European Journal of Chemistry

Indion 190 resin: Reusable catalyst for the synthesis of quinoxalines and pyrido-pyrazines at ambient temperature



Main Article Content

Gangadhar Asaram Meshram
Shruti Shashank Deshpande
Vipul Amratlal Vala
Pramod Arun Wagh

Abstract

An efficient method for synthesis of quinoxalines and substituted pyrido-pyrazines has been developed from different 1,2-dicarbonyl compounds and substituted 1,2-diamines using Indion 190 resin as a solid acid catalyst. Ambient reaction conditions, high product yield and reusability of the catalyst with minimal loading are the salient features of the present protocol.

4_4_422_424

icon graph This Abstract was viewed 1933 times | icon graph Article PDF downloaded 856 times

How to Cite
(1)
Meshram, G. A.; Deshpande, S. S.; Vala, V. A.; Wagh, P. A. Indion 190 Resin: Reusable Catalyst for the Synthesis of Quinoxalines and Pyrido-Pyrazines at Ambient Temperature. Eur. J. Chem. 2013, 4, 422-424.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Clauss, E.; Seipelt, I.; Gunther, E.; Polymeropoulos, E.; Czech, M.; Schuster, T. PCT Int. Appl. W02007/054556 2007; Chem. Abstr. 2007, 146, 521825.

[2]. Lindsley, C. W.; Zhao, Z.; Leister, W. H.; Robinson, R. G.; Barnett, S. F.; Defeojones, D.; Jones, R. E.; Hartmann, G. D.; Huff, J. R.; Huber, H.; Duggan, M. E. Bioorg. Med. Chem. Lett. 2005, 15, 761-764.
http://dx.doi.org/10.1016/j.bmcl.2004.11.011
PMid:15664853

[3]. Loriga, M.; Piras, S.; Sanna, P.; Paglietti, G. Farmaco 1997, 52(3), 157-166.
PMid:9212450

[4]. Seitz, L. E.; Suling, W. J.; Renoylds, R. C. J. Med. Chem. 2002, 45, 5604-5606.
http://dx.doi.org/10.1021/jm020310n

[5]. He, W.; Meyers, M. R.; Hanney, B.; Spada, A.; Blider, G.; Galzeinski, H.; Amin, D.; Needle, S.; Page, K.; Jayyosi, Z.; Perrone, H. Bioorg. Med. Chem. Lett. 2003, 13, 3091-3095.
http://dx.doi.org/10.1016/S0960-894X(03)00654-1

[6]. Kim, Y. B.; Kim, Y. H.; Park, J. Y.; Kim, S. K. Bioorg. Med. Chem. Lett. 2004, 14, 541-544.
http://dx.doi.org/10.1016/j.bmcl.2003.09.086
PMid:14698199

[7]. Katoh, A.; Yoshida, T.; Ohkanda, J. Heterocycles 2000, 52, 911‐920.
http://dx.doi.org/10.3987/COM-99-S61

[8]. Dailey, S.; Feast, W. J.; Peace, R. J.; Sage, I. C.; Till, S.; Wood, E. L. Chem. Mater. 2001, 11, 2238-2243.
http://dx.doi.org/10.1039/b104674h

[9]. Crossley, M. J.; Johnston, L. A. Chem. Commun. 2002, 1122-1123.
http://dx.doi.org/10.1039/b111655j

[10]. Brown, D. J., Quinoxalines: SUPPLEMENT II, in The Chemistry of Heterocyclic Compounds, Taylor, E. C., Wipf, P. (Eds.). John Wiley and Sons, New Jersey, 2004.

