One-pot, multicomponent synthesis of symmetrical Hantzsch 1,4-dihydropyridine derivatives using glycerol as clean and green solvent

Harvinder Singh Sohal; Arun Goyal; Rajeev Sharma; Rajshree Khare

doi:10.5155/eurjchem.5.1.171-175.943

PDF

Published: Mar 31, 2014

DOI: https://doi.org/10.5155/eurjchem.5.1.171-175.943

Keywords:

One-pot, Glycerol, Aldehydes, Catalyst free, 1, 4-Dihydropyridine, Hantzsch condensation

Section

Research Article

Issue

Vol. 5 No. 1 (2014): March 2014

Dates

Received 2013-10-05
Accepted 2013-11-16
Published 2014-03-31

Harvinder Singh Sohal

Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India

Arun Goyal

Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India

Rajeev Sharma

Department of Chemistry, Multani Mal Modi College, Patiala-147 001, Punjab, India

Rajshree Khare

Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India

Abstract

Multi component, one pot synthesis of symmetrical 1,4-dihydropyridine derivatives from the condensation of ethyl/methyl acetoacetate, aromatic/aliphatic aldehyde and ammonium acetate has been described using glycerol, as economical, easily available and environmentally benign reagent. The targeted molecules were obtained in high purity and excellent yield without use of any additional catalyst and methodology from readily available starting materials.

This Abstract was viewed 4485 times |

Article PDF downloaded 1311 times

How to Cite

(1)

Sohal, H. S.; Goyal, A.; Sharma, R.; Khare, R. One-Pot, Multicomponent Synthesis of Symmetrical Hantzsch 1,4-Dihydropyridine Derivatives Using Glycerol As Clean and Green Solvent. Eur. J. Chem. 2014, 5, 171-175.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Hantzsch, A. Jusfus Liebigs Ann. Chem. 1882, 215, 1-82.
http://dx.doi.org/10.1002/jlac.18822150102

[2]. Hutton, R. F.; Westheimer, F. H. Tetrahedron 1958, 3, 73-74.
http://dx.doi.org/10.1016/S0040-4020(01)82613-2

[3]. Rahway, N. J. The Merck Index, 12th edition, Merck Research Laboratories, 1996.

[4]. Bostrom, S. L.; Ljung, B.; Mardh, S.; Forsen, S.; Thulin, E. Nature 1981, 292, 777-778.
http://dx.doi.org/10.1038/292777a0

[5]. Iwanami, M.; Shibanuma, T.; Fujimoto, M.; Kawai, R.; Tamazawa, K.; Takenaka, T.; Takahashi, K.; Murakami, M. Chem. Pharm. Bull. 1979, 27, 1426-1440.
http://dx.doi.org/10.1248/cpb.27.1426

[6]. Arrowsmith, J. E.; Campbell, S. F.; Cross, P. E.; Stubbs, J. K.; Burges, R. A.; Gardiner, D. G.; Blackburn, K. J. J. Med. Chem. 1986, 29, 1696-1702.
http://dx.doi.org/10.1021/jm00159a022

[7]. Goldmann, S.; Stoltefuss, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1559-1578.
http://dx.doi.org/10.1002/anie.199115591

[8]. Boer, R.; Gekeler, V. Drugs Future 1995, 20, 499-509.

[9]. Briukhanov, V. M.; Zverev-laf Elkin, V. I. Exp. Clin. Pharmacol. 1994, 57, 47-49.

[10]. Tusell, J. M.; Serratosa, S. J. Brain Res. 1993, 622, 99-104.
http://dx.doi.org/10.1016/0006-8993(93)90807-Y

[11]. Wachter, G. A.; Davis, M. C.; Martin, A. R.; Franzblau, S. G. J. Med. Chem. 1998, 41, 2436-2438.
http://dx.doi.org/10.1021/jm9708745

[12]. Desai, B.; Sureja, D.; Naliapara, Y.; Shah, A.; Saxena, A. K. Bioorg. Med. Chem. 2001, 9, 1993-1998.
http://dx.doi.org/10.1016/S0968-0896(01)00141-9

[13]. Sunkel, C. E.; de Casa-Juana, M. F.; Santos, L.; Gomez, M. M.; Villarroya, M.; Gonzalez-Morales, M. A.; Priego, J. G.; Ortega, M. P. J. Med. Chem. 1990, 33, 3205-3210.
http://dx.doi.org/10.1021/jm00174a017

[14]. Rafiee, E.; Eavani, S.; Rashidzadeh, S.; Joshaghani, M. Inorg. Chim. Acta 2009, 362, 3555-3562.
http://dx.doi.org/10.1016/j.ica.2009.03.049

[15]. Kumar, A.; Maurya, R. A. Tetrahedron2008, 64, 3477-3482.
http://dx.doi.org/10.1016/j.tet.2008.02.022

[16]. Davoodnia, A.; Khashi, M.; Niloofar, T. H. Chinese J. Catal. 2013, 34, 1173-1178.
http://dx.doi.org/10.1016/S1872-2067(12)60547-6

[17]. Ramchander, J.; Raju, G.; Rameshwar, N.; Reddy, T. S.; Reddy A. R. Spectrochimica Acta A 2012, 85, 210-216.
http://dx.doi.org/10.1016/j.saa.2011.09.062

