TITLE:
Benzoylacetone as a Building Block in Heterocyclic Synthesis: Synthesis of Polyfunctionally Substituted Pyridinethione and Its Derivatives
AUTHORS:
Abdel Haleem Mostafa Hussein, Fathi Ali Abu-Shanab, Sayed Abdel Hamed Sayed Mousa
KEYWORDS:
Pyridines, Pyrimidines, Pyridinthione, Pyridothienopyrimidine and Isoquinolines
JOURNAL NAME:
Open Access Library Journal,
Vol.2 No.1,
January
26,
2015
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.