European Journal of Chemistry 2014, 5(4), 676-680. doi:10.5155/eurjchem.5.4.676-680.1110

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


Shankaraiah Guruvaiah Konda (1,*)

(1) Department of Chemistry, Karamsibhai Jethabhai Somaiya College of Arts, Commerce and Science, Kopargaon, 423601, India
(*) Corresponding Author

Received: 20 Jun 2014, Accepted: 09 Aug 2014, Published: 31 Dec 2014

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.


Keywords


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

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DOI: 10.5155/eurjchem.5.4.676-680.1110

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Citations

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[1]. Douaa Salman AlMarzouq, Omniya Sayed Zaky, Abdulaziz Abdulrazaq AlNajjar, Kamal Usef Sadek
Pressure as effective green technology for synthesis of polyfunctionally substituted heteroaromatics: Synthesis of a variety of pyrazolo[1,5-a]pyrimidines
European Journal of Chemistry  7(3), 347, 2016
DOI: 10.5155/eurjchem.7.3.347-351.1473
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[2]. Mohammed Loubidi, Catherine Manga, Zahira Tber, Ibtissam Bassoude, El Mokhtar Essassi, Sabine Berteina-Raboin
One-Pot SN Ar/Direct Pd-Catalyzed CH Arylation Functionalization of Pyrazolo[1,5-a ]pyrimidine at the C3 and C7 Positions
European Journal of Organic Chemistry  2018(29), 3936, 2018
DOI: 10.1002/ejoc.201800580
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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.


How to cite


Konda, S. Eur. J. Chem. 2014, 5(4), 676-680. doi:10.5155/eurjchem.5.4.676-680.1110
Konda, S. PEG-400: An efficient and recyclable reaction medium for the synthesis of pyrazolo[1,5-a]pyrimidines. Eur. J. Chem. 2014, 5(4), 676-680. doi:10.5155/eurjchem.5.4.676-680.1110
Konda, S. (2014). PEG-400: An efficient and recyclable reaction medium for the synthesis of pyrazolo[1,5-a]pyrimidines. European Journal of Chemistry, 5(4), 676-680. doi:10.5155/eurjchem.5.4.676-680.1110
Konda, Shankaraiah. "PEG-400: An efficient and recyclable reaction medium for the synthesis of pyrazolo[1,5-a]pyrimidines." European Journal of Chemistry [Online], 5.4 (2014): 676-680. Web. 14 Nov. 2019
Konda, Shankaraiah. "PEG-400: An efficient and recyclable reaction medium for the synthesis of pyrazolo[1,5-a]pyrimidines" European Journal of Chemistry [Online], Volume 5 Number 4 (31 December 2014)

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

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