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Abstract
Abstract
Heterocyclization of 4-mercapto-5-acetyl-pyrimidine derivative
Pyrimidine derivatives and heteroannelated pyrimidines continue to attract great interest due to the wide variety of interesting biological activities observed for this compounds, such as anti-convulsant1, anti-inflamatory2, bactericidal3, fungicidal4, and anti-fertility5 activities .
The enaminic carbon of enaminone(1) was added to the electrophilic carbon of 3-chloro- benzoyl isothiocyanate(2) to produce 4-mercapto-5-acetylpyrimidine derivative (3).Comp- ound (3)seemed to be of suitable located funactionality for further funclization and hetero- cyclization. Thus compound (3)was reacted with activated halomethylone in basicmedium to give thienopyrimidine presumably via the alkylthio derivative (4).Compound(5)undergo further cyclization to give benzoxazinylthieno [2,3]pyrimidines derivative(6). Reaction of compound(6) with formamide resulted in ring transformation affording qunoxazinyl thienopyrimidine(7). When compound (3) was allowed to react with NaOCl in the prescence of NH4OH resulted in sulphenation followed by intramolecular cyclization affording thiazolopyrimidine (9). Compound (3) undergo michael addition followed by cyclization and subsequent hydrolysis to produce thienopyrimidine (11) when subjected to react with acrylonitrile. Oxidation of compound (3)using iodine gives disulphide (12) )