[18]. Kar, P.; Mishra, B. G. Chem. Eng. J. 2013, 223, 647-656.
http://dx.doi.org/10.1016/j.cej.2013.03.050

[19]. Mirzaei, H.; Davoodnia, A. Chin. J. Catal. 2012, 33, 1502-1507.
http://dx.doi.org/10.1016/S1872-2067(11)60431-2

[20]. Safari, J.; Banitaba, S. H.; Khalil, S. D. Chin. J. Catal. 2011, 32, 1850-1854.
http://dx.doi.org/10.1016/S1872-2067(10)60295-1

[21]. Lee, Y. A.; Kim, S. C. J. Ind. Eng. Chem. 2011, 17, 401-403.
http://dx.doi.org/10.1016/j.jiec.2011.02.031

[22]. Chhillar, A. K.; Arya, P.; Mukherjee, C.; Kumar, P.; Yadav, Y.; Sharma, A. K.; Yadav, V.; Gupta, J.; Dabur, R.; Jha, H. N.; Watterson, A. C.; Parmar, V. S.; Prasadb, A. K.; Sharma, G. L. Bioorg. Med. Chem. 2006, 14, 973-981.
http://dx.doi.org/10.1016/j.bmc.2005.09.014

[23]. Kuraitheerthakumaran, A.; Pazhamalai, S.; Gopalakrishnan, M. Chinese Chem. Lett. 2011, 22, 1199-1202.

[24]. Kotharkar, S. A.; Shinde, D. B. Ukrainica Bioorg. Acta 2006, 1, 3-5.

[25]. Wang, S. X.; Li, Z. Y.; Zhang, j. C.; Li, J. T. Ultrason. Sonochem. 2008, 15, 677-680.
http://dx.doi.org/10.1016/j.ultsonch.2008.02.009

[26]. Wolfson, A.; Litvak, G.; Dlugy, C.; Shotland, Y.; Tavor, D. Ind. Crops. Prod. 2009, 30, 78-81.
http://dx.doi.org/10.1016/j.indcrop.2009.01.008

[27]. Wolfson, A.; Dlugy, C. Chem. Pap. 2007, 61, 228-232.
http://dx.doi.org/10.2478/s11696-007-0026-3

[28]. Wolfson, A.; Dlugy, C.; Shotland, Y. Environ. Chem. Lett. 2007, 5, 67-71.
http://dx.doi.org/10.1007/s10311-006-0080-z

[29]. Gu, Y.; Barrault, J.; Jerome, F. Adv. Synth. Catal. 2008, 350, 2007-2012.
http://dx.doi.org/10.1002/adsc.200800328

[30]. Karam, A.; Villandier, N.; Delample, M.; Koerkamp, C. K.; Douliez, J. P.; Granet, R.; Krausz, P.; Barrault, J.; Jerome, F. Chem. Eur. J. 2008, 14, 10196-10200.
http://dx.doi.org/10.1002/chem.200801495

[31]. He, F.; Li, P.; Gu, Y.; Li, G. Green Chem. 2009, 11, 1767-1773.
http://dx.doi.org/10.1039/b916015a

[32]. Radatz, C. S.; Silva, R. B.; Perin, G.; Lenardao, E. J.; Jacob, R. G.; Alves, D. Tetrahedron Lett. 2011, 52, 4132-4136.
http://dx.doi.org/10.1016/j.tetlet.2011.05.142

[33]. Nascimento, J. E. R.; Barcellos, A. M.; Sachini, M.; Perin, G.; Lenardao, E. J.; Alves, D.; Jacob, R. G.; Missau, F. Tetrahedron Lett. 2011, 52, 2571-2574.
http://dx.doi.org/10.1016/j.tetlet.2011.03.045

[34]. Tamaddon, F.; Razmi, Z.; Jafari, A. A. Tetrahedron Lett. 2010, 51, 1187-1189.
http://dx.doi.org/10.1016/j.tetlet.2009.12.098

[35]. Love, B.; Goodman, M. M.; Snader, K. M.; Tedeschi, R.; Macko, E. Eur. J. Med. Chem. 1974, 17, 956-965.
http://dx.doi.org/10.1021/jm00255a010

[36]. Leov, B.; Snader, K. M. J. Org. Chem. 1965, 30, 1914-1916.
http://dx.doi.org/10.1021/jo01017a048

[37]. Jacques, J.; Eynde, V.; Delfaese, F.; Mayence, A.; Haverbeke, Y. V. Tetrahedron 1995, 51, 6511-6516.
http://dx.doi.org/10.1016/0040-4020(95)00318-3

[38]. Ghosh, S.; Saikh, F.; Das, J.; Pramanik, A. K. Tetrahedron Lett. 2013, 54, 58-62.
http://dx.doi.org/10.1016/j.tetlet.2012.10.079

[39]. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G. Text book of Practical Organic Chemistry, 5thed., Longman Singapore, 1994.

[40]. Khadilkar, B. M.; Gaikar, V. G.; Chitnavis, A. A. Tetrahedron lett. 1995, 36, 8083-8086.
http://dx.doi.org/10.1016/0040-4039(95)01680-G

Most read articles by the same author(s)

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).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics