Glycerol mediated, one pot, multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles

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

doi:10.5155/eurjchem.4.4.450-453.769

PDF

Published: Dec 31, 2013

DOI: https://doi.org/10.5155/eurjchem.4.4.450-453.769

Keywords:

Glycerol, Aldehydes, Catalyst free, Malononitrile, Pyrazol-5-one, Dihydropyrano[2, 3-c]pyrazole

Section

Research Article

Issue

Vol. 4 No. 4 (2013): December 2013

Dates

Received 2013-03-12
Accepted 2013-06-14
Published 2013-12-31

Harvinder Singh Sohal

Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India

Arun Goyal

Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India

Rajeev Sharma

Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India

Rajshree Khare

Department of Chemistry, Maharishi Markandeshwar University, Mullana, 133207, Haryana, India

Sanjay Kumar

Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India

Abstract

Multi component, one pot synthesis of various dihydropyrano[2,3-c]pyrazole derivatives from the condensation of ethyl acetoacetate, hydrazine, aromatic aldehyde and malononitrile has been described using glycerol, as environmentally benign, economical, and easily available solvent. The targeted molecules are obtained in excellent yield without use of any additional catalyst.

This Abstract was viewed 2283 times |

Article PDF downloaded 1408 times

How to Cite

(1)

Sohal, H. S.; Goyal, A.; Sharma, R.; Khare, R.; Kumar, S. Glycerol Mediated, One Pot, Multicomponent Synthesis of dihydropyrano[2,3-c]pyrazoles. Eur. J. Chem. 2013, 4, 450-453.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Handy, S. T. Chem. Eur. J. 2003, 9, 2938-2944.
http://dx.doi.org/10.1002/chem.200304799

[2]. Leitner, W. Green Chem. 2007, 9, 923-923.
http://dx.doi.org/10.1039/b712156n

[3]. Horváth, I. T. Green Chem. 2008, 10, 1024-1028.
http://dx.doi.org/10.1039/b812804a

[4]. Giovanni, I.; Silke, H.; Dieter, L.; Burkhard, K. Green Chem. 2006, 8, 1051-1055.
http://dx.doi.org/10.1039/b603660k

[5]. Clark, J. H. Green Chem. 1999, 1, 1-8.
http://dx.doi.org/10.1039/a807961g

[6]. Simon, M. O.; Li, C. J. Chem. Soc. Rev. 2012, 41, 1415-1427.
http://dx.doi.org/10.1039/c1cs15222j
PMid:22048162

[7]. Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302-6337.
http://dx.doi.org/10.1021/cr100162c
PMid:20815348

[8]. Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725-748.
http://dx.doi.org/10.1021/cr800448q
PMid:19209944

[9]. Li, C. J. Chem. Rev. 2007, 107, 2546-2562.
http://dx.doi.org/10.1021/cr050009p

[10]. Li, C. J. Chem. Rev. 2005, 105, 3095-3166.
http://dx.doi.org/10.1021/cr030009u
PMid:16092827

[11]. Li, C. J. Chem. Rev. 1993, 93, 2023-2035.
http://dx.doi.org/10.1021/cr00022a004

[12]. Pagliaro, M.; Rossi, M. The Future of Glycerol: New Usages for a Versatile Raw Material; Clark, J. H.; Kraus, G. A. Eds.; RSC Green Chemistry Series: Cambridge, 2008.

[13]. Pagliaro, M.; Ciriminna, R.; Kimura, H.; Rossi M.; Pina, C. D. Angew. Chem. Int. Ed. 2007, 46, 4434-4440.
http://dx.doi.org/10.1002/anie.200604694
PMid:17471485

[14]. Corma, A.; Iborra S.; Velty, A. Chem. Rev. 2007, 107, 2411-2502.
http://dx.doi.org/10.1021/cr050989d
PMid:17535020

[15]. Armaroli, N.; Balzani, V. Angew. Chem. Int. Ed. 2007, 46, 52-66.
http://dx.doi.org/10.1002/anie.200602373
PMid:17103469

[16]. Jerome, F.; Pouilloux, Y.; Barrault, J. ChemSusChem. 2008, 1, 586-613.
http://dx.doi.org/10.1002/cssc.200800069
PMid:18702160

[17]. Zhou, C. H.; Beltramini, J. N.; Fan, Y. X.; Lu, G. Q. Chem. Soc. Rev. 2008, 37, 527-549.
http://dx.doi.org/10.1039/b707343g
PMid:18224262

[18]. Behr, A.; Eilting, J.; Irawadi, K.; Leschinski, J.; Lindner, F. Green Chem. 2008, 10, 13-30.
http://dx.doi.org/10.1039/b710561d

[19]. Bachhav, H. M.; Bhagat, S. B.; Telvekar, V. N. Tetrahedron Lett. 2011, 52, 5697-5701.
http://dx.doi.org/10.1016/j.tetlet.2011.08.105

