European Journal of Chemistry 2010, 1(4), 291-293 | doi: https://doi.org/10.5155/eurjchem.1.4.291-293.108 | Get rights and content

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Synthesis of octahydroquinazolinone derivatives using silica sulfuric acid as an efficient catalyst


Akbar Mobinikhaledi (1,*) , Naser Foroughifar (2) , Homila Khodaei (3)

(1) Department of Chemistry, Arak University, Arak, IR-38156-879, Iran
(2) Faculty of Chemistry, Islamic Azad University, North Tehran Branch, IR­1491367711, Iran
(3) Department of Chemistry, Arak University, Arak, IR-38156-879, Iran
(*) Corresponding Author

Received: 14 May 2010 | Revised: 04 Nov 2010 | Accepted: 14 Aug 2010 | Published: 22 Dec 2010 | Issue Date: December 2010

Abstract


Octahydroquinazolinone derivatives were synthesized in moderate to high yields via one-pot three component Biginelli reaction of dimedone, urea or thiourea and corresponding aromatic aldehydes in the presence of silica sulfuric acid as an efficient catalyst, in ethanol under reflux conditions. This protocol offers several advantages including good yields of products and easy experimental work-up procedure.

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Keywords


Quinazolinone; Silica sulfuric acid; Dimedone; Biginelli reaction

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DOI: 10.5155/eurjchem.1.4.291-293.108

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DOI: 10.1039/c2cy20067h
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[2]. Tentu Nageswara Rao, Nalla Krishnarao, Faheem Ahmed, Suliman Yousef Alomar, Fadwa Albalawi, Panagal Mani, Abdullah Aljaafari, Botsa Parvatamma, Nishat Arshi, Shalendra Kumar
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DOI: 10.3390/catal11040431
/


[3]. Sajad Karami, Bahador Karami, Saeed Khodabakhshi
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[4]. Pramod K. Sahu, Praveen K. Sahu, Sushil K. Gupta, Dau D. Agarwal
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[5]. Manisha R. Sawant, Suresh T. Gaikwad, Bhaskar H. Zaware, Anjali S. Rajbhoj
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DOI: 10.1590/S1516-14392012005000161
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DOI: 10.1080/10406638.2015.1088046
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References


[1]. Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043-1052.
doi:10.1016/S0223-5234(00)01189-2

[2]. Kung, P. -P.; Casper, M. D.; Cook, K. L.; Wilson-Lingardo, L.; Risen, L. M.; Vickers, T. A.; Ranken, R.; Blyn, L. B.; Wyatt, J. R.; Cook, P. D.; Ecker, D. J. J. Med. Chem. 1999, 42, 4705-4713.
doi:10.1021/jm9903500
PMid:10579832

[3]. Yarim, M.; Saraç, S.; Kiliç, F. S.; Erol, K. Il Farmaco 2003, 58, 17-24.
doi:10.1016/S0014-827X(02)00009-5

[4]. V Alagarsamy, V.; Pathak, U. S.; Sriram, D.; Pandeya, S. N.; Clercq E, De. Ind. J. Pharm. Sci. 2000, 62, 433-437.

[5]. Ladani, N. K.; Patel, M. P.; Patel, R. G, Arkivoc 2009, 7, 292-302.

[6]. Vanden Eynde, J. J.; Godin, J.; Mayence, A.; Maquestiau, A.; Anders, E. Synthesis 1993, 9, 867-869.
doi:10.1055/s-1993-25958

[7]. Kempter, G.; Ehrlichmann, W.; Plesse, M.; Lehm, H. -U. J. Pract. Chem. 1982, 324, 832-840.
doi:10.1002/prac.19823240518

[8]. Hassani, Z.; Islami, M. R.; Kalantari, M. Bioorg. Med. Chem. Lett. 2000, 16, 4479-4482.
doi:10.1016/j.bmcl.2006.06.038

[9]. Mobinikhaledi, A.; Foroughifar, N.; Karimi, G. Synth. React. Inorg. M. 2007, 37, 279-282.
doi:10.1080/15533170701316809

