K. Saini, O. Prakash, Hypervalent iodine oxidation of phenolic Schiff’s
bases: synthesis of 2-arylbenzoxazoles, Tetrahedron Lett. 38 (1997) 2621–2622.
[36] M.M. Heravi, N. Abdolhosseini, H.A. Oskooie, Re-gioselective and high-yielding
bromination of aromatic compounds using hexamethylenetetramine-bromine,
Tetrahedron Lett. 46 (2005) 8959–8963.
[37] S.V. Nalage, S.V. Bhosale, D.S. Bhosale, W.N. Jadhav, P2O5 mediated rapid conden-
sation of 2-aminothiophenol with aromatic aldehydes at ambient temperature,
Chin. Chem. Lett. 21 (2010) 790–793.
[38] Y. Li, Y.L. Wang, J.Y. Wang, A simple iodine-promoted synthesis of 2-substituted
benzothiazoles by condensation of aldehydes with 2-aminothiophenol, Chem.
Lett. 35 (2006) 460–461.
[39] M. Okimoto, T. Yoshida, M. Hoshi, et al., Electrooxidative cyclization of benzy-
lideneaminothiophenols to the corresponding 2-arylbenzothiazoles, Hetero-
cycles 75 (2008) 35–42.
[40] F.M. Masteri, F. Farzaneh, M. Ghandi, Synthesis and characterization of molybde-
num complexes with bidentate Schiff base ligands within nanoreactors of MCM-
41 as epoxidation catalysts, J. Mol. Catal., A: Chem. 248 (2006) 53–60.
[41] W.H. Zhang, X.B. Lu, J.H. Xiu, et al., Synthesis and characterization of bifunctio-
nalized ordered mesoporous materials, Adv. Funct. Mater. 14 (2004) 544–552.
[42] S. Jana, B. Dutta, R. Bera, S. Koner, Anchoring of copper complex in MCM-41
matrix: a highly efficient catalyst for epoxidation of olefins by tert-BuOOH,
Langmuir 23 (2007) 2492–2496.
[43] U.G. Singh, R.T. Williams, K.R. Hallam, G.C. Allen, Exploring the distribution of
copper–Schiff base complex covalently anchored onto the surface of mesoporous
MCM 41 silica, J. Solid State Chem. 178 (2005) 3405–3413.
[44] S. Singha, K.M. Parida, A.C. Dash, Fe(III)–salim anchored MCM-41: synthesis,
characterization and catalytic activity towards liquid phase cyclohexane oxida-
tion, J. Porous Mater. 18 (2011) 707–714.
300
301
302
303
304
305
306
307
308
309
310
311
312
313
314
315
316
317
318
319
320
321
322
323
324
325
326
327
328
329
330
331
332
333
334
335
336
337
338
339
340
341
260 Q4 [15] M. Terashima, M.A. Ishii, A facile synthesis of 2-substituted benzoxazoles, Syn-
261
262
263
264
265
266
267
268
269
270
271
272
273
274
275
276
277
278
279
280
281
282
283
284
285
286
287
288
289
290
291
292
293
294
295
296
297
298
299
thesis (1982) 484–485.
[16] A.K. Chakraborti, S. Rudrawar, G. Kaur, L. Sharma, An efficient conversion of
phenolic esters to benzothiazoles under mild and virtually neutral conditions,
Synlett 9 (2004) 1533–1536.
[17] Y. Pang, W. Hua, Efficient synthesis of 2-(20-hydroxyphenyl)benzoxazole by
palladium(II)-catalyzed oxidative cyclization, Tetrahedron Lett. 50 (2009)
6680–6683.
[18] W. Shen, T. Kohn, Z. Fu, et al., Synthesis of benzimidazoles from 1,1-dibro-
moethenes, Tetrahedron Lett. 49 (2008) 7284–7286.
[19] M.M. Heravi, S. Sadjadi, H.A. Oskoose, R.H. Shoar, Heteropoly acids as heteroge-
neous and recyclable catalysts for the synthesis of benzimidazoles, Catal. Com-
mun. 9 (2008) 504–507.
[20] R. Trivedi, S.K. De, R.A. Gibbs, A convenient one-pot synthesis of 2-substituted
benzimidazoles, J. Mol. Catal., A: Chem. 245 (2006) 8–11.
[21] G.R. Bardajee, R. Malakooti, I. Abtin, H. Atashin, Palladium Schiff-base complex
loaded SBA-15 as a novel nanocatalyst for the synthesis of 2,3-disubstituted
quinoxalines and pyridopyrazine derivatives, Microporous Mesoporous Mater.
169 (2013) 67–74.
[22] G.R. Bardajee, R. Malakooti, F. Jami, Z. Parsaei, H. Atashin, Covalent anchoring of
copper-Schiff base complex into SBA-15 as a heterogeneous catalyst for the
synthesis of pyridopyrazine and quinoxaline derivatives, Catal. Commun. 27
(2012) 49–53.
[23] M. Shakeri, R.J.M. Klein Gebbink, P.E. de Jongh, K.P. de Jong, Control and assess-
ment of plugging of mesopores in SBA-15 materials, Microporous Mesoporous
Mater. 170 (2013) 340–345.
[24] J. Liu, Y. Liu, W. Yang, et al., A novel and simple strategy for the direct synthesis
bimetallic mesoporous materials Zr–La-SBA-15, Mater. Lett. 128 (2014) 15–18.
[25] K.C. Gupta, A.K. Sutar, Catalytic activities of Schiff base transition metal com-
plexes, Coord. Chem. Rev. 252 (2008) 1420–1450.
[26] P.G. Cozzi, Metal–Salen Schiff base complexes in catalysis: practical aspects,
Chem. Soc. Rev. 33 (2004) 410–421.
[27] D. Zhao, J. Feng, Q. Huo, et al., Triblock copolymer syntheses of mesoporous silica
with periodic 50 to 300 angstrom pores, Science 279 (1998) 548–552.
[28] I.C. Chisem, J. Rafelt, M.T. Shieh, et al., Catalytic oxidation of alkyl aromatics
using a novel silica supported Schiff base complex, Chem. Commun. 18 (1998)
1949–1950.
[29] B.A. Abdelkrim, B. Khalid, S. Mohamed, Synthe`se chimiose´lective des benzimi-
dazoles sur silice traite´e par le chlorure du thionyle, Tetrahedron Lett. 44 (2003)
5935–5937.
Please cite this article in press as: G.R. Bardajee, et al., Simple and efficient protocol for the synthesis of benzoxazole, benzoimidazole
and benzothiazole heterocycles using Fe(III)–Schiff base/SBA-15 as a nanocatalyst, Chin. Chem. Lett. (2015), http://dx.doi.org/10.1016/