

FeCl3-catalysed C-N coupling reaction between cyclic ethers and heterocyclic amines
Suresh Mani (1)




(1) Post Graduate and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Bharathidasan University, Tiruchirappalli, 620020, Tamil Nadu, India
(2) Post Graduate and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Bharathidasan University, Tiruchirappalli, 620020, Tamil Nadu, India
(3) Post Graduate and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Bharathidasan University, Tiruchirappalli, 620020, Tamil Nadu, India
(4) Post Graduate and Research Department of Chemistry, Jamal Mohamed College (Autonomous), Bharathidasan University, Tiruchirappalli, 620020, Tamil Nadu, India
(*) Corresponding Author
Received: 11 Jun 2014 | Accepted: 18 Jul 2014 | Published: 31 Dec 2014 | Issue Date: December 2014
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.
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European Journal of Chemistry
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DOI: 10.5155/eurjchem.5.4.612-617.1108
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Funding information
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
Citations
[1]. Sujit K. Ghorai, Vijaya G. Gopalsamuthiram, Anup M. Jawalekar, Rupesh E. Patre, Sitaram Pal
Iron catalyzed C N bond formation
Tetrahedron 73(14), 1769, 2017
DOI: 10.1016/j.tet.2017.02.033

[2]. Sergio L. Laurella, Mauricio F. Erben
Comment on “Structural and vibrational studies on 1-(5-Methyl- [1,3,4] thiadiazol-2-yl)-pyrolidin-2-ol” [Spectrochimica Acta Part A, 152 (2016) 252–261]. The importance of intramolecular OH⋯N hydrogen bonding in the conformational properties of thiadiazol-pyrrolidin-2-ol bearing species
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 164, 40, 2016
DOI: 10.1016/j.saa.2016.03.018

[3]. N. Ramesh Babu, H. Saleem, S. Subashchandrabose, M. Syed Ali Padusha, S. Bharanidharan
Structural and vibrational studies on 1-(5-methyl-[1,3,4] thiadiazol-2-yl)-pyrolidin-2-ol
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 152, 252, 2016
DOI: 10.1016/j.saa.2015.06.112

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.
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