European Journal of Chemistry

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

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Published: Mar 31, 2013
DOI: https://doi.org/10.5155/eurjchem.4.1.61-63.732
Keywords:
Magnesium, Nitroarenes, Azocompounds, Ammonium bromide, Reductive dimerization, Catalytic transfer hydrogenation
Section
Research Article
Issue
Vol. 4 No. 1 (2013): March 2013
Dates
Received 2013-01-02
Accepted 2013-01-20
Published 2013-03-31


Main Article Content

Malavalli Basavaraju Sridhara
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
Ramesh Suhas
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India
Dase Gowda Channe Gowda
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570006, Karnataka, India

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.

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Sridhara, M. B.; Suhas, R.; Gowda, D. G. C. Synthesis of Azoarenes by Reductive Dimerization of Nitroarenes Using Ammonium Bromide and Magnesium. Eur. J. Chem. 2013, 4, 61-63.

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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.

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