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Benzoylacetone as a Building Block in Heterocyclic Synthesis: Synthesis of Polyfunctionally Substituted Pyridinethione and Its Derivatives

DOI: 10.4236/oalib.1101274, PP. 1-9

Subject Areas: Organic Chemistry, Analytical Chemistry

Keywords: Pyridines, Pyrimidines, Pyridinthione, Pyridothienopyrimidine and Isoquinolines

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Abstract

The Hantzsch amide derivatives 1 are prepared by reaction of a mixture of two moles of benzoylacetone, aqueous ammonia and aromatic aldehydes. Also, the reaction of benzoylacetone with a mixture of urea or thiourea and aromatic aldehydes afforded pyrimidine derivatives 2a-h. Pyridinethione derivative 3 was reacted with α–haloketones and α–halonitriles 4a-e to afford the S-alky- lated derivatives 5a-e which cyclized into 6b-e and 7. Reactions of compound 7 with glacial acetic acid/acetic anhydride gave 8 which led to 9a and 9b on treatment with ammonium acetate/acetic acid and aniline. Also, treatment of 7 with formamide, hydrazine hydrate and benzoyl isothiocyanate afforded 10, 11 and 13. Reactions of 3 with arylidenemalononitrile 14 in ethanolic triethylamine yielded 1:1 addact 17a-c.

Cite this paper

Hussein, A. H. M. , Abu-Shanab, F. A. and Mousa, S. A. H. S. (2015). Benzoylacetone as a Building Block in Heterocyclic Synthesis: Synthesis of Polyfunctionally Substituted Pyridinethione and Its Derivatives. Open Access Library Journal, 2, e1274. doi: http://dx.doi.org/10.4236/oalib.1101274.

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