European Journal of Chemistry

Application of SBA-Pr-SO3H in the synthesis of benzoxazole derivatives

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Published: Dec 31, 2012
DOI: https://doi.org/10.5155/eurjchem.3.4.433-436.673
Keywords:
Benzoxazole, Nanoreactor, SBA-Pr-SO3H, 2-Aminophenol, Benzoyl chlorides, Hydroxy benzanilide
Section
Research Article
Issue
Vol. 3 No. 4 (2012): December 2012
Dates
Received 2012-08-19
Accepted 2012-09-01
Published 2012-12-31


Main Article Content

Ghodsi Mohammadi Ziarani
Department of Chemistry, Alzahra University, Vanak Square, Tehran, 199389-1176, Iran
Alireza Badiei
School of Chemistry, College of Science, University of Tehran, Tehran, 14155-6455, Iran
Monireh Shakiba Nahad
Department of Chemistry, Alzahra University, Vanak Square, Tehran, 199389-1176, Iran
Malihe Hassanzadeh
Department of Chemistry, Alzahra University, Vanak Square, Tehran, 199389-1176, Iran

Abstract

Propylsulfonic acid functionalized SBA-15 (SBA-Pr-SO3H) catalyzed the synthesis of 2-aryl benzoxazoles from 2-aminophenol and benzoyl chloride derivatives in good yields under reflux condition in acetic acid. In solvent free condition, hydroxybenzanilide derivatives were obtained.

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Ziarani, G. M.; Badiei, A.; Nahad, M. S.; Hassanzadeh, M. Application of SBA-Pr-SO3H in the Synthesis of Benzoxazole Derivatives. Eur. J. Chem. 2012, 3, 433-436.

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References

[1]. Kusumi, T.; Ooi, T.; Walchli, M. R.; Kakisawa, H. J. Am. Chem. Soc. 1988, 110, 2954-2958.
http://dx.doi.org/10.1021/ja00217a043

[2]. Chaney, M.; Demarco, P. V.; Jones, N. D.; Occolowitz, J. L. J. Am. Chem. Soc. 1974, 96, 1932-1933.
http://dx.doi.org/10.1021/ja00813a047

[3]. Haugwitz, R. D.; Maurer, B. V.; Jacobs, G. A.; Narayanan, V. L.; Cruthers, L.; Szanto, J. J. Med. Chem. 1979, 22, 1113-1118.
http://dx.doi.org/10.1021/jm00195a021

[4]. Dunwell, D. W.; Evans, D.; Hicks, T. A.; Cashin, C. H.; Kitchen, A. J. Med. Chem. 1975, 18, 53-58.
http://dx.doi.org/10.1021/jm00235a012

[5]. Dunwell, D. W.; Evans, D. J. Med. Chem. 1977, 20, 797-801.
http://dx.doi.org/10.1021/jm00216a011

[6]. Katsura, Y.; Nishino, S.; Inoue, Y.; Tomoi, M.; Takasugi, H. Chem. Pharm. Bull. 1992, 40, 371-380.
http://dx.doi.org/10.1248/cpb.40.371

[7]. McKee, M. L.; Kerwin, S. M. Bioorg. Med. Chem. 2008, 16, 1775-1783.
http://dx.doi.org/10.1016/j.bmc.2007.11.019
PMid:18037301 PMCid:2268758

[8]. Praveen, C.; Kumar, K. H.; Muralidharan, D.; Perumal, P. T. Tetrahedron 2008, 64, 2369-2374.
http://dx.doi.org/10.1016/j.tet.2008.01.004

[9]. Park, K. H.; Jun, K.; Shin, S. R.; Oh, S. W. Tetrahedron Lett. 1996, 37, 8869-8870.
http://dx.doi.org/10.1016/S0040-4039(96)02070-9

[10]. Chen, Y. X.; Qian, L. F.; Zhang, W.; Han, B. Angew. Chem. Int. Ed. 2008, 47, 9330-9333.
http://dx.doi.org/10.1002/anie.200803381
PMid:18972469

[11]. Wang, B.; Zhang, Y.; Li, P.; Wang, L. Chin. J. Chem. 2010, 28, 1697-1703.
http://dx.doi.org/10.1002/cjoc.201090287

[12]. Moghaddam, F. M.; Bardajee, G. R.; Ismaili, H.; Taimoory, S. M. D. Synth. Commun. 2006, 36, 2543-2548.
http://dx.doi.org/10.1080/00397910600781448

[13]. Naidu, A. B.; Sekar, G. Synthesis 2010, 579-586.

