European Journal of Chemistry

Eaton’s reagent catalysed alacritous synthesis of 3-benzazepinones

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Published: Dec 31, 2016
DOI: https://doi.org/10.5155/eurjchem.7.4.391-396.1477
Keywords:
Alacritous, Eaton’s reagent, 3-Benzazepinone, Solvent free reaction, Methane sulfonic acid, Phosphorous pentoxide
Section
Research Article
Issue
Vol. 7 No. 4 (2016): December 2016
Dates
Received 2016-07-13
Accepted 2016-08-07
Published 2016-12-31


Main Article Content

Shubhavathi Thimmaiah
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, 570006, Karnataka, India
Mallesha Ningegowda
Research and Development Centre, Chethan Joshi Exports Biochem Pvt. Ltd., Bommanahalli, Bangalore, 560068, India
Nanjunda Swamy Shivananju
Department of Biotechnology, JSS Science and Technology University, JSS Technical Institutions Campus, Mysuru, 570006, Karnataka, India
Raghu Ningegowda
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, 570006, Karnataka, India
Ranjith Siddaraj
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, 570006, Karnataka, India
Babu Shubha Priya
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, 570006, Karnataka, India

Abstract

An expeditious method for the synthesis of 3-benzazepinones has been developed by using a mixture of phosphorus pentoxide-methane sulfonic acid (Eaton’s reagent) at room temperature under solvent and metal catalyst free condition. Wide functional group tolerance, mild reaction conditions, simple procedure, ease of work-up and high yields is the citable features of this protocol.


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(1)
Thimmaiah, S.; Ningegowda, M.; Shivananju, N. S.; Ningegowda, R.; Siddaraj, R.; Priya, B. S. Eaton’s Reagent Catalysed Alacritous Synthesis of 3-Benzazepinones. Eur. J. Chem. 2016, 7, 391-396.

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References

[1]. Lewis, H. D.; Perez-Revuetta, B. I.; Nadin, A.; Neduvelil, J. G.; Harrison, T.; Pollack, S. J.; Slearman, M. S. Biochemistry-US. 2003, 42, 7580-7586.
http://dx.doi.org/10.1021/bi034310g

[2]. Bisi, A.; Rampa, A.; Badriesi, R.; Gobbi, S.; Belluti, F.; Loan, P.; Varoti, E.; Chiarini, A.; Valenti, P. Bioorg. Med. Chem. Lett. 2003, 11, 1353-1361.
http://dx.doi.org/10.1016/S0968-0896(02)00621-1

[3]. Gnanalingaham, K. K.; Hunter, A. J.; Jenner, P.; Marsden, C. D. Psychopharmacology (Berl). 1995, 117, 403-412.
http://dx.doi.org/10.1007/BF02246211

[4]. Le-Diguarher, T.; Ortuno, J. C.; Shanks, D.; Guilbaud, N.; Pierre, A.; Raimbaud, E.; Fauchere, J. L.; Hickman, J. A.; Tucker, G. C.; Casara, P. J. Bioorg. Med. Chem. Lett. 2004, 14, 767-771.
http://dx.doi.org/10.1016/j.bmcl.2003.11.013

[5]. Daemmgen, J.; Guth, B.; Seidler, R. WO 0178699 A2 20011025: PCT Int. Appl. 2001, 13.

[6]. Reiffen, M.; Eberlein, W.; Muller, P.; Psiorz, M.; Noll, K.; Heider, J.; Lillie, C.; Kobinger, W.; Luger, P. J. Med. Chem. 1990, 33, 1496-1504.
http://dx.doi.org/10.1021/jm00167a033

[7]. Michellys, P. V. U. S. Patent 0176881, 2008.

[8]. Giles, B. C. U. S. Patent 0038376, 2008.

