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Molecules 2012, 17(10), 11538-11553; doi:10.3390/molecules171011538

3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d ]pyrimidine: An Effecient Key Precursor for Novel Synthesis of Some Interesting Triazines and Triazepines as Potential Anti-Tumor Agents

1
Chemistry Department, Faculty of Science, Fayoum University, El-Fayoum, 63514, Egypt
2
Department of Chemistry, Faculty of Science, University of Cairo, Giza, 12613, Egypt
*
Author to whom correspondence should be addressed.
Received: 6 August 2012 / Revised: 27 August 2012 / Accepted: 20 September 2012 / Published: 27 September 2012
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Abstract

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-3H-chromeno-[2,3-d]pyrimidine (1) and reagents such as hydrazonyl halides 2 to furnish triazine derivatives 4al. 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 10ad 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 18ac. 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.
Keywords: pyrimidotriazines; pyrimidotriazepinones; triazolopyrimidines; antitumor activity; hydrazonoyl halides pyrimidotriazines; pyrimidotriazepinones; triazolopyrimidines; antitumor activity; hydrazonoyl halides
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Badrey, M.G.; Gomha, S.M. 3-Amino-8-hydroxy-4-imino-6-methyl-5-phenyl-4,5-dihydro-3H-chromeno [2,3-d ]pyrimidine: An Effecient Key Precursor for Novel Synthesis of Some Interesting Triazines and Triazepines as Potential Anti-Tumor Agents. Molecules 2012, 17, 11538-11553.

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