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

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Published: Mar 31, 2016
DOI: https://doi.org/10.5155/eurjchem.7.1.107-114.1369
Keywords:
Amidines, Heterocycles, Electrophiles, Aminopyrazoles, Pyrazolotriazines, Pyrazolopyrimidines
Section
Research Article
Issue
Vol. 7 No. 1 (2016): March 2016
Dates
Received 2015-11-18
Accepted 2016-01-01
Published 2016-03-31


Main Article Content

Husien Hasan Abbas-Temirek
Chemistry Department, Faculty of Science, South Valley University, Qena, 83523 Egypt
Ahmed Mohammed Abo-Bakr
Chemistry Department, Faculty of Science, South Valley University, Qena, 83523 Egypt

Abstract

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.


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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.

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References

[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.
http://dx.doi.org/10.1590/S0103-50532009000200003

[2]. Ghozlan, S. A. S.; Abdelrazek, F. M.; Mona, H. M.; Khaled, E. A. J. Heterocyclic. Chem. 2010, 47, 1379-1385.
http://dx.doi.org/10.1002/jhet.482

[3]. Liekens, S.; Bronckaers, A.; Balzarini, J. Lancet Oncol. 2009, 10(6), 628-635.
http://dx.doi.org/10.1016/S1470-2045(09)70037-3

[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.
http://dx.doi.org/10.1021/jm00226a013

[5]. Asem, S. D.; Shunan, K.; Jai, N. V. J. Mol. Divers. 2015, 19(4), 759-771.
http://dx.doi.org/10.1007/s11030-015-9606-2

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

[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.
http://dx.doi.org/10.1016/j.ejmech.2013.04.029

[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.
http://dx.doi.org/10.1016/j.bmc.2008.06.054

[10]. Refaee, M.; Ahmed, K. E.; Mahmoud, F. I.; Sayed, A. S. Eur. J. Chem. 2011, 2(3), 347-355.
http://dx.doi.org/10.5155/eurjchem.2.3.347-355.168

[11]. Charles, Q. H.; Keith, M. W.; Dimitri, E. G.; James, R. M.; Chen, C. Bioorg. Med. Chem. Lett. 2004, 14(15), 3943-3947.
http://dx.doi.org/10.1016/j.bmcl.2004.05.056

[12]. Suzuki, M.; Iwasaki, H.; Fujikawa, 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

[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.
http://dx.doi.org/10.1021/jm0009383

[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.
http://dx.doi.org/10.1016/S0960-894X(02)00525-5

[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.
http://dx.doi.org/10.1016/S0960-894X(02)00827-2

[16]. Hantzsch, A.; Wolvekamp, M. Justus liebigs Ann. Chem. 1904, 331, 265-297.
http://dx.doi.org/10.1002/jlac.19043310302

[17]. Gompper, R.; Gang, M.; Saygin, F. Tetrahedron Lett. 1966, 7(17), 1885-1889.
http://dx.doi.org/10.1016/S0040-4039(00)90276-4

[18]. Erra-Balsells, R.; Frasca, A. R. Austr. J. Chem 1988, 41(1), 103-110.
http://dx.doi.org/10.1071/CH9880103

[19]. Biondic, M. C.; Erra-Balsells, R. J. Photochem. Photobiol. , Sec. A Chem. 1990, 51, 341-353.
http://dx.doi.org/10.1016/1010-6030(90)87068-M

[20]. Tominaga, Y.; Ohno, S.; Fujito, H.; Mazume, H. J. Heterocyclic. Chem. 1991, 28, 1039-1042.
http://dx.doi.org/10.1002/jhet.5570280434

[21]. Sadek, K. U.; Selim, N. A.; Elnagdi, M. H.; Otto, H. H. Bull. Chem. Soc. Jpn. 1993, 66, 2927-2930.
http://dx.doi.org/10.1246/bcsj.66.2927

[22]. Ibrahim, N. S.; Sadek, K. U.; Abdel-Al, F. A. Arch. Pharm. (Weinheim) 1987, 320, 240-246.
http://dx.doi.org/10.1002/ardp.19873200310

[23]. Hassanien, A. A.; Amrb, A. E.; Ghozlan, S. A. S. J. Chin. Chem. Soc. 2000, 47 (6), 1273-1278.
http://dx.doi.org/10.1002/jccs.200000176

[24]. Dieler, R. K. Tetrahedron 1986, 42(12), 3029-3096.
http://dx.doi.org/10.1016/S0040-4020(01)87376-2

[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.
http://dx.doi.org/10.1007/BF00898055

[27]. Reimlinger, H.; VanOverstaeten, A. Chem. Ber. 1961, 94(4), 1036-1041.
http://dx.doi.org/10.1002/cber.19610940420

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South Valley University, Qena, 83523 Egypt
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