A number of interesting heterocycles were prepared through interaction of the intermediate 3-amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3
H-chromeno-[2,3-d]pyrimidine (
1) and reagents such as hydrazonyl halides
2 to furnish triazine derivatives
4a–
l. Reaction of
1 with phenacyl bromide afforded compound
5.
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A number of interesting heterocycles were prepared through interaction of the intermediate 3-amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3
H-chromeno-[2,3-d]pyrimidine (
1) and reagents such as hydrazonyl halides
2 to furnish triazine derivatives
4a–
l. Reaction of
1 with phenacyl bromide afforded compound
5. Moreover, the title compound
1 was subjected to condensation with active methylene compounds (ethyl acetoacetate and ethyl benzoylacetate) to give triazipinones
8a,b. The condensation with aromatic aldehydes afforded either the triazole derivatives
10a–
d or Schiff base
11. In addition, the behaviour of compound
1 towards activated unsaturated compounds namely dimethyl acetylene dicarboxylate and ethoxymethylenemalonitrile was studied and it was found to furnish the triazine
13 and triazepine derivative
15, respectively. Combination of title compound
1 with chlorinated active methylene compounds delivered the triazine derivatives
18a–
c. Reaction of
1 with chloroacetonitrile furnished compound
20. The structures of the products were elucidated based on their microanalyses and spectroscopic data. Finally, the antitumor activity of the new compounds
4a and
8a against human breast cell MCF-7 line and liver carcinoma cell line HepG2 were recorded.
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