European Journal of Chemistry

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



Main Article Content

Ghodsi Mohammadi Ziarani
Alireza Badiei
Monireh Shakiba Nahad
Malihe Hassanzadeh

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.

3_4_433_436_800


icon graph This Abstract was viewed 2424 times | icon graph Article PDF downloaded 908 times

How to Cite
(1)
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.

Article Details

Share
Crossref - Scopus - Google - European PMC
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

Supporting Agencies

Research Council of Alzahra University and University of Tehran, Iran
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).