[11]. Morales-Castellanos, J. J.; Ramirez-Hernandez, K.; Gomez-Flores, N. S.; Rodas-Saurez, O. R. Peralta-Cruz, J. Molecules 2012, 17, 5164-5176.
http://dx.doi.org/10.3390/molecules17055164
PMid:22628038

[12]. Zhang, X. Z.; Wang, J. X.; Sun, Y. J.; Zhan, H. W. Chinese Chem. Lett. 2010, 21, 395-398.
http://dx.doi.org/10.1016/j.cclet.2009.12.015

[13]. Robinson, R. S.; Taylor, R. J. K. Synlett. 2005, 6, 1003-1005.

[14]. More, S. V.; Sastry, M. N. V.; Yao, C. F. Green Chem. 2006, 8, 91-95.
http://dx.doi.org/10.1039/b510677j

[15]. 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

[16]. Darbari, H. R.; Mohandessi, S.; Aghapoor, K.; Mohsenzadeh, F. Catal. Commun. 2007, 8, 389-392.
http://dx.doi.org/10.1016/j.catcom.2006.06.033

[17]. Huang, T. K.; Wang, R.; Shi, L.; Lu, X. X. Catal. Commun. 2008, 9, 1143-1147.
http://dx.doi.org/10.1016/j.catcom.2007.10.024

[18]. Hazarika, P.; Gogoi, P.; Konwar, D. Synth. Commun. 2007, 37, 3447-3454.
http://dx.doi.org/10.1080/00397910701489388

[19]. 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

[20]. Cai, J. J.; Zou, J. P.; Pan, X. Q.; Zhang, W. Tetrahedron Lett. 2008, 49, 7386-7390.
http://dx.doi.org/10.1016/j.tetlet.2008.10.058

[21]. Das, B.; Katta, V.; Kanaparthy, S.; Anjoy, M. Tetrahedron Lett. 2007, 48, 5371-5374.
http://dx.doi.org/10.1016/j.tetlet.2007.06.036

[22]. Madhav, B.; Murthy, S. N.; Reddy, V. P.; Rao, K. R.; Nageshwar, Y. V. D. Tetrahedron Lett. 2009, 50, 6025-6028.
http://dx.doi.org/10.1016/j.tetlet.2009.08.033

[23]. Rao, K. T. V.; Sai Prasad, P. S.; Lingaiah, N. J. Mol. Catal. A-Chem. 2009, 312, 65-69.
http://dx.doi.org/10.1016/j.molcata.2009.07.005

[24]. Krishnakumar, B.; Swaminathan, M. J. Organomet. Chem. 2010, 695, 2572-2577.
http://dx.doi.org/10.1016/j.jorganchem.2010.08.055

[25]. Katkar, S. S.; Mohite, P. H.; Gadekar, L. S.; Arbad, B. R.; Lande, M. K. Cent. Eur. J. Chem. 2010, 8, 320-325.
http://dx.doi.org/10.2478/s11532-009-0151-7

[26]. Darbari, H. R.; Aghapoor, K.; Mohsenzadeh, F.; Tala, F.; Asadollahnejad, N.; Badiei, A. Catal. Lett. 2009, 133, 84-89.
http://dx.doi.org/10.1007/s10562-009-0161-2

[27]. Srinivasula, R. L.; Gangi, R. N. C.; Ram, R. T.; Lingappa, Y.; Bodireddy, M. R. J. Korean Chem. Soc. 2011, 55, 304-307.
http://dx.doi.org/10.5012/jkcs.2011.55.2.304

[28]. Chaskar, A.; Yewale, S.; Langi, B.; Deokar, H. J. Korean Chem. Soc. 2009, 53, 422-426.
http://dx.doi.org/10.5012/jkcs.2009.53.4.422

[29]. Kaupp, G.; Reza Naimi-Jamal, M. Eur. J. Org. Chem. 2002, 8, 1368-1373.
http://dx.doi.org/10.1002/1099-0690(200204)2002:8<1368::AID-EJOC1368>3.0.CO;2-6

[30]. Deady, L. W.; Desneves, J.; Ross A. C. Tetrahedron 1993, 49, 9823-9828.
http://dx.doi.org/10.1016/S0040-4020(01)80184-8

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).