European Journal of Chemistry

Reactions with heterocyclic amidines: Synthesis of several new pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a][1,3,5]triazines

Main Article Content

Husien Hasan Abbas-Temirek
Ahmed Mohammed Abo-Bakr


N-Bis(methylthio)methylenecyanamide (1) was allowed to react with ethylcyanoacetate or malononitrile in the presence of potassium carbonate in dimethylsulfoxide to yield the urea derivatives (3a,b), which on treatment with hydrazine hydrater resulted the corresponding aminopyrazole derivatives (4a,b). The cyclic amidine 5-amino-3-ureido-1H-pyrazole-4-carboxylic acid ethyl ester (4a) is found to be useful intermediate for the synthesis of new pyrazolopyrimidine and pyrazolotriazine derivatives (5-22a,b). The chemical structures of the synthesized compounds (3a,b-22a,b) were characterized by their elemental analyses, FT-IR, 1H 13C NMR and mass spectra.

icon graph This Abstract was viewed 1950 times | icon graph Article PDF downloaded 805 times

How to Cite
Abbas-Temirek, H. H.; Abo-Bakr, A. M. Reactions With Heterocyclic Amidines: Synthesis of Several New pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a][1,3,5]triazines. Eur. J. Chem. 2016, 7, 107-114.

Article Details

Crossref - Scopus - Google - European PMC

[1]. Marcos, P. M.; Elisandra, S.; Clarissa, P. F.; Fernanda, A. R.; Helio, G. B.; Nilo, Z. J. Braz. Chem. Soc. 2009, 20(2), 205-213.

[2]. Ghozlan, S. A. S.; Abdelrazek, F. M.; Mona, H. M.; Khaled, E. A. J. Heterocyclic. Chem. 2010, 47, 1379-1385.

[3]. Liekens, S.; Bronckaers, A.; Balzarini, J. Lancet Oncol. 2009, 10(6), 628-635.

[4]. Novinson, T.; Bhooshan, B.; Okabe, T.; Revankar, G. R.; Wilson, H. R.; Robins, R. K.; Senga, K. J. Med. Chem. 1976, 19, 512-516.

[5]. Asem, S. D.; Shunan, K.; Jai, N. V. J. Mol. Divers. 2015, 19(4), 759-771.

[6]. Senga, K.; Novinson, T.; Wilson, H. R.; Robins, R. K. J. Med. Chem. 1981, 24, 610-613.

[7]. Wedad, M. A.; Tahir, M. I. M.; Siti-Noor-Adnalizawati, A.; Siti-Farah, H.; Nazlina, I.; Yaacob, W. A. Eur. J. Med. Chem. 2013, 64, 464-476.

[8]. Essam, A.; Said, A. S.; Assy, M. G.; Atef, M. A. Am. J. Org. Chem. 2013, 3(1), 16-23.

[9]. Aymn, E. R.; Mohamed, I. H.; Randa, E. A.; Jehan, A. M. Bioorgan. Med. Chem. 2008, 16(15), 7102-7106.

[10]. Refaee, M.; Ahmed, K. E.; Mahmoud, F. I.; Sayed, A. S. Eur. J. Chem. 2011, 2(3), 347-355.

[11]. Charles, Q. H.; Keith, M. W.; Dimitri, E. G.; James, R. M.; Chen, C. Bioorg. Med. Chem. Lett. 2004, 14(15), 3943-3947.

[12]. Suzuki, M.; Iwasaki, H.; Fujikawa, Y.; Sakashita, M.; Kitahara, M.; Sakoda, R. Bioorg. Med. Chem. Lett. 2001, 11, 1285-1288.

[13]. Almansa, C.; Merlos, M.; Rafanell, J. G.; Arriba, A. F.; Cavalcanti, F. I.; Gomez, I. A.; Miralles, A. J. Med. Chem. 2001, 44, 350-361.

[14]. Fraley, M. E.; Hoffman, W. F.; Rubino, R. S.; Hungate, R. W.; Tebben, A. J.; Rutledge, R. Z.; Mcfall, R. C.; Huckle, W. R.; Kendall, R. I.; Coll, K. E.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2002, 12(19), 2767-2770.

[15]. Mark, E. F.; William, F. H.; Robert, S. R.; Randall, W. H.; Andrew, J. T.; Ruth, Z. R.; Rosemary, C. M.; William, R. H.; Richard, L. K.; Kathleen, E. C.; Kenneth, A. T. Bioorg. Med. Chem. Lett. 2002, 12, 3537-3541.

[16]. Hantzsch, A.; Wolvekamp, M. Justus liebigs Ann. Chem. 1904, 331, 265-297.

[17]. Gompper, R.; Gang, M.; Saygin, F. Tetrahedron Lett. 1966, 7(17), 1885-1889.

[18]. Erra-Balsells, R.; Frasca, A. R. Austr. J. Chem 1988, 41(1), 103-110.

[19]. Biondic, M. C.; Erra-Balsells, R. J. Photochem. Photobiol. , Sec. A Chem. 1990, 51, 341-353.

[20]. Tominaga, Y.; Ohno, S.; Fujito, H.; Mazume, H. J. Heterocyclic. Chem. 1991, 28, 1039-1042.

[21]. Sadek, K. U.; Selim, N. A.; Elnagdi, M. H.; Otto, H. H. Bull. Chem. Soc. Jpn. 1993, 66, 2927-2930.

[22]. Ibrahim, N. S.; Sadek, K. U.; Abdel-Al, F. A. Arch. Pharm. (Weinheim) 1987, 320, 240-246.

[23]. Hassanien, A. A.; Amrb, A. E.; Ghozlan, S. A. S. J. Chin. Chem. Soc. 2000, 47 (6), 1273-1278.

[24]. Dieler, R. K. Tetrahedron 1986, 42(12), 3029-3096.

[25]. Elgemeie, G. H.; Elghandour, A. H.; Elzanate, A. M.; Ahmed, S. A. J. Chem. Soc., Perkin Trans. I 1997, 21, 3285-3289.

[26]. Schmidt, H. W.; Junek, H. Monatsh. Chem. 1977, 108(4), 895-900.

[27]. Reimlinger, H.; VanOverstaeten, A. Chem. Ber. 1961, 94(4), 1036-1041.

Supporting Agencies

South Valley University, Qena, 83523 Egypt
Most read articles by the same author(s)

Dimensions - Altmetric - scite_ - PlumX

Downloads and views


Download data is not yet available.


Metrics Loading ...
License Terms

License Terms


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 and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License ( 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 ( are administered by Atlanta Publishing House LLC (European Journal of Chemistry).