European Journal of Chemistry

Eaton’s reagent catalysed alacritous synthesis of 3-benzazepinones



Main Article Content

Shubhavathi Thimmaiah
Mallesha Ningegowda
Nanjunda Swamy Shivananju
Raghu Ningegowda
Ranjith Siddaraj
Babu Shubha Priya

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.


icon graph This Abstract was viewed 2508 times | icon graph Article PDF downloaded 1095 times

How to Cite
(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.

Article Details

Share
Crossref - Scopus - Google - European PMC
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).
Most read articles by the same author(s)

Most read articles by the same author(s)

TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).