7- or 9-substituted-2-amino-4-hydroxy-7-methoxy-5H-chromeno-[4,3-d]-pyrimidine-5-one, 3a,b, were prepared via cyclocondensation of 6- or 8-substituted-3-ethoxycarbonyl coumarin, 2, with guanidine hydrochloride in presence of anhydrous potassium carbonate. Acetylation and alkylation of compounds with acetic anhydride and ω-bromomethyl aryl ketones yielded the corresponding N-acetyl derivatives, 4a,b, and 8- or 10-substituted-5-hydroxy-1-p-tolyl-6-H-chromeno[3,4-e] imidazo[1,2-a] pyrimidine-6-one, 5a,b,. Treatment of compound 3a with ethylchloroacetate and methyl acrylate afforded the corresponding benzopyrano-[4,3-d]-imidazolidino-[2,1-b]-pyrimidine, 6, and benzopyrano-[4,3-d]-pyrimidino-[2,1-b]-pyrimidine, 7, respectively. Some of the new compounds were evaluated for cytotoxicity activity against a hepatocellular carcinoma cell line.
Research on Chemical Intermediates – Springer Journals
Published: Apr 23, 2013
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