Synthesis Of Fusedheterocyclicquinazolines

Quinazolinones are widely used in pesticide and pharmaceutical fields because of its good physical pharmacological activity. Quinazolinones have anti-tumor, anti-cancer, anti-hypertensive, anti-malarial, anti-HIV activity in medicine and antibacterial, herbicidal, insecticidal activity in pesticides. In addition, quinazolinone compounds have a conjugate structure, so the compound has strong fluorescence properties, it can be used as a fluorescence molecular probe.Firstly, 2-amino-3-cyano-pyran derivatives were prepared by the reaction of 2-arylylidene malononitrile derivatives with ethyl acetoacetate via Michael reaction in this article. The 2-amino-3-cyano-pyran derivatives was mixed with excess triethyl orthoformate, and heated to reflux, then eight intermediate 6-(ethoxymethylene)amino pyran derivatives which have not been reported were obtained. Finally, eight novel pyrano[2',3':4,5]pyrimido [6,1-b]quinazolinone derivatives were synthesized by the reaction of methyl anthranilate with 6-(ethoxymethylene)amino pyran derivatives in acetic acid under refluxing.Then, 2-amino-3-cyano-benzopyano derivatives were prepared by the reaction of 2-arylylidene malononitrile derivatives with 5-substituted-1,3-cyclohexanedione via Michael reaction. 2-Amino-3-cyano-benzopyano derivatives was mixed with excess triethyl orthoformate, and heated to reflux, then intermediate 2-(ethoxymethylene)aminobenzo pyano derivatives were obtained. Finally, twenty-four novel benzopyrano[2',3':4,5]pyrimido [6,1-b]quinazolinone derivatives were synthesized by the reaction of methyl anthranilate with 2-(ethoxymethylene)aminobenzopyano derivatives in acetic acid under refluxing.In this synthesis method, acetic acid as solvent, and the product was precipitated after completion of the reaction. The method has many advantages, such as simple operation, less by-products, convenient post treatment, mild reaction conditions, environmental friendly, et al.In this paper, a total of forty new nitrogen-containing heterocyclic derivatives were synthesized, and characterized by IR, 1H NMR and MS. In order to determine the stereochemical structure of the compound, some compounds have been growing a single crystal by the solution method. The single crystals of 3c, 3e, 4b, 4c, 7c, 7h, 7n and 7s were obtained and determined by single crystal X-ray diffraction analysis.