[10]. Zendehdel, M.; Mobinikhaledi. A.; Asgari, A. J. Incl. Phenom. Macro. 2008, 60, 353-357.
doi:10.1007/s10847-007-9384-2

[11]. Liu, C. -J.; Wang, J. -D. Molecules 2009, 14, 763-770.
doi:10.3390/molecules14020763
PMid:19223824

[12]. Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172-6183.
doi:10.1021/jo0342830
PMid:12895047

[13]. Tajbakhsh, M.; Mohajerani, B.; Heravi, M. M.; Ahmadi, A. N. J. Mol. Catal. A 2005, 236, 216-219.
doi:10.1016/j.molcata.2005.04.033

[14]. Zolfigol, M. A. Tetrahedron 2001, 57, 9509-9511.
doi:10.1016/S0040-4020(01)00960-7

[15]. Habibi, D.; Zolfigol, M. A.; Shiri, M.; Sedaghat, A. S. Afr. J. Chem. 2008, 61, 93-96.

[16]. Salehi, P.; Zolfigol, M. A.; Shirini, F.; Baghbanzadeh, M. Curr. Org. Chem. 2006, 10, 2171-2189.
doi:10.2174/138527206778742650

[17]. Habibi, D.; Zolfigol, M. A.; Shirini, F.; Safaiee, M.; Abedini, M.; Rahmani, P. S. Afr. J. Chem. 2007, 60, 17-19.

[18]. Bamoniri, A.; Zolfigoi, M. A.; Mohammadpoor-Baltork, I.; Mirjalili, B. F. J. Ir. Chem. Soc. 2006, 3, 85-88.

[19]. Foroughifar, N.; Mobinikhaledi, A.; Fathinajad, H. Phosphorus. Sulfur. 2003, 178, 1241-1246.
doi:10.1080/10426500307892

[20]. Mobinikhaledi, A.; Foroughifar, N.; Fathinajad, H. Phosphorus. Sulfur. 2004, 179, 2259-2263.
doi:10.1080/10426500490484751

[21]. Foroughifar, N.; Mobinikhaledi, A.; Shariatzadeh, S. M.; Masoudnia, M. Asian J. Chem. 2002, 14, 782-790.

[22]. Shaabani, A.; Sarvary, A.; Rahmati, A.; Rezayan, A. H. Lett. Org. Chem. 2007, 4, 68-71.
doi:10.2174/157017807780037531

[23]. Sabitha, G.; Reddy, K. B.; Yadav, J. S. Tetrahedron Let. 2003, 44, 6497-6499.
doi:10.1016/S0040-4039(03)01564-8


How to cite


Mobinikhaledi, A.; Foroughifar, N.; Khodaei, H. Eur. J. Chem. 2010, 1(4), 291-293. doi:10.5155/eurjchem.1.4.291-293.108
Mobinikhaledi, A.; Foroughifar, N.; Khodaei, H. Synthesis of octahydroquinazolinone derivatives using silica sulfuric acid as an efficient catalyst. Eur. J. Chem. 2010, 1(4), 291-293. doi:10.5155/eurjchem.1.4.291-293.108
Mobinikhaledi, A., Foroughifar, N., & Khodaei, H. (2010). Synthesis of octahydroquinazolinone derivatives using silica sulfuric acid as an efficient catalyst. European Journal of Chemistry, 1(4), 291-293. doi:10.5155/eurjchem.1.4.291-293.108
Mobinikhaledi, Akbar, Naser Foroughifar, & Homila Khodaei. "Synthesis of octahydroquinazolinone derivatives using silica sulfuric acid as an efficient catalyst." European Journal of Chemistry [Online], 1.4 (2010): 291-293. Web. 24 Sep. 2021
Mobinikhaledi, Akbar, Foroughifar, Naser, AND Khodaei, Homila. "Synthesis of octahydroquinazolinone derivatives using silica sulfuric acid as an efficient catalyst" European Journal of Chemistry [Online], Volume 1 Number 4 (22 December 2010)

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