[9]. Zhang, L.; Ye, D.; Zhou, Y.; Liu, G.; Feng, E.; Jiang, H.; Liu, H. J. Org. Chem. 2010, 75, 3671-3671.
http://dx.doi.org/10.1021/jo100378u

[10]. Ishihara, Y.; Tanaka, T.; Miwatashi, S.; Fujishima, A.; Goto, G. J. Chem. Soc., Perkin Trans. 1994, 1, 2993-2999.
http://dx.doi.org/10.1039/P19940002993

[11]. Guastavino, J. F.; Buden, M. E.; Garcia, C. S.; Rossi, R. A. Arkivoc 2011, 7, 389-405.

[12]. Sarkar, S.; Husain, S. M.; Schepmann, D.; Frohlich, R.; Wunsch, B. Tetrahedron 2012, 68, 2687-2695.
http://dx.doi.org/10.1016/j.tet.2012.01.052

[13]. Wang, M.; Gao, M.; Steele, B. L.; Glick-Wilson, B. E.; Brown-Proctor, C.; Shekhar, A.; Hutchins, G. D.; Zheng, Q. H.; Bioorg. Med. Chem. Lett. 2012, 22, 4713-4718.
http://dx.doi.org/10.1016/j.bmcl.2012.05.076

[14]. Kato, H.; Kobayashi, T.; Horie, K.; Oguri, K.; Moriwaki, M. J. Chem. Soc., Perkin Trans. 1993, 1, 1055-1059.
http://dx.doi.org/10.1039/P19930001055

[15]. Borse, A. R.; Pail, M. N.; Patil, N.; Tetgure. S. R. Heterocyclic Lett. 2012, 2, 277-282.

[16]. Eaton, P. E.; Carlson, G. R.; Lee, J. T. J. Org. Chem. 1973, 38, 4071-4073.
http://dx.doi.org/10.1021/jo00987a028

[17]. Borse, A. R.; Patil, M.; Patil, N.; Shinde, R. ISRN Org. Chem. 2012, 2012, Article ID: 415645, 1-6 pages.

[18]. Zewge, D.; Chen, C. Y.; Deer, C.; Dormer, P. G.; Hughes, D. L. J. Org. Chem. 2007, 72, 4276-4279.
http://dx.doi.org/10.1021/jo070181o

[19]. Fomenkov, A. I.; Blagodatskikh, I. V.; Ponomarev, I. I.; Volkova, Y. A.; Ponomarev, I. I.; Khokhlov, A. R. Polym. Sci. Ser. B+ 2009, 51, 166-173.
http://dx.doi.org/10.1134/S1560090409050030

[20]. Park, S. J.; Lee, J. C.; Lee, K. I. Bull. Korean Chem. Soc. 2007, 28, 1203-1205.
http://dx.doi.org/10.5012/bkcs.2007.28.7.1203

[21]. Leemans, E.; D'hooghe, M.; Kimpe, N. D. Chem. Rev. 2011, 111, 3268-3333.
http://dx.doi.org/10.1021/cr100295j

[22]. Pandit, C. R.; Polniaszek, R. P.; Thottthil, J. K. Synth. Commun. 2002, 32, 2427-2432.
http://dx.doi.org/10.1081/SCC-120006015

[23]. Kaboudin, B.; Abedi, Y. Synthesis 2009, 12, 2025-2028.
http://dx.doi.org/10.1055/s-0029-1216790

[24]. Mcgarry, L. W.; Detty, M. R. J. Org. Chem. 1990, 55, 4349-4356.
http://dx.doi.org/10.1021/jo00301a027

[25]. Tupare, S. D.; Nagale, S. V.; Bobe, S. R.; Hallale, S. N.; Bhosale, S. V.; Vyawahare, S. K.; Dhake, S. A.; Bhosale, S. V.; Pawar, R. P. Lett. Org. Chem. 2012, 9, 526-529.
http://dx.doi.org/10.2174/157017812802139627

[26]. Borse, A. R.; Patil, M. N.; Patil, N. L. Electron. J. Chem. 2012, 9, 1313-1319.

Supporting Agencies

Science and Engineering Research Board, New Delhi [Start-Up-Research Grant (Young Scientists)-Life Sciences] No, SB/FT/LS-297/2012] and University Grants Commission, New Delhi, Govt. of India under UGC-MRP vide No. F. No, 41/224/2012 (SR).
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