Browse > Article
http://dx.doi.org/10.5012/bkcs.2013.34.11.3289

An Efficient and Environmentally Friendly Procedure for the Synthesis of Some Novel 8-Benzylidene-4-phenyl-3,4,5,6,7,8-hexahydro-1H-quinazolin-2-ones/thiones using Tetrabutylammonium Hexatungstate as a Reusable Heterogeneous Catalyst under Solvent-Free Conditions  

Ghashang, Majid (Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University)
Mansoor, Syed Sheik (Bioactive Organic Molecule Synthetic Unit, Research Department of Chemistry, C. Abdul Hakeem College)
Aswin, Krishnamoorthy (Bioactive Organic Molecule Synthetic Unit, Research Department of Chemistry, C. Abdul Hakeem College)
Publication Information
Abstract
An efficient method for the preparation of 8-benzylidene-4-phenyl-3,4,5,6,7,8-hexahydro-1H-quinazolin-2-ones/thiones from the reaction of aromatic aldehydes with cyclohexanone and urea or thiourea in the presence of Tetrabutylammonium hexatungstate, $[TBA]_2[W_6O_{19}]$, as an efficient, inexpensive catalyst under thermal and solvent-free conditions has been developed. Good yields, short reaction times, straightforward workup, reusability of the catalyst, and green conditions are the most obvious advantages of this procedure.
Keywords
Tetrabutylammonium hexatungstate; Benzylidene; Pyrimidinone; Quinazolin-2-ones; Quinazolin-2-thiones;
Citations & Related Records
Times Cited By KSCI : 3  (Citation Analysis)
연도 인용수 순위
1 Schreiber, S. L. Science 2000, 287, 1964.   DOI   ScienceOn
2 Burke, M. D.; Schreiber, S. L. Angew. Chem., Int. Ed. 2003, 43, 46.
3 Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898.   DOI
4 Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803.   DOI   ScienceOn
5 Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.   DOI   ScienceOn
6 Pandit, R. P.; Lee, Y. R. Bull. Korean Chem. Soc. 2012, 33, 3559.   DOI   ScienceOn
7 El-Subbagh, H. I.; Abu-Zaid, S. M.; Mahran, M. A.; Badria, F. A.; Al-Obaid, A. M. J. Med. Chem. 2000, 43, 2915.   DOI   ScienceOn
8 Ali, M. I.; El-Fotooh, A.; Hammam, G. J. Chem. Eng. Data 1978, 23, 351.   DOI
9 Ali, M. I.; El-Kaschef, M. A. F.; El-Fotooh, A.; Hammam, G.; Khallaf, S. A. J. Chem. Eng. Data 1979, 24, 377.   DOI
10 Ali, M. I.; El-Fotooh, A.; Hammam, G.; Youssef, N. M. J. Chem. Eng. Data 1981, 26, 214.   DOI
11 Biginelli, P. Gazz. Chim. Ital. 1893, 23, 360.
12 Kappe, C. O. Tetrahedron 1993, 49, 6937.   DOI   ScienceOn
13 Yarim, M.; Sarac, S.; Kilic, F. S.; Erol, K. Farmaco 2002, 58, 17.
14 Byk, G.; Gettlieb, H. E.; Herscovici, J.; Mirkin, F. J. Comb. Chem. 2000, 2, 732.   DOI   ScienceOn
15 Shaabani, A.; Bazgir, A.; Bijanzadeh, H. R. Mol. Diversity 2004, 8, 141.   DOI   ScienceOn
16 Elgemeie, G. E. H.; Attia, A. M. E.; Alkabai, S. S. Nucleos. Nucleot. Nucl. 2000, 19, 723.   DOI
17 Zhu, Y.; Huang, S.; Pan, Y. Eur. J. Org. Chem. 2005, 2354.
18 Zhang, H.; Zhou, Z.; Yao, Z.; Xu, F.; Shen, Q. Tetrahedron Lett. 2009, 50, 1622.   DOI   ScienceOn
19 Lei, M.; Ma, L.; Hu, L. Monatsh Chem. 2010, 141, 1005.   DOI
20 Hajipour, A. R.; Ghaye, Y.; Sheikhan, N.; Ruoho, A. E. Synth. Commun. 2011, 41, 2226.   DOI   ScienceOn
21 Davoodnia, A. Synth. React. Inorg. Met-Org. Nano-Met. Chem. 2012, 42, 1022.   DOI
22 Tavakoli-Hoseini, N. J. Chil. Chem. Soc. 2012, 57, 1432.   DOI
23 Mohammadzadeh-Dehsorkh, N.; Davoodnia, A.; Tavakoli-Hoseini, N.; Moghaddas, M. Synth. React. Inorg. Met-Org. Nano-Met. Chem. 2011, 41, 1135.   DOI
24 Davoodnia, A. Bull. Korean Chem. Soc. 2011, 32, 4286.   DOI   ScienceOn
25 Davoodnia, A.; Zare-Bidaki, A.; Behmadi, H. Chin. J. Catal. 2012, 33, 1797.   DOI
26 Davoodnia, A.; Khashi, M.; Tavakoli-Hoseini, N. Chin. J. Catal. 2013, 34, 1173.   DOI
27 Ashrafi, M.; Davoodnia, A.; Tavakoli-Hoseini, N. Bull. Korean Chem. Soc. 2013, 34, 1508.   DOI   ScienceOn
28 Ghashang, M.; Mansoor, S. S.; Aswin, K. J. Adv. Res. 2013, doi:10.1016/j.jare.2013.03.003
29 Ghashang, M.; Mansoor, S. S.; Aswin, K. Res. Chem. Intermed. 2013, doi: 10.1007/s11164-013-1027-1
30 Mansoor, S. S.; Aswin, K.; Logaiya, K.; Sudhan, S. P. N. Arab. J. Chem. 2012, http://dx.doi.org/10.1016/j.arabjc.2012.10.017
31 Mansoor, S. S.; Shafi, S. S.; Ahmed, S. Z. Arab. J. Chem. 2011, doi:10.1016/j.arabjc.2011.09.018
32 Mansoor, S. S.; Aswin, K.; Logaiya, K.; Sudhan, S. P. N. J. Saud Chem. Soc. 2012, http://dx.doi.org/10.1016/j.jscs.2012.07.011
33 Fournier, M. Inorg. Synth. 1990, 27, 80.