PEG-400: An efficient and recyclable reaction medium for the synthesis of pyrazolo[1,5-a]pyrimidines

Shankaraiah Guruvaiah Konda

doi:10.5155/eurjchem.5.4.676-680.1110

PDF

Published: Dec 31, 2014

DOI: https://doi.org/10.5155/eurjchem.5.4.676-680.1110

Keywords:

PEG-400, Recyclability, Benign synthesis, 5-Amino pyrazole, α, β-Unsaturated ketones, Pyrazolo[1, 5-a]pyrimidine

Section

Short Communication

Issue

Vol. 5 No. 4 (2014): December 2014

Dates

Received 2014-06-20
Accepted 2014-08-09
Published 2014-12-31

Shankaraiah Guruvaiah Konda

Department of Chemistry, Karamsibhai Jethabhai Somaiya College of Arts, Commerce and Science, Kopargaon, 423601, India

Abstract

An efficient and convenient route is described for the synthesis of new pyrazolo [1,5-a] pyrimidine derivatives by the reaction of 4-(4’-chloro-phenylazo)-5-amino pyrazole with α,β-unsaturated carbonyl compounds (chalcones) using polyethylene glycol (PEG-400) as benign reaction medium. The advantage of this protocol includes the excellent yields, operational simplicity, short reaction times and avoidance of volatile organic solvents and expensive catalysts.

This Abstract was viewed 1678 times |

Article PDF downloaded 839 times

How to Cite

(1)

Konda, S. G. PEG-400: An Efficient and Recyclable Reaction Medium for the Synthesis of pyrazolo[1,5-a]pyrimidines. Eur. J. Chem. 2014, 5, 676-680.

Links for Article

Crossref - Scopus - Google - European PMC

References

[1]. Novinson, T.; Bhooshan, B.; Okabe, T.; Revankar, G. R.; Wilson, H. R. J. Med. Chem. 1976, 19, 512-516.
http://dx.doi.org/10.1021/jm00226a013

[2]. Senga, K.; Novinson, T.; Wilson, H. R. J. Med. Chem. 1981, 24, 610-613.
http://dx.doi.org/10.1021/jm00137a023

[3]. Kirkpatrick, W. E.; Okabe, T.; Hillyard, W. I.; Robin, R. K.; Dren, A. T. J. Med. Chem. 1977, 20, 386-393.
http://dx.doi.org/10.1021/jm00213a014

[4] Selleri, S.; Bruni, F.; Costagli, C.; Costanzo, A.; Guerrini, G.; Ciciani, G.; Gratteri, P.; Besnard, F.; Costa, B.; Montali, M.; Martini, C.; Fohlin, J.; De Siena, G.; Malberg, P. J. Med. Chem. 2005, 48, 6756-6760.
http://dx.doi.org/10.1021/jm058002n

[5]. Suzuki, M.; Iwasaki, H.; Fujiwaki, Y.; Sakashita, M.; Kitahara, M.; Sakoda, R. Bioorg. Med. Chem. Lett. 2001, 11, 1285-1288.
http://dx.doi.org/10.1016/S0960-894X(01)00203-7

[6]. Almansa, C.; Arriba, A. F.; Cavalcanti, F. L.; Gomez, L.; Miralles, A.; Forn, J. J. Med. Chem. 2001, 44, 350-361.
http://dx.doi.org/10.1021/jm0009383

[7]. Fraley, M. E.; Rubino, R.; Hoffman, W. F.; Hambaugh, S. R.; Arrington, K. L.; Hungate, R. W.; Bilodeau, M. T.; Tebben, A. J.; Rutledge, R. Z.; McFall, R. C.; Huckle, W. R.; Kendall, R. L.; Coll, K. E.; Thomas, K. E. Bioorg. Med. Chem. Lett. 2002, 12, 3537-3541.
http://dx.doi.org/10.1016/S0960-894X(02)00827-2

[8]. Novinson, T.; Hanson, R.; Dimmitt, M. K.; Simmon, L. N.; Robins, R. K.; O'Brien, D. E. J. Med. Chem. 1974, 17, 645-648.
http://dx.doi.org/10.1021/jm00252a016

[9]. Selleri, S.; Bruni, F.; Costagli, C.; Costanzo, A.; Guerrini, G.; Ciciani, G.; Costa, B.; Mortini, C. Bioorg. Med. Chem. 2001, 9, 2661-2671.
http://dx.doi.org/10.1016/S0968-0896(01)00192-4

[10]. Lager, E.; Andersson, P.; Nilsson, J.; Pettersson, I.; Qstergaard, E.; Nielsen, M.; Sterner, O.; Liljefors, T. J. Med. Chem. 2006, 49, 2526-2533.
http://dx.doi.org/10.1021/jm058057p

[11]. Abu Elmaati, T.; El- Taweel, F. J. Heterocycl. Chem. 2004, 41, 109-134.
http://dx.doi.org/10.1002/jhet.5570410201

[12]. Dawane, B. S.; Konda S. G.; Zangade, S. B. J. Het. Chem. 2010, 47, 1250-1254.
http://dx.doi.org/10.1002/jhet.413

[13]. Fraley, M. F.; Hoffman, W. F.; Rubino, R.; Hungate, R. W.; Tebben, A. J.; Rutledge, R. Z.; McFall, R. C.; Huckle, W. R.; Kendall, R. L.; Coll, K. E.; Thomas, K. E. Bioorg. Med. Chem. Lett. 2002, 12, 2767-2770.
http://dx.doi.org/10.1016/S0960-894X(02)00525-5

[14]. Heldebrant, D.; Jessop, P. G. J. Am. Chem. Soc. 2003, 125, 5600-5601.
http://dx.doi.org/10.1021/ja029131l

[15]. Chandrasekhar, S.; Narsihmulu, Ch.; Sultana, S. S.; Reddy, N. R. K. Org. Lett. 2002, 4, 4383-4399.

