European Journal of Chemistry

FeCl3-catalysed C-N coupling reaction between cyclic ethers and heterocyclic amines

Article Sidebar

PDF
Published: Dec 31, 2014
DOI: https://doi.org/10.5155/eurjchem.5.4.612-617.1108
Keywords:
Catalysis, Androgenic alopecia, Anti-Cholinergic drug, FeCl3-catalysed C-N coupling, 2-Hydroxypiperidine analogs, 2-Hydroxypyrrolidine analogs
Section
Research Article
Issue
Vol. 5 No. 4 (2014): December 2014
Dates
Received 2014-06-11
Accepted 2014-07-18
Published 2014-12-31


Main Article Content

Suresh Mani
Post Graduate and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Bharathidasan University, Tiruchirappalli, 620020, Tamil Nadu, India
Mashood Ahamed Fazul Mohamed
Post Graduate and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Bharathidasan University, Tiruchirappalli, 620020, Tamil Nadu, India
Abdul Khader Karakkakal
Post Graduate and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Bharathidasan University, Tiruchirappalli, 620020, Tamil Nadu, India
Syed Ali Padusha Mohamed Khan
Post Graduate and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Bharathidasan University, Tiruchirappalli, 620020, Tamil Nadu, India

Abstract

A series of 2-hydroxypyrrolidine/piperidine derivatives (4a-h)/(4i-m) were prepared by reacting 2,3-dihydrofuran (2a)/3,4-dihydro-2H-pyran (2b) with various heterocyclic amines (3a-h), using FeCl3.6H2O as catalyst. The synthesized compounds were characterized by various physic chemical techniques such as elemental analysis and spectral analysis viz, 1H NMR, 13C NMR and Mass.


icon graph This Abstract was viewed 2294 times | icon graph Article PDF downloaded 920 times

How to Cite
(1)
Mani, S.; Mohamed, M. A. F.; Karakkakal, A. K.; Khan, S. A. P. M. FeCl3-Catalysed C-N Coupling Reaction Between Cyclic Ethers and Heterocyclic Amines. Eur. J. Chem. 2014, 5, 612-617.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Lemos, V. A.; Santos, M. S.; Santos, E. S.; Santos, M. J. S.; Dos Santos, W. N. L.; Souza, A. S.; De Jesus, D. S.; DasVirgens, C. F.; Carvalho, M. S.; Oleszczuk, N.; Vale, M. G. R.; Welz, B.; Ferreira, S. L. C. Spectrochim. Acta B 2007, 62, 4-12.

[2]. Eleonora, D. I.; Nevena, I. P.; Rositca, D. N. Molecules 2012, 17, 4936-4949.
http://dx.doi.org/10.3390/molecules17054936

[3]. Sun, N.; Li, B.; Shao, J.; Mo, W.; Hu, B.; Shen, Z.; Hu, X. Beilstein J. Org. Chem. 2012, 8, 61-70.
http://dx.doi.org/10.3762/bjoc.8.6

[4]. Orvieto, F.; Branca, D.; Giomini, C.; Jones, P.; Koch, U.; Ontoria, J. M.; Palumbi, M. C.; Rowley, M.; Toniatti, C.; Muraglia, E. Bioorg. Med. Chem. Lett. 2009, 19, 4196-4200.
http://dx.doi.org/10.1016/j.bmcl.2009.05.113

[5]. David, G. I. K. J. Nat. Prod. 2009, 72, 507-515.
http://dx.doi.org/10.1021/np800568j

[6]. Sohl, W. E.; Shriner, R. L. J. Am. Chem. Soc. 1933, 55(9), 3828-3833.
http://dx.doi.org/10.1021/ja01336a066

[7]. Berding, G.; Gratz, K. F.; Kolbe, H.; Meyar, G. J.; Dengler, R.; Knoop, B. O.; Hundeshagen, H. Nuklearmedizin. 1994, 33, 194-199.

[8]. Ito, A.; Ohno, Y.; Nakamura, M. J. Pharmacol. Exp. Ther. 2010, 334, 171-181.
http://dx.doi.org/10.1124/jpet.110.167346

[9]. Gasparini, F.; Di Paolo, T.; Gomez-Mancilla, B. Parkinsons Dis. 2013, 2013, Article ID 196028, 11 pages.

[10]. Jakobsen, S. M.; Kersten, H.; Molden. E. J. Am. Geriatr. Soc. 2011, 59, 501-505.
http://dx.doi.org/10.1111/j.1532-5415.2010.03307.x

[11]. Imai, S.; Saito, S.; Takase, H.; Enomoto, M.; Aoyama, H.; Yamaji, S.; Yokoyama, K.; Yagi, H.; Kushiro, T.; Hirayama, T. Circ. J. 2008, 72, 709-715.
http://dx.doi.org/10.1253/circj.72.709

[12]. Nelson, M. Aust. Prescr. 2010, 33, 108-112.

[13]. Altman, D.; Granath, F.; Mattiasson, A.; Falconer, C. Int. Urogynecol. J. 2009, 20, 1285-1291.
http://dx.doi.org/10.1007/s00192-009-0957-z

[14]. Jha, S.; Parsons, M. ClinInterv Aging. 2006, 1, 309-316.
http://dx.doi.org/10.2147/ciia.2006.1.4.309

[15]. Staskin, D. R.; MacDiarmid, S. A. Am. J. Med. 2006, 119, 9-15.
http://dx.doi.org/10.1016/j.amjmed.2005.12.011

[16]. Areej, M. A. H.; Fatma, U. A.; Mutasem, O. T. J. Mol. Graphics Model. 2007, 26, 443-456.
http://dx.doi.org/10.1016/j.jmgm.2007.02.002

[17]. Liu, Y.; Zhang, J.; Xu, W. Curr. Med. Chem. 2007, 14, 2872-2891.
http://dx.doi.org/10.2174/092986707782360024

[18]. Zhang, A.; Xu, W. Mini-Rev. Med. Chem. 2006, 6, 429-448.
http://dx.doi.org/10.2174/138955706776361475

[19]. Anderson, J. M. Am. Fam. Physician. 2007, 75(6), 875-882.

