European Journal of Chemistry 2016, 7(4), 391-396. doi:10.5155/eurjchem.7.4.391-396.1477

Eaton’s reagent catalysed alacritous synthesis of 3-benzazepinones


Shubhavathi Thimmaiah (1) , Mallesha Ningegowda (2) , Nanjunda Swamy Shivananju (3) , Raghu Ningegowda (4) , Ranjith Siddaraj (5) , Babu Shubha Priya (6,*)

(1) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, 570006, Karnataka, India
(2) Research and Development Centre, Chethan Joshi Exports Biochem Pvt. Ltd., Bommanahalli, Bangalore, 560068, India
(3) Department of Biotechnology, JSS Science and Technology University, JSS Technical Institutions Campus, Mysuru, 570006, Karnataka, India
(4) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, 570006, Karnataka, India
(5) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, 570006, Karnataka, India
(6) Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru, 570006, Karnataka, India
(*) Corresponding Author

Received: 13 Jul 2016, Accepted: 07 Aug 2016, Published: 31 Dec 2016

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.


Keywords


Alacritous; Eaton’s reagent; 3-Benzazepinone; Solvent free reaction; Methane sulfonic acid; Phosphorous pentoxide

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.7.4.391-396.1477

Article Metrics


This Abstract was viewed 686 times | PDF Article downloaded 313 times

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.


How to cite


Thimmaiah, S.; Ningegowda, M.; Shivananju, N.; Ningegowda, R.; Siddaraj, R.; Priya, B. Eur. J. Chem. 2016, 7(4), 391-396. doi:10.5155/eurjchem.7.4.391-396.1477
Thimmaiah, S.; Ningegowda, M.; Shivananju, N.; Ningegowda, R.; Siddaraj, R.; Priya, B. Eaton’s reagent catalysed alacritous synthesis of 3-benzazepinones. Eur. J. Chem. 2016, 7(4), 391-396. doi:10.5155/eurjchem.7.4.391-396.1477
Thimmaiah, S., Ningegowda, M., Shivananju, N., Ningegowda, R., Siddaraj, R., & Priya, B. (2016). Eaton’s reagent catalysed alacritous synthesis of 3-benzazepinones. European Journal of Chemistry, 7(4), 391-396. doi:10.5155/eurjchem.7.4.391-396.1477
Thimmaiah, Shubhavathi, Mallesha Ningegowda, Nanjunda Swamy Shivananju, Raghu Ningegowda, Ranjith Siddaraj, & Babu Shubha Priya. "Eaton’s reagent catalysed alacritous synthesis of 3-benzazepinones." European Journal of Chemistry [Online], 7.4 (2016): 391-396. Web. 22 Sep. 2019
Thimmaiah, Shubhavathi, Ningegowda, Mallesha, Shivananju, Nanjunda, Ningegowda, Raghu, Siddaraj, Ranjith, AND Priya, Babu. "Eaton’s reagent catalysed alacritous synthesis of 3-benzazepinones" European Journal of Chemistry [Online], Volume 7 Number 4 (31 December 2016)

DOI Link: https://doi.org/10.5155/eurjchem.7.4.391-396.1477

Refbacks

  • There are currently no refbacks.


Bookmark and Share


Copyright (c)



© Copyright 2019 • 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 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.