European Journal of Chemistry 2013, 4(1), 61-63 | doi: https://doi.org/10.5155/eurjchem.4.1.61-63.732 | Get rights and content

Issue cover





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

Synthesis of azoarenes by reductive dimerization of nitroarenes using ammonium bromide and magnesium


Malavalli Basavaraju Sridhara (1) , Ramesh Suhas (2) , Dase Gowda Channe Gowda (3,*)

(1) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(2) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(3) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
(*) Corresponding Author

Received: 02 Jan 2013 | Revised: 19 Jan 2013 | Accepted: 20 Jan 2013 | Published: 31 Mar 2013 | Issue Date: March 2013

Abstract


A simple and efficient protocol for the synthesis of symmetrically substituted azoarenes from nitroarenes by using ammonium bromide as hydrogen donor and magnesium powder as catalyst at room temperature in methanol media is described. Various azoarenes containing few additional substituents such as halogen, methyl, hydroxyl, methoxy, ethoxy etc. functions have been synthesized in a single step by the use of this reagent. The conversion is clean, rapid, chemo-selective and high yielding.

4_1_61_63

Announcements


One of our sponsors will cover the article processing fee for all submissions made between May 17, 2023 and June 16, 2023 (Voucher code: SPONSOR2023).

Editor-in-Chief
European Journal of Chemistry

Keywords


Magnesium; Nitroarenes; Azocompounds; Ammonium bromide; Reductive dimerization; Catalytic transfer hydrogenation

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.4.1.61-63.732

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 2346 times | icon graph PDF Article downloaded 1180 times

Funding information


The University Grants Commission (UGC), New Delhi, India

Citations

/


[1]. Sitaram H. Gund, Radheshyam S. Shelkar, Jayashree M. Nagarkar
An efficient catalyst-free and chemoselective synthesis of azobenzenes from nitrobenzenes
RSC Adv.  4(81), 42947, 2014
DOI: 10.1039/C4RA06027J
/


[2]. Ashok Raj Patel, Geetika Patel, Gurupada Maity, Shiv P. Patel, Sumantra Bhattacharya, Anjaneyulu Putta, Subhash Banerjee
Direct Oxidative Azo Coupling of Anilines Using a Self-Assembled Flower-like CuCo2O4 Material as a Catalyst under Aerobic Conditions
ACS Omega  5(47), 30416, 2020
DOI: 10.1021/acsomega.0c03562
/


[3]. Behzad Zeynizadeh, Fariba Faraji
Immobilized antimony species on magnetite: a novel and highly efficient magnetically reusable nanocatalyst for direct and gram-scale reductive-coupling of nitroarenes to azoarenes
RSC Advances  9(23), 13112, 2019
DOI: 10.1039/C9RA01249D
/


References


[1]. Ikeda, T.; Stutsman, O. Science 1995, 268, 1873-1875.
http://dx.doi.org/10.1126/science.268.5219.1873
PMid:17797528

[2]. Liu, Z. F.; Hashimoto, K.; Fujishima, A. Nature 1990, 347, 658-660.
http://dx.doi.org/10.1038/347658a0

[3]. Little, R. D.; Venegas. J. Org. Chem. 1978, 43, 2921-2923.
http://dx.doi.org/10.1021/jo00408a040

[4]. Shine, H. J.; Chamness, J. T. J. Org. Chem. 1963, 28, 1232-1236.
http://dx.doi.org/10.1021/jo01040a016

[5]. Nystrom, R. F.; Brown, W. G. J. Am. Chem. Soc. 1948, 70, 3738-3740.
http://dx.doi.org/10.1021/ja01191a057

[6]. Martynoff, M. Compt. Rend. Acad. Sci. Paris 1946, 223, 747-749.

[7]. Lang-Fugmann, S. In Houben-Weyl Methoden der Organischen Chemie, Band E/6d, Teil 1; Klamann, D., Ed.; Georg Thieme: Stuttgart, 1992; pp. 119-142.

[8]. Vogel, A. I.; Watling, A.; Watling, J. J. Chem. Educ. 1958, 35, 40-40.
http://dx.doi.org/10.1021/ed035p40

[9]. Tadros, W.; Ishak, M. S.; Bassili, E. J. Org. Chem. 1959, 24, 627-629.
http://dx.doi.org/10.1021/jo01087a013

[10]. Moore, R. E.; Furst, A. J. Org. Chem. 1958, 23, 1504-1506.
http://dx.doi.org/10.1021/jo01104a027

[11]. Hutchins, R. O.; Lamson, D. W.; Rua, L.; Cynthia, M.; Bruce, M. J. Org. Chem. 1971, 36, 803-806.
http://dx.doi.org/10.1021/jo00805a015

[12]. Kabalka, G. W.; Varma, R. S. Comprehensive Organic Synthesis, Vol. 8; Pergamon Press: Oxford. 1991, pp. 363-380.
http://dx.doi.org/10.1016/B978-0-08-052349-1.00231-6

[13]. Wada, S.; Urano, M.; Suzuki, H. J. Org. Chem. 2002, 67, 8254-8257.
http://dx.doi.org/10.1021/jo0203645

[14]. Comprehensive Organic Synthesis, Vol. 8; (Reduction) Fleming I., Eds; Pergamon Press: Oxford, 8, 1991, pp. 1-24.