[20]. Bais, J. M.; Eskes, M.; Pel, M.; Bonsel, G. J.; Bleker, O. P. Eur. J. Obstet. Gynecol. Reprod. Biol. 2004, 115, 166-172.

[21]. Magann, E. F.; Evans, S.; Chauhan, S. P.; Lanneau, G.; Fisk, A. D.; Morrison, J. C. Obstet. Gynecol. 2005, 105, 290-293.
http://dx.doi.org/10.1097/01.AOG.0000151993.83276.70

[22]. Anderson, J. M.; Etches, D. Am. Fam. Physician. 2007, 75, 875-882.

[23]. Reyes, O. A.; Gonzalez, G. M. J ObstetGynaecol Can. 2011, 33(11), 1099-1104.

[24]. Gimpl, G.; Postina, R.; Fahrenholz, F.; Reinheimer, T. Eur. J. Pharmacol. 2005, 510(1-2), 9-16.
http://dx.doi.org/10.1016/j.ejphar.2005.01.010

[25]. Osvaldo, A.; Reyes, M. D.; Geneva, M.; Gonzalez, M. D. J. Obstet. Gynaecol. Can. 2011, 33(11), 1099-1104.

[26]. Chouthaiwale, P. V.; Kotkar, S. P.; Sudalai, A. Arkivoc 2009, 2, 88-94.
http://dx.doi.org/10.3998/ark.5550190.0010.210

[27]. Dhawan, P.; Bell, A.; Kumar, A.; Golden, C.; Metha, K. D. J. Lipid Res. 1999, 40, 1911-1919.

[28]. Ahren, B.; Landin-Olsson, M.; Jansson, PA.; Svensson, M.; Holmes, D.; Schweizer, A. J. Clin. Endocrinol. Metab. 2004, 89(5), 2078-2084.
http://dx.doi.org/10.1210/jc.2003-031907

[29]. Attilakos, G.; Psaroudakis, D.; Ash, J.; Buchanan, R.; Winter, C.; Donald, F.; Hunt, L. P.; Draycotta, T. Int. J.Gynaecol. Obstet. 2010, 117(8), 929-936.
http://dx.doi.org/10.1111/j.1471-0528.2010.02585.x

[30]. Dunning, B. E.; Gerich J. E. Endocrine Rev.2007, 28, 3253-3283.
http://dx.doi.org/10.1210/er.2006-0026

[31]. Reddy, K. R.; Krishna, G. G.; Rajasekhar, C. V. Synth. Commun. 2007, 37, 4289-4299.
http://dx.doi.org/10.1080/00397910701575335

[32]. Bhanja, C.; Jena, S.; Nayak, S.; Mohapatra, S. Beilstein. J. Org. Chem. 2012, 8, 1668-1694.
http://dx.doi.org/10.3762/bjoc.8.191

[33]. Matthew, J.; Gaunt, C. C.; Johansson, A. M.; Ngoc T. V. Drug Discov. Today 2007, 12, 8-27.
http://dx.doi.org/10.1016/j.drudis.2006.11.004

[34]. Paterson, S. Br. J. Clin. Pharmacol. 1992, 33, 449-450.
http://dx.doi.org/10.1111/j.1365-2125.1992.tb04066.x

[35]. Arnsten, A. F.; Li, B. M. Biol. Psychiat. 2004, 57(11), 1377-1384.
http://dx.doi.org/10.1016/j.biopsych.2004.08.019

[36]. Kimko, H. C.; Cross, J. T.; Abernethy, D. R. Clin. Pharmacokinet. 1999, 37, 457-470.
http://dx.doi.org/10.2165/00003088-199937060-00002

[37]. Markowitz, J. S.; Devane, C. L.; Boulton, D. W.; Nahas, Z.; Risch, S. C.; Diamond, F.; Patrick, K. S. Drug Metab. Dispo. 2000, 28, 620-624.

[38]. David, H.; Kim, D. H.; Vaccaro, A. R. Spine J. 2006, 6, 479-487.
http://dx.doi.org/10.1016/j.spinee.2006.06.050

[39]. Singh, M.; Magon, N.; Singh, T. J. Midlife Health. 2013, 3, 76-80.

[40]. Report of a WHO Study Group. World Health Organ Tech. Rep. Ser. 1994, 843, 1-129.

[41]. Scow, D. T.; Nolte, R. S.; Shaughnessy, A. F. Am. Fam. Physician. 1999, 59, 2189-2194.

[42]. Balakrishnan, P.; Shanmugam, S.; Lee, W. S.; Lee, W. M.; Kim, J. O.; Oh, D. H.; Kim, D.; Kim, J. S.; Yoo, B. K.; Choi, H.; Woo, J. S.; Yong, C. S. Int. J. Pharm. 2009, 377, 1-8.
http://dx.doi.org/10.1016/j.ijpharm.2009.04.020

[43]. Varma, P. P.; Mahadevan, K. M.; Khader, A.; Hulikal, V. Org. Comm. 2011, 4(3), 52-57.

Supporting Agencies

University Grants Commission, New Delhi, Major Research Project (Ref. No, 41-261/2012 (SR), Dated, 13-07-2012), Sophisticated Test and Instrumentation Centre (STIC), Cochin and Sophisticated Analytical Inst. Fac., Indian Institute of Technology, India
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 © 2025 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).