European Journal of Chemistry

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

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Published: Jun 30, 2012
DOI: https://doi.org/10.5155/eurjchem.3.2.241-246.597
Keywords:
S-glycosyl, Thienopyrimidine, S-alkyl pyrimidine, Pyrimidopyrimidine, Mercaptopyrimidine, Tetrazolopyrimindine derivatives
Section
Research Article
Issue
Vol. 3 No. 2 (2012): June 2012
Dates
Received 2012-02-10
Accepted 2012-03-22
Published 2012-06-30


Main Article Content

Wesam Saber Shehab
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt
Enaiat Kamel Mohamed
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt

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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Shehab, W. S.; Mohamed, E. K. Synthesis of Some New S-Glycosyl Pyrimidine and Condensed Pyrimidine Derivatives. Eur. J. Chem. 2012, 3, 241-246.

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