[15]. Rylander, P. N. Hydrogenation Methods, Academic Press: New York. 1985, pp. 365.

[16]. Brieger, O.; Nestrick, T. J. Chem. Rev. 1974, 74, 567-580.
http://dx.doi.org/10.1021/cr60291a003

[17]. Johnstone, R. A. W.; Wibly, A.; Entwistle, I. D. Chem. Rev. 1985, 85, 129-170.
http://dx.doi.org/10.1021/cr00066a003

[18]. Gowda, S.; Gowda, D. C. Synthesis 2002, 4, 460-462.
http://dx.doi.org/10.1055/s-2002-20950

[19]. Pitts, R. M.; Harison, M. R.; Moody, E. J. J Chem. Soc. Perkin Trans I 2001, 9, 955-977.

[20]. Banik, B. K.; Suhendra, M.; Banik, I.; Becker, F. F. Synth. Commun. 2000, 30, 3745-3754.
http://dx.doi.org/10.1080/00397910008087002

[21]. Youn, K. I.; Yon, H. G.; Pak, S. C. Tetrahedron Lett. 1986, 27, 2409-2410.
http://dx.doi.org/10.1016/S0040-4039(00)84542-6

[22]. Proffit, A. J.; Watt, S. D.; Corey, E. J. J. Org. Chem. 1979, 44, 3972-3974.
http://dx.doi.org/10.1021/jo01336a051

[23]. Brettle, R.; Shiobib, M. S. Tetrahedron Lett. 1980, 30, 2915-2916.
http://dx.doi.org/10.1016/S0040-4039(00)78643-6

[24]. Gowda, D. C. Tetrahedron Lett. 2002, 43, 311-313.
http://dx.doi.org/10.1016/S0040-4039(01)02113-X

[25]. Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Indian J. Chem. Sect. B. 2003, 42, 2882-2884.

[26]. Abiraj, K.; Gowda, D. C. Synth. Commun. 2004, 34(4), 599-605.
http://dx.doi.org/10.1081/SCC-120027707

[27]. Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Tetrahedron Lett. 2003, 44, 5835-5837.
http://dx.doi.org/10.1016/S0040-4039(03)01411-4

[28]. Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Aust. J. Chem. 2004, 57, 609-610.
http://dx.doi.org/10.1071/CH03143

[29]. Srinivasa, G. R.; Abiraj, K.; Gowda, D. C. Synth. Commun. 2003, 33, 4221-4227.
http://dx.doi.org/10.1081/SCC-120026850

[30]. Vogel, A. I. Text Book of Practical Organic Chemistry; Addison Wesley Longman Limited: UK, 1997, 1298.


How to cite


Sridhara, M.; Suhas, R.; Gowda, D. Eur. J. Chem. 2013, 4(1), 61-63. doi:10.5155/eurjchem.4.1.61-63.732
Sridhara, M.; Suhas, R.; Gowda, D. Synthesis of azoarenes by reductive dimerization of nitroarenes using ammonium bromide and magnesium. Eur. J. Chem. 2013, 4(1), 61-63. doi:10.5155/eurjchem.4.1.61-63.732
Sridhara, M., Suhas, R., & Gowda, D. (2013). Synthesis of azoarenes by reductive dimerization of nitroarenes using ammonium bromide and magnesium. European Journal of Chemistry, 4(1), 61-63. doi:10.5155/eurjchem.4.1.61-63.732
Sridhara, Malavalli, Ramesh Suhas, & Dase Gowda Channe Gowda. "Synthesis of azoarenes by reductive dimerization of nitroarenes using ammonium bromide and magnesium." European Journal of Chemistry [Online], 4.1 (2013): 61-63. Web. 4 Jun. 2023
Sridhara, Malavalli, Suhas, Ramesh, AND Gowda, Dase. "Synthesis of azoarenes by reductive dimerization of nitroarenes using ammonium bromide and magnesium" European Journal of Chemistry [Online], Volume 4 Number 1 (31 March 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.4.1.61-63.732


CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2013, 4(1), 61-63 | doi: https://doi.org/10.5155/eurjchem.4.1.61-63.732 | 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.