European Journal of Chemistry

One-pot multi-component synthesis of tetrahydroquinazolinones via Biginelli condensation using molecular iodine as a catalyst

Article Sidebar

PDF
Published: Dec 31, 2013
DOI: https://doi.org/10.5155/eurjchem.4.4.459-461.821
Keywords:
Urea, Dimedone, Biginelli reaction, Molecular iodine, Tetrahydroquinazolinone, Tetrahydroquinazolinthione
Section
Short Communication
Issue
Vol. 4 No. 4 (2013): December 2013
Dates
Received 2013-05-03
Accepted 2013-06-09
Published 2013-12-31


Main Article Content

Mohsen Abdel-Motaal Gomaa
Chemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt
Abdel-Wahed Rashad Sayed
Chemistry Department, Faculty of Science, Beni Suef University, 62511 Beni Suef, Egypt
Ragab Ali Masoud
College of Agriculture and Food Sciences, King Faisal University, Al-Hufuf 31982, Saudi Arabia

Abstract

Tetrahydroquinazolinone 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 molecular iodine 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.

4_4_459_461

icon graph This Abstract was viewed 2100 times | icon graph Article PDF downloaded 1204 times

How to Cite
(1)
Gomaa, M. A.-M.; Sayed, A.-W. R.; Masoud, R. A. One-Pot Multi-Component Synthesis of Tetrahydroquinazolinones via Biginelli Condensation Using Molecular Iodine As a Catalyst. Eur. J. Chem. 2013, 4, 459-461.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Niralwad, K. S.; Shingate, B. B.; Shingare, M. S. Tetrahedron Lett. 2010, 51, 3616-3618.
http://dx.doi.org/10.1016/j.tetlet.2010.04.118

[2]. Niralwad, K. S.; Shingate, B. B.; Shingare, M. S. J. Chin. Chem. Soc. 2010, 57, 89-92.

[3]. Bandgar, B. P.; More, P. E.; Kamble, V. T.; Totre, J. V. Arkivoc 2008, 15, 1-8.
http://dx.doi.org/10.3998/ark.5550190.0009.f01

[4]. Kidwai, M.; Saxena, S.; Khalilur, R. K.M.; Thukral, S. S. Eur. J. Med. Chem. 2005, 40, 816-819.
http://dx.doi.org/10.1016/j.ejmech.2005.02.009
PMid:16122583

[5]. Yarim, M.; Sarac, S.; Kilic, F. S.; Erol, K. Il Farmaco 2003, 58, 17-24.
http://dx.doi.org/10.1016/S0014-827X(02)00009-5

[6]. Yarim, M.; Sarac, S.; Ertan, M.; Kilic, F. S.; Erol, K. Arzneim. Forsch. 2002, 52, 27-33.
PMid:11838271

[7]. Eynde, J. J. V.; Godin, J.; Mayence, A.; Ma-questiau, A.; Anders, E. Synthesis 1993, 9, 867-869.
http://dx.doi.org/10.1055/s-1993-25958

[8]. Kempter, G.; Ehrlichmann, W.; Plesse, M.; Lehm, H. U. J. Prakt. Chem. 1982, 324, 832-840.
http://dx.doi.org/10.1002/prac.19823240518

[9]. Hassani, Z.;Islami, M. R.; Kalantari, M. Bioorg. Med. Chem. Lett. 2006, 16, 4479-4482.
http://dx.doi.org/10.1016/j.bmcl.2006.06.038
PMid:16806918

[10]. Mobinikhaledia, A.; Foroughifara, N.; Khodaeia, H. Eur. J. Chem. 2010, 1(4), 291-293.
http://dx.doi.org/10.5155/eurjchem.1.4.291-293.108

[11]. Debache, A.; Chouguiat, L.; Boulcina, R.; Carboni, B. The Open Org. Chem. J. 2012, 6, 12-20.

[12]. Walsh, P. J.; Li, H. M.; Parrodi, C. A. A. Chem. Rev. 2007, 107, 2503-2545.
http://dx.doi.org/10.1021/cr0509556
PMid:17530908 PMCid:PMC2525622

[13]. Saxena, I.; Borah, D. C.; Sarma, J. C. Tetrahedron Lett. 2005, 46, 1159-1160.
http://dx.doi.org/10.1016/j.tetlet.2004.12.081

[14]. Bhosale, R. S.; Bhosale, S. V.; Bhosale, S. V.; Wang, T.; Zubaidha, P. K. Tetrahedron Lett. 2004, 45, 9111-9113.
http://dx.doi.org/10.1016/j.tetlet.2004.10.021

[15]. Ko, S.; Sastry, M. N. V.; Lin, C.; Yao, C. F. Tetrahedron Lett. 2005, 46, 5771-5774.
http://dx.doi.org/10.1016/j.tetlet.2005.05.148

[16]. Srinivas, K. V. N. S.; Das, B. Synthesis 2004, 13, 2091-2093.

[17]. Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7243-7247.
http://dx.doi.org/10.1016/S0040-4039(98)01555-X

[18]. Banik, B. K.; Zegrocka, O.; Banik, I.; Hackfeld, L.; Becker, F. F. Tetrahedron Lett. 1999, 40, 6731-6737.
http://dx.doi.org/10.1016/S0040-4039(99)01395-7

[19]. Gomaa, M. A. M. E-J.Chem. 2011, 8(S1), S91-S96.

[20]. Kappe, C. O. Tetrahedron 1993, 49, 6937-6963.
http://dx.doi.org/10.1016/S0040-4020(01)87971-0

[21]. Kappe, C. O. Acc. Chem. Res. 2000, 33, 879-888.
http://dx.doi.org/10.1021/ar000048h
PMid:11123887

[22]. Kantevari, S.; Bantu, R.; Nagarapu, L. Arkivoc 2006, 16, 136-148.

[23]. Shahani, A.; Sarvary, A. Rayan, A. H. Lett. Org. Chem. 2007, 4, 68-71.

Supporting Agencies

King Faisal University, Al-Hufuf 31982, Saudi Arabia
Most read articles by the same author(s)

Most read articles by the same author(s)

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).