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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
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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DOI Link: https://doi.org/10.5155/eurjchem.3.2.241-246.597
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