European Journal of Chemistry 2014, 5(1), 171-175 | doi: https://doi.org/10.5155/eurjchem.5.1.171-175.943 | Get rights and content

Issue cover





  Open Access OPEN ACCESS | Open Access PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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


Harvinder Singh Sohal (1,*) , Arun Goyal (2) , Rajeev Sharma (3) , Rajshree Khare (4)

(1) Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India
(2) Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India
(3) Department of Chemistry, Multani Mal Modi College, Patiala-147 001, Punjab, India
(4) Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India
(*) Corresponding Author

Received: 05 Oct 2013 | Revised: 21 Nov 2013 | Accepted: 27 Nov 2013 | Published: 31 Mar 2014 | Issue Date: March 2014

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.


Announcements


Our editors have decided to support scientists to publish their manuscripts in European Journal of Chemistry without any financial constraints.

1- The article processing fee will not be charged from the articles containing the single-crystal structure characterization between July 1, 2022 and August 15, 2022 (Voucher code: SINGLE2022).

2. Young writers will not be charged for the article processing fee between July 1, 2022 and August 15, 2022 (Voucher code: YOUNG2022).

3. The article processing fee will not be charged from the articles containing a part of the PhD thesis between July 1, 2022 and August 15, 2022 (Voucher code: PhD2022).

Editor-in-Chief

European Journal of Chemistry

Keywords


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

Full Text:

PDF
PDF    Open Access

DOI: 10.5155/eurjchem.5.1.171-175.943

Links for Article


| | | | | | |

| | | | | | |

| | | |

Related Articles




Article Metrics

icon graph This Abstract was viewed 3841 times | icon graph PDF Article downloaded 812 times

Funding information


Maharishi Markandeshwar University, Mullana, Ambala, India

Citations

/


[1]. J. Ashwin Kumar, Gomathi Shridhar, Savita Ladage, Lakshmy Ravishankar
Synthesis of 1,4-dihydropyridine esters using low-melting sugar mixtures as green solvents
Synthetic Communications  46(24), 1989, 2016
DOI: 10.1080/00397911.2016.1242750
/


[2]. Diego da Costa Cabrera, Eduarda Santa-Helena, Heloisa P. Leal, Renata Rodrigues de Moura, Luiz Eduardo Maia Nery, Carla Amorim Neves Gonçalves, Dennis Russowsky, Marcelo G. Montes D'Oca
Synthesis and antioxidant activity of new lipophilic dihydropyridines
Bioorganic Chemistry  84, 1, 2019
DOI: 10.1016/j.bioorg.2018.11.009
/


[3]. Dharambeer S. Malhi, Manvinder Kaur, Harvinder S. Sohal
Effect of Substitutions on 1, 4‐Dihdropyridines to Achieve Potential Anti‐Microbial Drugs: A Review
ChemistrySelect  4(38), 11321, 2019
DOI: 10.1002/slct.201902354
/


[4]. Amna M. Abdella, Amr M. Abdelmoniem, Ismail A. Abdelhamid, Ahmed H. M. Elwahy
Synthesis of heterocyclic compounds via Michael and Hantzsch reactions
Journal of Heterocyclic Chemistry  57(4), 1476, 2020
DOI: 10.1002/jhet.3883
/


[5]. Dharambeer S. Malhi, Harvinder S. Sohal, Kishanpal Singh, Zainab M. Almarhoon, Abir Ben Bacha, Maha I. Al-Zaben
Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity
ACS Omega  7(18), 16055, 2022
DOI: 10.1021/acsomega.2c01316
/


[6]. Mohamed Abd-Elmonem, Ramadan A. Mekheimer, Alaa M. Hayallah, Fatma A. Abo Elsoud, Kamal U. Sadek
Recent Advances in the Utility of Glycerol as a Benign and Biodegradable Medium in Heterocyclic Synthesis
Current Organic Chemistry  23(28), 3226, 2020
DOI: 10.2174/1385272823666191025150646
/


[7]. Rakesh Kumar, Neha Yadav, Rodolfo Lavilla, Daniel Blasi, Jordi Quintana, José Manuel Brea, María Isabel Loza, Jordi Mestres, Mamta Bhandari, Ritu Arora, Rita Kakkar, Ashok K. Prasad
Synthesis, pharmacological evaluation and molecular docking of pyranopyrazole-linked 1,4-dihydropyridines as potent positive inotropes
Molecular Diversity  21(3), 533, 2017
DOI: 10.1007/s11030-017-9738-7
/


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


How to cite


Sohal, H.; Goyal, A.; Sharma, R.; Khare, R. Eur. J. Chem. 2014, 5(1), 171-175. doi:10.5155/eurjchem.5.1.171-175.943
Sohal, H.; 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(1), 171-175. doi:10.5155/eurjchem.5.1.171-175.943
Sohal, H., Goyal, A., Sharma, R., & Khare, R. (2014). One-pot, multicomponent synthesis of symmetrical Hantzsch 1,4-dihydropyridine derivatives using glycerol as clean and green solvent. European Journal of Chemistry, 5(1), 171-175. doi:10.5155/eurjchem.5.1.171-175.943
Sohal, Harvinder, Arun Goyal, Rajeev Sharma, & Rajshree Khare. "One-pot, multicomponent synthesis of symmetrical Hantzsch 1,4-dihydropyridine derivatives using glycerol as clean and green solvent." European Journal of Chemistry [Online], 5.1 (2014): 171-175. Web. 6 Jul. 2022
Sohal, Harvinder, Goyal, Arun, Sharma, Rajeev, AND Khare, Rajshree. "One-pot, multicomponent synthesis of symmetrical Hantzsch 1,4-dihydropyridine derivatives using glycerol as clean and green solvent" European Journal of Chemistry [Online], Volume 5 Number 1 (31 March 2014)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item



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

CrossRef | Scilit | GrowKudos | Researchgate | Publons | ScienceGate | scibey | Scite | Lens | OUCI

WorldCat Paperbuzz | LibKey Citeas | Dimensions | Semanticscholar | Plumx | Kopernio | Zotero | Mendeley

ZoteroSave to Zotero MendeleySave to Mendeley



European Journal of Chemistry 2014, 5(1), 171-175 | doi: https://doi.org/10.5155/eurjchem.5.1.171-175.943 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)





© Copyright 2010 - 2022  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 2010-2022 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.