European Journal of Chemistry 2014, 5(4), 676-680 | doi: https://doi.org/10.5155/eurjchem.5.4.676-680.1110 | Get rights and content






  OPEN ACCESS | PEER-REVIEWED | SHORT COMMUNICATION | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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 | Revised: 02 Aug 2014 | Accepted: 09 Aug 2014 | Published: 31 Dec 2014 | Issue Date: December 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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.5.4.676-680.1110

Links for Article


| | | | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 797 times | PDF Article downloaded 272 times

Funding information


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

Citations

/


[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
/


[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
/


[3]. Joana F. Campos, Sabine Berteina-Raboin
Greener Synthesis of Nitrogen-Containing Heterocycles in Water, PEG, and Bio-Based Solvents
Catalysts  10(4), 429, 2020
DOI: 10.3390/catal10040429
/


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. 24 Oct. 2020
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)

The other citation formats (EndNote | Reference Manager | ProCite | BibTeX | RefWorks) for this article can be found online at: How to cite item


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

| | | | | | |

| | | | | |

Save to Zotero Save to Mendeley



European Journal of Chemistry 2014, 5(4), 676-680 | doi: https://doi.org/10.5155/eurjchem.5.4.676-680.1110 | Get rights and content

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2010 - 2020  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2010-2020 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 2850 Smith Ridge Trce Peachtree Cor GA 30071-2636, USA. Registered in USA.