

An efficient synthesis of quinoxalines catalyzed by monoammonium salt of 12-tungstophosphoric acid
Vijayalakshmi Kunkuma (1)





(1) Centre for Lipid Research, Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
(2) Centre for Lipid Research, Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
(3) Centre for Lipid Research, Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
(4) Centre for Lipid Research, Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
(5) Inorganic and Physical Chemistry Division, Indian Institute of Chemical Technology, Tarnaka, Hyderabad-500007, India
(*) Corresponding Author
Received: 28 Feb 2011 | Revised: 03 May 2011 | Accepted: 03 May 2011 | Published: 31 Dec 2011 | Issue Date: December 2011
Abstract
Monoammonium salt of 12-tungstophosphoric acid [(NH4)H2PW12O40] catalyst was used for the synthesis of biologically important quinoxaline derivatives in excellent yields from various aromatic 1,2-dicarbonyl and 1,2-diamines. The methodology has the advantages of mild reaction conditions with simple workup procedure, even for the synthesis of quinoxaline derivatives from sterically hindered diamine.
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.2.4.495-498.413
Links for Article
| | | | | | |
| | | | | | |
| | | |
Related Articles
Article Metrics


Funding information
Council of Scientific and Industrial Research (CSIR), India
Citations
[1]. M. Montana, F. Mathias, T. Terme, P. Vanelle
Antitumoral activity of quinoxaline derivatives: A systematic review
European Journal of Medicinal Chemistry 163, 136, 2019
DOI: 10.1016/j.ejmech.2018.11.059

[2]. Marc Montana, Vincent Montero, Omar Khoumeri, Patrice Vanelle
Quinoxaline Derivatives as Antiviral Agents: A Systematic Review
Molecules 25(12), 2784, 2020
DOI: 10.3390/molecules25122784

[3]. Debasish Bandyopadhyay, Jessica Cruz, Liza D Morales, Hadi D Arman, Erica Cuate, Young S Lee, Bimal K Banik, Dae J Kim
A green approach toward quinoxalines and bis-quinoxalines and their biological evaluation against A431, human skin cancer cell lines
Future Medicinal Chemistry 5(12), 1377, 2013
DOI: 10.4155/fmc.13.101

[4]. K. K. Durga Rao Viswanadham, Muktapuram Prathap Reddy, Pochampalli Sathyanarayana, Owk Ravi, Ruchir Kant, Surendar Reddy Bathula
Iodine-mediated oxidative annulation for one-pot synthesis of pyrazines and quinoxalines using a multipathway coupled domino strategy
Chem. Commun. 50(88), 13517, 2014
DOI: 10.1039/C4CC05844E

[5]. R. Nakache, T. Touil, A. El Hessni, A. Ouichou, Y. Bahbiti, I. Berkiks, M. Chakit, A. Mesfioui, Youcef Mehellou
In vivoacute toxicity assessment of a novel quinoxalinone (6-nitro-2 (1H)-quinoxalinone) in Wistar rats
Cogent Chemistry 3(1), 1301242, 2017
DOI: 10.1080/23312009.2017.1301242

[6]. Joana A. Pereira, Ana M. Pessoa, M. Natália D.S. Cordeiro, Rúben Fernandes, Cristina Prudêncio, João Paulo Noronha, Mónica Vieira
Quinoxaline, its derivatives and applications: A State of the Art review
European Journal of Medicinal Chemistry 97, 664, 2015
DOI: 10.1016/j.ejmech.2014.06.058

[7]. Mehdi Kalhor, Mahboubeh Shayestefar, Mehdi Khalaj, Fatemeh Janghorban
Ca(IO3)2 nanoparticles: fabrication and application as an eco-friendly and recyclable catalyst for the green synthesis of quinoxalines, pyridopyrazines, and 2,3-dicyano pyrazines
Research on Chemical Intermediates 49(3), 885, 2023
DOI: 10.1007/s11164-022-04914-3

[8]. R. K. Sharma, Shivani Sharma, Sriparna Dutta, Radek Zboril, Manoj B. Gawande
Silica-nanosphere-based organic–inorganic hybrid nanomaterials: synthesis, functionalization and applications in catalysis
Green Chemistry 17(6), 3207, 2015
DOI: 10.1039/C5GC00381D