[14]. Johnson, S. M.; Connelly, S.; Wilson, I. A.; Kelly, J. W. J. Med. Chem. 2008, 51, 260-270.
http://dx.doi.org/10.1021/jm0708735
PMid:18095641

[15]. Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802-1808.
http://dx.doi.org/10.1021/jo051927q
PMid:16496964

[16]. Ueda, S.; Nagasawa, H. J. Org. Chem. 2009, 74, 4272-4277.
http://dx.doi.org/10.1021/jo900513z
PMid:19382756

[17]. Ueda, S.; Nagasawa, H. Angew. Chem. Int. Ed. 2008, 47, 6411-6413.
http://dx.doi.org/10.1002/anie.200801240
PMid:18618531

[18]. Bonnamour, J.; Bolm, C. Org. Lett. 2008, 10, 2665-2667.
http://dx.doi.org/10.1021/ol800744y
PMid:18507387

[19]. Reddy, M. B. M.; Nizam, A.; Pasha, M. A. Synth. Commun. 2011, 41, 1838-1842.
http://dx.doi.org/10.1080/00397911.2010.493260

[20]. Mosslemin, M. H.; Fazlinia, A. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 2165-2170.
http://dx.doi.org/10.1080/10426501003598630

[21]. Saha, P.; Ramana, T.; Purkait, N.; Ali, M. A.; Paul, R.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 8719-8725.
http://dx.doi.org/10.1021/jo901813g
PMid:19908912

[22]. Mohammadi Ziarani, G.; Badiei, A.; Aslani, Z.; Lashgari, N. Arab. J. Chem. 2012, In press, DOI: 10.1016/j.arabjc.2011.06.020
http://dx.doi.org/10.1016/j.arabjc.2011.06.020

[23]. Bahrami, K.; Khodaei, M. M.; Fattahpour, P. Catal. Sci. Technol. 2011, 1, 389-393.
http://dx.doi.org/10.1039/c1cy00053e

[24]. Ziarani, G. M.; Badiei, A. R.; Khaniania, Y.; Haddadpour, M. Iran. J. Chem. Chem. Eng. 2010, 29, 1-10.

[25]. Gholamzade, P.; Ziarani, G. M.; Badiei, A.; Bahrami, Z. Eur. J. Chem. 2012, 3(3), 279‐282.
http://dx.doi.org/10.5155/eurjchem.3.3.279-282.630

[26]. Lashgari, N.; Ziarani, G. M.; Badiei, A. R.; Gholamzade, P. Eur. J. Chem. 2012, 3(3), 310‐313.
http://dx.doi.org/10.5155/eurjchem.3.3.310-313.659

[27]. Wallnofer, P. R.; Safe, S.; Hutzinger, O. Pestic. Biochem. Physiol. 1971, 1, 458-463.
http://dx.doi.org/10.1016/0048-3575(71)90179-9

[28]. Sakurai, T.; Kojima, S.; Inoue, H. Bull. Chem. Soc. Jpn. 1990, 63, 3141-3148.
http://dx.doi.org/10.1246/bcsj.63.3141

[29]. Nagarajan, K.; Venkateswarlu, A.; Kulkarni, C. L.; Shah, R. K. Indian J. Chem. 1974, 12, 227-235.

[30]. Tingle, W. Amer. Chem. J. 1907, 37, 69-71.

[31]. Riadi, Y.; Mamouni, R.; Azzalou, R.; Haddad, M. E.; Routier, S.; Guillaumet, G.; Lazar, S. Tetrahedron Lett. 2011, 52, 3492-3495.
http://dx.doi.org/10.1016/j.tetlet.2011.04.121

[32]. Yang, F.; Wu, Y.; Zhu, Z.; Zhang, J.; Li, Y. Tetrahedron 2008, 64, 6782-6787.
http://dx.doi.org/10.1016/j.tet.2008.04.099

[33]. Keurulainen, L.; Salin, O.; Siiskonen, A.; Kern, J. M.; Alvesalo, J.; Kiuru, P.; Maass, M.; Yli-Kauhaluoma, J.; Vuorela, P. J. Med. Chem. 2010, 53, 7664-7674.
http://dx.doi.org/10.1021/jm1008083
PMid:20932010

[34]. Cadogan, J. I. G.; Husband, J. B.; McNab, H. J. Chem. Soc., Perkin Trans. 1 1984, 1449-1453.

[35]. Rtishchev, N.; Nosova, G.; Solovskaya, N.; Romashkova, K.; Kudryavtsev, V. Russ. J. Gen. Chem. 2005, 75, 1584-1593.
http://dx.doi.org/10.1007/s11176-005-0471-z

[36]. Rhijn, W. M. V.; Vos, D. E. D.; Sels, B. F.; Bossaert, W. D.; Jacobs, P. A. Chem. Commun. 1998, 317-318.
http://dx.doi.org/10.1039/a707462j

[37]. Lim, M. H.; Blanford, C. F.; Stein, A. Chem. Mater. 1998, 10, 467-470.
http://dx.doi.org/10.1021/cm970713p

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