Email this article 
Hide
Show all
OPEN ACCESS | 
PEER-REVIEWED |
RESEARCH ARTICLE
|
DOWNLOAD PDF
|
VIEW FULL-TEXT PDF
| TOTAL VIEWS
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.
Announcements
Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.
1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization or a DFT study between September 15, 2023 and October 31, 2023 (Voucher code: FALL2023).
2. A 50% discount will be applied to the article processing fee for submissions made between September 15, 2023 and October 31, 2023 by authors who have at least one publication in the European Journal of Chemistry (Voucher code: AUTHOR-3-2023).
3. Young writers will not be charged for the article processing fee between September 15, 2023 and October 31, 2023 (Voucher code: YOUNG2023).
Editor-in-Chief
European Journal of Chemistry
Keywords
Full Text:
PDF
DOI: 10.5155/eurjchem.1.4.291-293.108
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics
This Abstract was viewed 2247 times |
PDF Article downloaded 689 times
Citations
[1]. Pramod Kumar Sahu, Praveen Kumar Sahu, Raginee Jain, Ramjilal Yadav, Dau Dayal Agarwal
Hydrotalcite: recyclable, novel heterogeneous catalyst for facile, environmentally benign and high yielding multi-component synthesis and mechanistic study under solvent free conditions
Catalysis Science & Technology 2(12), 2465, 2012
DOI: 10.1039/c2cy20067h
[2]. Tentu Nageswara Rao, Nalla Krishnarao, Faheem Ahmed, Suliman Yousef Alomar, Fadwa Albalawi, Panagal Mani, Abdullah Aljaafari, Botsa Parvatamma, Nishat Arshi, Shalendra Kumar
One-Pot Synthesis of 7, 7-Dimethyl-4-Phenyl-2-Thioxo-2,3,4,6,7, 8-Hexahydro-1H-Quinazoline-5-OnesUsing Zinc Ferrite Nanocatalyst and Its Bio Evaluation
Catalysts 11(4), 431, 2021
DOI: 10.3390/catal11040431
[3]. Md. Afroz Bakht, Mshari. Alotaibi, Abdulrahman I. Alharthi, Israf Ud Din, Abuzer Ali, Amena Ali, Mohamed Jawed Ahsan
Pd-HPW/SiO2 Bi-Functional Catalyst: Sonochemical Synthesis, Characterization, and Effect on Octahydroquinazolinone Synthesis
Catalysts 11(11), 1273, 2021
DOI: 10.3390/catal11111273
[4]. Sajad Karami, Bahador Karami, Saeed Khodabakhshi
Solvent-free Synthesis of Novel and Known Octahydroquinazolinones/thiones by the Use of ZrOCl2.8H2O as a Highly Efficient and Reusable Catalyst
Journal of the Chinese Chemical Society 60(1), 22, 2013
DOI: 10.1002/jccs.201200145
[5]. Pramod K. Sahu, Praveen K. Sahu, Sushil K. Gupta, Dau D. Agarwal
Chitosan: An Efficient, Reusable, and Biodegradable Catalyst for Green Synthesis of Heterocycles
Industrial & Engineering Chemistry Research 53(6), 2085, 2014
DOI: 10.1021/ie402037d
[6]. Manisha R. Sawant, Suresh T. Gaikwad, Bhaskar H. Zaware, Anjali S. Rajbhoj
Synthesis of Dimethyl Octahydroquinazolinones by using Electrochemically Prepared Copper Oxide Nanoparticles
Asian Journal of Chemistry 32(8), 1895, 2020
DOI: 10.14233/ajchem.2020.22704
[7]. Sunita Jadhav, Priyanka L. Anandgaonker, Ganesh Kulkarni, Suresh T. Gaikwad, Anjali S. Rajbhoj
Microwave-Assisted One-Pot Synthesis of Octahydroquinazolinone Derivatives Using Molybdenum Oxide Nanoparticles in Solvent-Free Condition
Journal of Cluster Science 25(5), 1389, 2014
DOI: 10.1007/s10876-014-0716-2
[8]. Lipeeka Rout, Aniket Kumar, Pradyumna K Chand, L Satish K Achary, Priyabrat Dash
Microwave‐Assisted Efficient One‐Pot Multi‐Component Synthesis of Octahydroquinazolinone Derivatives Catalyzed by Cu@Ag Core‐Shell Nanoparticle