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

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

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

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

[24]. 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
PMid:18855952

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

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

[27]. Nascimento, J. E. R.; Barcellos, A. M.; Sachini, M.; Perin, G.; Lenardão, 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

[28]. Junek, H.; Aigner, H. Chem. Ber. 1973, 106, 914-921.
http://dx.doi.org/10.1002/cber.19731060323

[29]. Wamhoff, H.; Kroth, E.; Strauch, K. Synthesis 1993, 11, 1129-1132.
http://dx.doi.org/10.1055/s-1993-26014

[30]. Tacconi, G.; Gatti, G.; Desimoni, G. J. Prakt. Chem. 1980, 322, 831-834.
http://dx.doi.org/10.1002/prac.19803220519

[31]. Sharanin Yu, A.; Sharanina, L. G.; Puzanova, V. V. Zh. Org. Khim. 1983, 19, 2609-2615.

[32]. El-Tamany, E. S.; El-Shahed, F. A.; Mohamed, B. H. J. Serb. Chem. Soc. 1999, 64, 9-18.

[33]. Ismail, Z. H.; Aly, G. M.; El-Degwi, M. S.; Heiba, H. I.; Ghorab, M. M. Egypt J. Biotechnol. 2003, 13, 73-82.

[34]. Zaki, M. E. A.; Soliman, H. A.; Hiekal, O. A.; Rashad, A. E. Z. Naturforsc. 2006, 61, 1-5.

[35]. Abdelrazek, F. M.; Metz, P.; Metwally, N. H.; El-Mahrouky, S. F. Arch. Pharm. 2006, 339, 456-460.
http://dx.doi.org/10.1002/ardp.200600057
PMid:16795107

[36]. Abdelrazek, F. M.; Metz, P.; Kataeva, O.; Jaeger, A.; El-Mahrouky, S. F. Arch. Pharm. 2007, 340, 543-548.
http://dx.doi.org/10.1002/ardp.200700157
PMid:17912679

[37]. Foloppe, N.; Fisher, L. M.; Howes, R.; Potter, A.; Robertson, A. G. S.; Surgenor, A. E. Bioorg. Med. Chem. 2006, 14, 4792-4802.
http://dx.doi.org/10.1016/j.bmc.2006.03.021
PMid:16574416

[38]. Kimata, A.; Nakagawa, H.; Ohyama, R.; Fukuuchi, T.; Ohta, S.; Suzuki, T.; Miyata, N. J. Med. Chem. 2007, 50, 5053-5056.
http://dx.doi.org/10.1021/jm070688r
PMid:17850126

[39]. Armetso, D.; Horspool, W. M.; Martin, N.; Ramos, A.; Seaone, C. J. Org. Chem. 1989, 54, 3069-3072.
http://dx.doi.org/10.1021/jo00274a021

[40]. Jin, T. S.; Zhao, R. Q.; Li, T. S. Arkivoc 2006, 11, 176-182.
http://dx.doi.org/10.3998/ark.5550190.0007.b18

[41]. Babaie, M.; Sheibani, H. Arab. J. Chem. 2011, 4, 159-162.
http://dx.doi.org/10.1016/j.arabjc.2010.06.032

[42]. Siddekha, A.; Nizam, A.; Pasha, M. A. Spectrochim. Acta A 2011, 81, 431-440.
http://dx.doi.org/10.1016/j.saa.2011.06.033
PMid:21795106

[43]. Vasuki, G.; Kandhasamy, K. Tetrahedron Lett. 2008, 49, 5636-5638.
http://dx.doi.org/10.1016/j.tetlet.2008.07.055

[44]. Hamood, S.; Azzam, S.; Pasha, M. A. Tetrahedron Lett. 2012, 50, 6834-6837.

Supporting Agencies

University Grants Commission (Sanction No. F.No.8-2 (52)/2011 (MRP/NCRB)), New Delhi, India

Most read articles by the same author(s)

Harvinder Singh Sohal, 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: Vol. 5 No. 1 (2014): March 2014
Salman Ahmad Khan, Abdullah Mohamed Asiri, Sanjay Kumar, Kamlesh Sharma, Green synthesis, antibacterial activity and computational study of pyrazoline and pyrimidine derivatives from 3-(3,4-dimethoxy-phenyl-1-(2,5-dimethyl-thiophen-3-yl)-propenone , European Journal of Chemistry: Vol. 5 No. 1 (2014): March 2014
Harvinder Singh Sohal, Arun Goyal, Rajshree Khare, Kishanpal Singh, Rajeev Sharma, Catalyst free, one-pot, facile synthesis of novel pyrazolo-1,4-dihydropyridine derivative form pyranopyrazoles , European Journal of Chemistry: Vol. 5 No. 2 (2014): June 2014

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).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics