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

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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.

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(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.

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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)].

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