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

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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.

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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.

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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.

Supporting Agencies

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

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