European Journal of Chemistry 2016, 7(1), 107-114 | doi: https://doi.org/10.5155/eurjchem.7.1.107-114.1369 | Get rights and content

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


Husien Hasan Abbas-Temirek (1) , Ahmed Mohammed Abo-Bakr (2,*)

(1) Chemistry Department, Faculty of Science, South Valley University, Qena, 83523 Egypt
(2) Chemistry Department, Faculty of Science, South Valley University, Qena, 83523 Egypt
(*) Corresponding Author

Received: 18 Nov 2015 | Revised: 27 Dec 2015 | Accepted: 01 Jan 2016 | Published: 31 Mar 2016 | Issue Date: March 2016

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.


Keywords


Amidines; Heterocycles; Electrophiles; Aminopyrazoles; Pyrazolotriazines; Pyrazolopyrimidines

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DOI: 10.5155/eurjchem.7.1.107-114.1369

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Funding information


South Valley University, Qena, 83523 Egypt

Citations

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[1]. Amal Al-Azmi
Pyrazolo[1,5-a]pyrimidines: A Close Look into their Synthesis and Applications
Current Organic Chemistry  23(6), 721, 2019
DOI: 10.2174/1385272823666190410145238
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[2]. Ranjana Aggarwal, Suresh Kumar
5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines
Beilstein Journal of Organic Chemistry  14, 203, 2018
DOI: 10.3762/bjoc.14.15
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[3]. Mohamed A. Salem, Mohamed H. Helal, Moustafa A. Gouda, Hala H. Abd EL-Gawad, Marwa A. M. Shehab, Abeer El-Khalafawy
Recent synthetic methodologies for pyrazolo[1,5-a]pyrimidine
Synthetic Communications  49(14), 1750, 2019
DOI: 10.1080/00397911.2019.1604967
/


[4]. 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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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


How to cite


Abbas-Temirek, H.; Abo-Bakr, A. Eur. J. Chem. 2016, 7(1), 107-114. doi:10.5155/eurjchem.7.1.107-114.1369
Abbas-Temirek, H.; Abo-Bakr, A. 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(1), 107-114. doi:10.5155/eurjchem.7.1.107-114.1369
Abbas-Temirek, H., & Abo-Bakr, A. (2016). Reactions with heterocyclic amidines: Synthesis of several new pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a][1,3,5]triazines. European Journal of Chemistry, 7(1), 107-114. doi:10.5155/eurjchem.7.1.107-114.1369
Abbas-Temirek, Husien, & Ahmed Mohammed Abo-Bakr. "Reactions with heterocyclic amidines: Synthesis of several new pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a][1,3,5]triazines." European Journal of Chemistry [Online], 7.1 (2016): 107-114. Web. 5 Mar. 2021
Abbas-Temirek, Husien, AND Abo-Bakr, Ahmed. "Reactions with heterocyclic amidines: Synthesis of several new pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a][1,3,5]triazines" European Journal of Chemistry [Online], Volume 7 Number 1 (31 March 2016)

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European Journal of Chemistry 2016, 7(1), 107-114 | doi: https://doi.org/10.5155/eurjchem.7.1.107-114.1369 | Get rights and content

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