[9]. Zahra Hashemi, Mohammad Ali Ebrahimzadeh, Pourya Biparva, Seyed Mohammad Abedirad
Pyridine-2-yl Quinoxaline (2-CPQ) Derivative As a Novel Pink Fluorophore: Synthesis, and Chemiluminescence Characteristics
Journal of Fluorescence 32(2), 723, 2022
DOI: 10.1007/s10895-022-02890-w

[10]. M. Esmaeilpour, A.R. Sardarian
Fe3O4@SiO2/Schiff base complex of metal ions as an efficient and recyclable nanocatalyst for the green synthesis of quinoxaline derivatives
Green Chemistry Letters and Reviews 7(3), 301, 2014
DOI: 10.1080/17518253.2014.948078

References
[1]. Shivaji, V. M.; Sastry, M. N. V.; Wang, C. C.; Ching-Fa Y. Tetrahedron Lett. 2005, 46, 6345-6348.
http://dx.doi.org/10.1016/j.tetlet.2005.07.026
[2]. Hui, X.; Desrivot, J.; Bories, C.; Loiseau P. M.; Franck, R.; Hocquemiller, R.; Figadere, B. Bioorg. Med. Chem. Lett. 2006, 16, 815-820.
http://dx.doi.org/10.1016/j.bmcl.2005.11.025
[3]. Sakata, G.; Makino, K.; Kurasama, Y. Heterocycles. 1988, 27, 2481-2515
http://dx.doi.org/10.3987/REV-88-397
[4]. Seitz, L. E.; Suling, W. J.; Reynolds, R. C. J. Med. Chem. 2002, 45, 5604-5606.
http://dx.doi.org/10.1021/jm020310n
PMid:12459027
[5]. Gazit, A.; App, H.; Mcmahon, G.; Chen, J.; Levitzki, A.; Böhmer, F. D. J. Med. Chem. 1996, 39, 2170-2177.
http://dx.doi.org/10.1021/jm950727b
PMid:8667360
[6]. Toshima, K.; Takano, R.; Ozawa, T.; Matsumura, S. Chem. Commun. 2002, 212-213.
http://dx.doi.org/10.1039/b107829c
PMid:12120371
[7]. Sonawane, N. D.; Rangnekar, D. W. J. Heterocycl. Chem. 2002, 39, 303-308.
http://dx.doi.org/10.1002/jhet.5570390210
[8]. Katoh, A.; Yoshida, T.; Ohkando, J. Heterocycles. 2000, 52, 911-920.
http://dx.doi.org/10.3987/COM-99-S61
[9]. Dailey, S.; Feast, J. W.; Peace, R. J.; Sage, I. C.; Till, S.; Wood, E. L. J. Mater. Chem. 2001, 11, 2238-2243.
http://dx.doi.org/10.1039/b104674h
[10]. oo, G. . H. C.; Snyder, J. K.; Wan, Z. K. Prog Heterocycl Chem, 2002, 14, 279-309.
[11]. Brown, D. J. Quinoxalines: Supplement II, in, The Chemistry of Heterocyclic Compounds, Taylor, E. C., Wipf, P. (Eds.). John Wiley & Sons, New Jersey, 2004.
[12]. Antoniotti, S.; Donach, E. Tetrahedron Lett. 2002, 43, 3971-3973.
http://dx.doi.org/10.1016/S0040-4039(02)00715-3
[13]. Robinson, R. S.; Taylor, R. J. K. Synlett. 2005, 6, 1003-1005.
[14]. Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Org. Biomol. Chem. 2004, 2, 788-796.
http://dx.doi.org/10.1039/b315689c
[15]. Raw, S. A.; Wilfred, C. D.; Taylor, R. J. K. Chem. Commun. 2003, 18, 2286-2287.
http://dx.doi.org/10.1039/b307177b
PMid:14518877
[16]. Venkatesh, C.; Singh, B.; Mahata, P. K.; Ha, H.; Junjappa, H. Org. Lett. 2005, 7, 2169-2172.
http://dx.doi.org/10.1021/ol0505095
PMid:15901161
[17]. Wu, Z.; Ede, N. J. Tetrahedron Lett. 2001, 42, 8115-8118.
http://dx.doi.org/10.1016/S0040-4039(01)01733-6
[18]. Xekoukoulotakis, N. P.; Hadjiantonious, M. C. P.; Maroulis, A. J. Tetrahedron Lett. 2000, 41, 10299-10302.
http://dx.doi.org/10.1016/S0040-4039(00)01847-5
[19]. Zhao, Z.; Wisnoski, D. D.; Wolkenberg, S. E.; Leister, W. H.; Wang, Y.; Lindsley, C. W. Tetrahedron Lett. 2004, 45, 4873-4876.
http://dx.doi.org/10.1016/j.tetlet.2004.04.144
[20]. Bhosale, R. S.; Sarda, S. R.; Ardhapure, S. S.; Jadhav, W. N.; Bhusare, S. R.; Pawar, R. P. Tetrahedron Lett. 2005, 46, 7183-7186.
http://dx.doi.org/10.1016/j.tetlet.2005.08.080
[21]. Heravi, M. M.; Taheri, S.; Bakhtiari, K.; Oskooie, H. A. Catal. Commun. 2007, 8, 211-214.
http://dx.doi.org/10.1016/j.catcom.2006.06.013
[22]. Heravi, M. M.; Tehrani, M. H.; Bakhtiari, K.; Oskooie, H. A. Catal. Commun. 2007, 8, 1341-1344.
http://dx.doi.org/10.1016/j.catcom.2006.11.026
[23]. Srinivas, C.; Kumar, C. N. S. S. P.; Jayathirtha Rao, V.; Palaniappan, S. J. Mol. Catal. A: Chem. 2007, 265, 227-230.
http://dx.doi.org/10.1016/j.molcata.2006.10.018
[24]. Dong, F.; Kai, G.; Zhenghao, F.; Xinli, Z.; Zuliang, L. Catal. Commun. 2008, 9, 317-320.
http://dx.doi.org/10.1016/j.catcom.2007.07.003
[25]. Daniel, R. B.; Neumann, R. Angew. Chem. Int. Ed. 2003, 42, 92-95.
http://dx.doi.org/10.1002/anie.200390062
[26]. Rhule, J. T.; Neiwert, W. A.; Hardcastle, K. I.; Do, B. T.; Hill, C. L. J. Am. Chem. Soc. 2001, 123, 12101-12102.
http://dx.doi.org/10.1021/ja015812p
PMid:11724625
[27]. Chu, W.; Yang, X.; Ye, X.; Wu, Y. Appl. Catal. A: Gen. 1996, 145, 125-140.
http://dx.doi.org/10.1016/0926-860X(96)00109-3
[28]. Giri, B. Y.; Narasimha Rao, K.; Prabhavathi Devi, B. L. A.; Lingaiah, N.; Suryanarayana, I.; Prasad, R. B. N.; Sai Prasad, P. S. Catal. Commun. 2005, 6, 788-792.
http://dx.doi.org/10.1016/j.catcom.2005.08.001
[29]. Giri, B. Y.; Prabhavathi Devi, B. L. A.; Gangadhar, K. N.; Narshimha Rao, K.; Lingaiah, N.; Sai Prasad, P. S.; Prasad, R. B. N. Synth. Commun. 2006, 36, 7-11.
http://dx.doi.org/10.1080/00397910500328266
[30]. Giri, B. Y.; Prabhavathi Devi, B. L. A.; Vijaya lakshmi, K.; Lingaiah, N.; Sai Prasad, P. S.; Prasad, R. B. N. Synth. Commun. 2006, 36, 3797-3801.
http://dx.doi.org/10.1080/00397910600947999
[31]. Giri, B, Y,; Prabhavathi Devi, B. L. A.; Gangadhar, K. N.; Vjaya lakshmi, K.; Lingaiah, N,; Sai Prasad, P. S.; Prasad, R. B. N. Synth. Commun. 2007, 37, 2331-2336.
http://dx.doi.org/10.1080/00397910701410681
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.2.4.495-498.413

















European Journal of Chemistry 2011, 2(4), 495-498 | doi: https://doi.org/10.5155/eurjchem.2.4.495-498.413 | 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.