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Abstract
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The Isobenzofuranone and indolinones are of the important classes of O- and N-heterocyclic compounds. Also spiro-heterocyclic systems are very useful moieties that display a wide range of biological, pharmacological, and medicinal properties. Furthermore eight-membered and larger N-containing fused ring systems have shown substantial bioactivity. Azocine fragment was found in many indole alkaloids as anti-tumor, anti- insect and inhibitor of acetylcholinesterase.
In this thesis, highly efficient methods and safe for the synthesis of nitrogen and oxygen containing heterocycles based on the oxidation of diols formed from the reaction of ninhydrin with aromatic amines and diols formed from the reaction of acenaphthenequinone with aminouracil have been presented.
At first 6b,11b-dihydroxy-10,11b-dihydro-6bH-acenaphthopyrrolo[2,3-d] pyrimidine-9,11-diones were synthesized from the reaction of acenaphthenequinoe and aminouracil derivatives using 10% AcOH in ethanol as solvent at 60-70oC. Then, 7H-naphtho[1,8-ef]pyrimido[4,5-b]azocine tetraone drivatives were synthesized by the oxidative cleavage of 6b,11b-dihydroxy-10,11b-dihydro-6bH-acenaphthopyrrolo[2,3-d] pyrimidine-9,11-diones using periodic acid or lead tetraacetate in acetic acid at room temperature in water in good yield (Scheme 1).
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