ChemistrySelect 4(19), 5696, 2019
DOI: 10.1002/slct.201900619
[9]. Aeysha Sultan, Abdul Raza, Muhammad Abbas, Khalid Khan, Muhammad Tahir, Nazamid Saari
Evaluation of Silica-H2SO4 as an Efficient Heterogeneous Catalyst for the Synthesis of Chalcones
Molecules 18(8), 10081, 2013
DOI: 10.3390/molecules180810081
[10]. Ali Dadashi Hadigavabar, Khalil Tabatabaeian, Mohammad Ali Zanjanchi, Manouchehr Mamaghani
Molybdenum anchored onto zeolite beta: an efficient catalyst for the one-pot synthesis of octahydroquinazolinone derivatives under solvent-free conditions
Reaction Kinetics, Mechanisms and Catalysis 124(2), 857, 2018
DOI: 10.1007/s11144-018-1370-8
[11]. Vahid Reza Hedayati, Mohammad Ali Ghasemzadeh
Efficient, One-Pot Synthesis of Polyfunctionalised Octahydroquinazolin-2,5-Diones Catalysed by Fe3O4 Nanoparticles
Journal of Chemical Research 39(1), 56, 2015
DOI: 10.3184/174751915X14199511243271
[12]. Asieh Yahyazadeh, Motahare Nafei-Kohi, Esmayeel Abbaspour-Gilandeh, Mehraneh Aghaei-Hashjin
A New Procedure for the Preparation of 3,4-dihydropyrimidin-2(1H)-one and Octahydroquinazolinone Derivatives catalyzed by SCMNPs@CA-EASO3H under Solvent-free Conditions
Letters in Organic Chemistry 19(10), 867, 2022
DOI: 10.2174/1570178619666211230123828
[13]. A. Kuraitheerthakumaran, S. Pazhamalai, H. Manikandan, M. Gopalakrishnan
Rapid and efficient one-pot synthesis of octahydroquinazolinone derivatives using lanthanum oxide under solvent-free condition
Journal of Saudi Chemical Society 18(6), 920, 2014
DOI: 10.1016/j.jscs.2011.11.014
[14]. Rajini Anumula, Muralasetti Nookaraju, Kaliaperumal Selvaraj, Ingala Ajit Kumar Reddy, Venkatathri Narayanan
A novel vanadium n-propylamino phosphate catalyst: synthesis, characterization and applications
Materials Research 16(1), 181, 2012
DOI: 10.1590/S1516-14392012005000161
[15]. S. L. Sangle, S. S. Ghumare
An Efficient Multicomponent Synthesis of Octahydroquinazolinone Derivatives Using Novel Recyclable Grafted Fe APA-Complex Catalyst
International Journal of Scientific Research in Science, Engineering and Technology , 30, 2018
DOI: 10.32628/IJSRSET11841110
[16]. Mohsen Abdel-Motaal Gomaa, Abdel-Wahed Rashad Sayed, Ragab Ali Masoud
One-pot multi-component synthesis of tetrahydroquinazolinones via Biginelli condensation using molecular iodine as a catalyst
European Journal of Chemistry 4(4), 459, 2013
DOI: 10.5155/eurjchem.4.4.459-461.821
[17]. Masoumeh Goudarzvand Chegini, Masoud Mokhtary
Polyvinylpolypyrrolidone-Supported Chlorosulfonic Acid: An Efficient Catalyst for One-Pot Synthesis of Dihydropyrimidinones and Octahydroquinazolin-2,5-diones
Polycyclic Aromatic Compounds 37(1), 63, 2017
DOI: 10.1080/10406638.2015.1088046
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
The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item
DOI Link: https://doi.org/10.5155/eurjchem.1.4.291-293.108
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
| 
Save to Zotero
Save to Mendeley
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
Refbacks
- There are currently no refbacks.
Copyright (c)
© Copyright 2010 - 2023 • Atlanta Publishing House LLC • All Right Reserved.
The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.
Copyright 2010-2023 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.