European Journal of Chemistry 2013, 4(4), 422-424 | doi: https://doi.org/10.5155/eurjchem.4.4.422-424.857 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Gangadhar Asaram Meshram (1,*) , Shruti Shashank Deshpande (2) , Vipul Amratlal Vala (3) , Pramod Arun Wagh (4)

(1) Department of Chemistry, University of Mumbai, Vidyanagri, Kalina, Santacruz (E), Mumbai-400098, India
(2) Department of Chemistry, University of Mumbai, Vidyanagri, Kalina, Santacruz (E), Mumbai-400098, India
(3) Department of Chemistry, University of Mumbai, Vidyanagri, Kalina, Santacruz (E), Mumbai-400098, India
(4) Department of Chemistry, University of Mumbai, Vidyanagri, Kalina, Santacruz (E), Mumbai-400098, India
(*) Corresponding Author

Received: 15 Jun 2013 | Revised: 19 Jul 2013 | Accepted: 22 Jul 2013 | Published: 31 Dec 2013 | Issue Date: December 2013

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

Keywords


1,2-Diamines; 1,2-Dicarbonyls; Indion 190 resin; Solid acid catalyst; Quinoxaline derivatives; Substituted pyrido-pyrazines

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.4.4.422-424.857

Links for Article


| | | | | | |

| | | | | | |

| |

Related Articles




Article Metrics

This Abstract was viewed 1141 times | PDF Article downloaded 469 times

Funding information


Department of Chemistry, University of Mumbai, Vidyanagri, Kalina, Santacruz (E), Mumbai-400098, India

Citations

/


[1]. Toni Hille, Torsten Irrgang, Rhett Kempe
The Synthesis of Benzimidazoles and Quinoxalines from Aromatic Diamines and Alcohols by Iridium-Catalyzed Acceptorless Dehydrogenative Alkylation
Chemistry - A European Journal  20(19), 5569, 2014
DOI: 10.1002/chem.201400400
/


[2]. Venkata Krishna Reddy Motakatla, Anusha Gokanapalli, Vasu Govardhana Reddy Peddiahgari
Cu–N‐heterocyclic carbene‐catalysed synthesis of 2‐aryl‐3‐(arylethynyl)quinoxalines from one‐pot tandem coupling of o ‐phenylenediamines and terminal alkynes
Applied Organometallic Chemistry  33(11), , 2019
DOI: 10.1002/aoc.5188
/


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

How to cite


Meshram, G.; Deshpande, S.; Vala, V.; Wagh, P. Eur. J. Chem. 2013, 4(4), 422-424. doi:10.5155/eurjchem.4.4.422-424.857
Meshram, G.; Deshpande, S.; Vala, V.; Wagh, P. Indion 190 resin: Reusable catalyst for the synthesis of quinoxalines and pyrido-pyrazines at ambient temperature. Eur. J. Chem. 2013, 4(4), 422-424. doi:10.5155/eurjchem.4.4.422-424.857
Meshram, G., Deshpande, S., Vala, V., & Wagh, P. (2013). Indion 190 resin: Reusable catalyst for the synthesis of quinoxalines and pyrido-pyrazines at ambient temperature. European Journal of Chemistry, 4(4), 422-424. doi:10.5155/eurjchem.4.4.422-424.857
Meshram, Gangadhar, Shruti Shashank Deshpande, Vipul Amratlal Vala, & Pramod Arun Wagh. "Indion 190 resin: Reusable catalyst for the synthesis of quinoxalines and pyrido-pyrazines at ambient temperature." European Journal of Chemistry [Online], 4.4 (2013): 422-424. Web. 28 Nov. 2020
Meshram, Gangadhar, Deshpande, Shruti, Vala, Vipul, AND Wagh, Pramod. "Indion 190 resin: Reusable catalyst for the synthesis of quinoxalines and pyrido-pyrazines at ambient temperature" European Journal of Chemistry [Online], Volume 4 Number 4 (31 December 2013)

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.4.4.422-424.857

| | | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2013, 4(4), 422-424 | doi: https://doi.org/10.5155/eurjchem.4.4.422-424.857 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  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 2010-2020 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.