European Journal of Chemistry 2013, 4(4), 450-453 | doi: https://doi.org/10.5155/eurjchem.4.4.450-453.769 | Get rights and content






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


Harvinder Singh Sohal (1) , Arun Goyal (2) , Rajeev Sharma (3) , Rajshree Khare (4) , Sanjay Kumar (5,*)

(1) Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India
(2) Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India
(3) Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India
(4) Department of Chemistry, Maharishi Markandeshwar University, Mullana, 133207, Haryana, India
(5) Department of Chemistry, Multani Mal Modi College, Patiala, 147001, Punjab, India
(*) Corresponding Author

Received: 12 Mar 2013 | Revised: 13 Jun 2013 | Accepted: 14 Jun 2013 | Published: 31 Dec 2013 | Issue Date: December 2013

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.

4_4_450_453

Keywords


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

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DOI: 10.5155/eurjchem.4.4.450-453.769

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Funding information


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

Citations

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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.

How to cite


Sohal, H.; Goyal, A.; Sharma, R.; Khare, R.; Kumar, S. Eur. J. Chem. 2013, 4(4), 450-453. doi:10.5155/eurjchem.4.4.450-453.769
Sohal, H.; 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(4), 450-453. doi:10.5155/eurjchem.4.4.450-453.769
Sohal, H., Goyal, A., Sharma, R., Khare, R., & Kumar, S. (2013). Glycerol mediated, one pot, multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles. European Journal of Chemistry, 4(4), 450-453. doi:10.5155/eurjchem.4.4.450-453.769
Sohal, Harvinder, Arun Goyal, Rajeev Sharma, Rajshree Khare, & Sanjay Kumar. "Glycerol mediated, one pot, multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles." European Journal of Chemistry [Online], 4.4 (2013): 450-453. Web. 28 Nov. 2020
Sohal, Harvinder, Goyal, Arun, Sharma, Rajeev, Khare, Rajshree, AND Kumar, Sanjay. "Glycerol mediated, one pot, multicomponent synthesis of dihydropyrano[2,3-c]pyrazoles" European Journal of Chemistry [Online], Volume 4 Number 4 (31 December 2013)

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

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