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

An efficient synthesis of quinoxalines catalyzed by monoammonium salt of 12-tungstophosphoric acid


Vijayalakshmi Kunkuma (1) , Lakshmi Anu Prabhavathi Devi Bethala (2,*) , Yadagiri Bhongiri (3) , Badari Narayana Prasad Rachapudi (4) , Seetharamanjaneya Sai Prasad Potharaju (5)

(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, Accepted: 03 May 2011, Published: 31 Dec 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.

2_4_495_498_800


Keywords


Quinoxalines; Benzil; 1,2-Phenylenediamines; 12-Tungstophosphoric acid; Heteropoly acids; Dichloroethane

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.2.4.495-498.413

Article Metrics


This Abstract was viewed 931 times | PDF Article downloaded 303 times

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]. 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 andbis-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
/


[3]. 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
/


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


[5]. 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
/


[6]. 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
/


[7]. 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


Kunkuma, V.; Bethala, L.; Bhongiri, Y.; Rachapudi, B.; Potharaju, S. Eur. J. Chem. 2011, 2(4), 495-498. doi:10.5155/eurjchem.2.4.495-498.413
Kunkuma, V.; Bethala, L.; Bhongiri, Y.; Rachapudi, B.; Potharaju, S. An efficient synthesis of quinoxalines catalyzed by monoammonium salt of 12-tungstophosphoric acid. Eur. J. Chem. 2011, 2(4), 495-498. doi:10.5155/eurjchem.2.4.495-498.413
Kunkuma, V., Bethala, L., Bhongiri, Y., Rachapudi, B., & Potharaju, S. (2011). An efficient synthesis of quinoxalines catalyzed by monoammonium salt of 12-tungstophosphoric acid. European Journal of Chemistry, 2(4), 495-498. doi:10.5155/eurjchem.2.4.495-498.413
Kunkuma, Vijayalakshmi, Lakshmi Anu Prabhavathi Devi Bethala, Yadagiri Bhongiri, Badari Narayana Prasad Rachapudi, & Seetharamanjaneya Sai Prasad Potharaju. "An efficient synthesis of quinoxalines catalyzed by monoammonium salt of 12-tungstophosphoric acid." European Journal of Chemistry [Online], 2.4 (2011): 495-498. Web. 17 Sep. 2019
Kunkuma, Vijayalakshmi, Bethala, Lakshmi, Bhongiri, Yadagiri, Rachapudi, Badari, AND Potharaju, Seetharamanjaneya. "An efficient synthesis of quinoxalines catalyzed by monoammonium salt of 12-tungstophosphoric acid" European Journal of Chemistry [Online], Volume 2 Number 4 (31 December 2011)

DOI Link: https://doi.org/10.5155/eurjchem.2.4.495-498.413

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  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 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.