European Journal of Chemistry

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



Main Article Content

Harvinder Singh Sohal
Arun Goyal
Rajeev Sharma
Rajshree Khare
Sanjay Kumar

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

icon graph This Abstract was viewed 2153 times | icon graph Article PDF downloaded 1334 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.

Article Details

Share
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
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 © 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).