[16]. Chandrasekhar, S.; Narsihmulu, Ch.; Sultana, S. S.; Reddy. N. R. K. Chem. Commun. 2003, 1716-1717.

[17]. Jiang, R.; Kuang, Y. –Q.; Sun, X. –L.; Zhang, S. Y. Tetrahedron: Asymmetry 2004, 15, 743-746.
http://dx.doi.org/10.1016/j.tetasy.2004.01.011

[18]. Namboodiri, V. V.; Varma, R. S. Green Chem. 2001, 3, 146-148.
http://dx.doi.org/10.1039/b102337n

[19]. Haimov, A.; Neumann, R. Chem. Commun. 2002, 876-877.
http://dx.doi.org/10.1039/b200559j

[20]. Konda, S. G.; Humne, V. T.; Lokhande, P. D. Green Chem. 2011, 13, 2354-2358.
http://dx.doi.org/10.1039/c1gc15153c

[21]. Chandrasekhar, S.; Narsihmulu, Ch.; Chandrashekar, G.; Shyamsunder T. Tetrahedron Lett. 2004, 45, 2421-2423.
http://dx.doi.org/10.1016/j.tetlet.2004.01.097

[22]. Perrier, S.; Gemici, H.; Li, S. Chem. Commun. 2004, 604-605.
http://dx.doi.org/10.1039/b313061d

[23]. Chen, J.; Spear, S. K.; Huddleston, J. G.; Rogers, R. D. Green Chem. 2005, 7, 64-82
http://dx.doi.org/10.1039/b413546f

[24]. Ballini, R.; Barboni, L.; Palmieri A. Green Chem. 2008, 10, 1004-1006.
http://dx.doi.org/10.1039/b805985c

[25]. Mallepalli, R.; Yeramanchi, L.; Bantu, R.; Nagarpu, L. Synlett, 2011, 2730-2732.

[26]. Huang, H.; Jiang, H.; Chen, K.; Liu, H. J. Org. Chem. 2009, 74, 5599-5602.
http://dx.doi.org/10.1021/jo9005206

[27]. Konda, S. G.; Shaikh, B. M.; Chavan, S. A.; Dawane, B. S. Chin. Chem. Lett. 2011, 22, 65-68.
http://dx.doi.org/10.1016/j.cclet.2010.09.012

[28]. Dawane, B. S.; Konda, S. G.; Mandawad, G. G.; Shaikh, B. M. Eur. J. Med. Chem. 2010, 45, 387-392.
http://dx.doi.org/10.1016/j.ejmech.2009.10.015

[29]. Dawane, B. S.; Konda S. G.; Bodadae, R. G.; Bhosale, R. B. J. Het. Chem. 2010, 47, 237-241.

[30]. Kamble, V. T.; Dawane, B. S.; Chavan, S. A.; Bhosale, R. B. Aust. J. Chem. 2007, 60, 302-304.
http://dx.doi.org/10.1071/CH06377

[31]. Dawane, B. S.; Konda, S. G.; Shaikh, B. M.; Bhosale, R. B. Acta Pharm. 2009, 59, 473-482.
http://dx.doi.org/10.2478/v10007-009-0034-7

[32]. Saleh, N. M.; Ammar, Y. A.; Micky, J. A.; Abbas, H. A. S.; EL-Gaby, M. S. A. Ind. J. Chem. 2004, 43(B), 2195-2202.

[33]. Krystof, V.; Canka, P.; Fryova, I.; Slouka, J.; Ge Kontopidis, Dzubak, P.; Hajduch, M.; Srovnal, J.; De Azevedo W. F.; Jr. Orsag . X. M.; Paprskarova, M.; Rolcık, J.; Ales Latr, Fischer, P. M.; Strnad, M. J. Med Chem. 2006, 49, 6500-6509.

[34]. Ammar, Y. A.; El-Sharief, A. M.; Zahran, M. A. Sh.; El-Said, M. Z.; El-Said, V. H. J. Chem. Res. (s) 1995, 324-325.

[35]. El- Gaby, M. S. A.; Sayed, A. Z.; Abu-Shanab, F. A.; Hessein, A. M. Phosphorus Sulfur 2000, 164, 1-10.

Supporting Agencies

University Grants Commission, New Delhi, Minor Research Project [F. No, 47-306/12(WRO)].

Most read articles by the same author(s)

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).

Article Sidebar

Main Article Content

Abstract

Article Details

Most read articles by the same author(s)

Downloads

Metrics