European Journal of Chemistry 2012, 3(2), 241-246 | doi: https://doi.org/10.5155/eurjchem.3.2.241-246.597 | Get rights and content

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Synthesis of some new S-glycosyl pyrimidine and condensed pyrimidine derivatives


Wesam Saber Shehab (1,*) , Enaiat Kamel Mohamed (2)

(1) Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt
(2) Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt
(*) Corresponding Author

Received: 10 Feb 2012 | Revised: 05 Mar 2012 | Accepted: 22 Mar 2012 | Published: 30 Jun 2012 | Issue Date: June 2012

Abstract


Mercaptopyrimidine (4) was synthesized by the reaction of isothiocyanate and acrylate (1). It was allowed to react with preacetylated sugar bromide and/or halomethylene derivatives to produce alkylated pyrimidines (5,7a-d). Hydrolysis of compound (5) produced compound (6). Interacyclization of compounds (7a-d) afforded thienopyrimidines (8a-d). Moreover oxidation of compound (7b) gave the corresponding thienopyrimidine dioxide (9). Cyanoethylation of compound (4) afforded compound (10) that reacted with hydrazine hydrate to give pyrazolopyrimidine (11). Oxidation of compound 4 afforded bisulphide (12). The cycloaddition product (13) was obtained by reaction of compound 4 with maleic anhydride. Pyrimidopyrimidine, pyrimidopyridazine and tetrazolopyriminde derivatives (16-20) were obtained by reaction of 4-chloropyrimidine (15) with thiourea, benzilhydrazone and sodium azide, respectively. N-alkylated pyrazolopyrimidine (21) was obtained by reaction of compound (15) with acetophenonehydrazone.

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Keywords


S-glycosyl; Thienopyrimidine; S-alkyl pyrimidine; Pyrimidopyrimidine; Mercaptopyrimidine; Tetrazolopyrimindine derivatives

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DOI: 10.5155/eurjchem.3.2.241-246.597

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Funding information


Zagazig University, Zagazig, Egypt

Citations

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[1]. Wesam S. Shehab, Ahmed F. EL-Farargy, Abdou O. Abdelhamid, Maged A. Aziz
Synthesis and biological application of pyranopyrimidine derivatives catalyzed by efficient nanoparticles and their nucleoside analogues
Synthetic Communications  49(24), 3560, 2019
DOI: 10.1080/00397911.2019.1679538
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[2]. Mohamed H. M. AbdEl‐Azim, Maged A. Aziz, Samar M. Mouneir, Ahmed F. EL‐Farargy, Wesam S. Shehab
Ecofriendly synthesis of pyrano[2,3‐ d ]pyrimidine derivatives and related heterocycles with anti‐inflammatory activities
Archiv der Pharmazie  353(9), 2000084, 2020
DOI: 10.1002/ardp.202000084
/


[3]. Wesam S. Shehab, Walaa H. El-Shwiniy
Nanoparticles of manganese oxides as efficient catalyst for the synthesis of pyrano[2,3-d]pyrimidine derivatives and their complexes as potent protease inhibitors
Journal of the Iranian Chemical Society  15(2), 431, 2018
DOI: 10.1007/s13738-017-1244-4
/


[4]. A. Pekparlak, Ö. Tamer, S.D. Kanmazalp, N. Berber, M. Arslan, D. Avcı, N. Dege, E. Tarcan, Y. Atalay
Synthesis, crystal structure, spectroscopic (FT-IR, 1H and 13C NMR) and nonlinear optical properties of a novel potential HIV-1 protease inhibitor
Chemical Physics Letters  742, 137171, 2020
DOI: 10.1016/j.cplett.2020.137171
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[5]. Rambhau P. Gore, Ambarsing P. Rajput
A review on recent progress in multicomponent reactions of pyrimidine synthesis
Drug Invention Today  5(2), 148, 2013
DOI: 10.1016/j.dit.2013.05.010
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How to cite


Shehab, W.; Mohamed, E. Eur. J. Chem. 2012, 3(2), 241-246. doi:10.5155/eurjchem.3.2.241-246.597
Shehab, W.; Mohamed, E. Synthesis of some new S-glycosyl pyrimidine and condensed pyrimidine derivatives. Eur. J. Chem. 2012, 3(2), 241-246. doi:10.5155/eurjchem.3.2.241-246.597
Shehab, W., & Mohamed, E. (2012). Synthesis of some new S-glycosyl pyrimidine and condensed pyrimidine derivatives. European Journal of Chemistry, 3(2), 241-246. doi:10.5155/eurjchem.3.2.241-246.597
Shehab, Wesam, & Enaiat Kamel Mohamed. "Synthesis of some new S-glycosyl pyrimidine and condensed pyrimidine derivatives." European Journal of Chemistry [Online], 3.2 (2012): 241-246. Web. 26 Oct. 2021
Shehab, Wesam, AND Mohamed, Enaiat. "Synthesis of some new S-glycosyl pyrimidine and condensed pyrimidine derivatives" European Journal of Chemistry [Online], Volume 3 Number 2 (30 June 2012)

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