Thesis (M.Sc.) - Cairo University - Faculty of Science - Department of Organic Chemistry

The original work of this thesis is composed of three parts. In the first part, a series of N-((1,2,4-triazol-3-yl)-enamine and N-((1,2,3-triazol-4-yl)-enamine were prepared and reacted with Ü,Ý-unsaturated nitriles to yield novel N-(4H-1,2,4-triazol-3-yl)- hexahydroquinoline-3-carbonitrile and their fused and spiro derivatives. Dimroth type rearrangement of the prepared quinoline derivatives was observed in acetic anhydride leading to the formation of substituted pyrimido[4,5-b]quinoline, spiro[indoline-3,5'-pyrimido[4,5- b]quinoline] and spiro[indoline-3,5'-[1,3]oxazino[4,5-b]quinoline] compounds. The second part, A simple and efficient one-pot synthesis of novel thieno[3',2':5,6]pyrimido[1,2- a]quinoline-2-carboxylates and their spirooxindole derivatives were accomplished via the Michael addition reaction of a cyclic Ý-enaminone incorporating thiophene moiety with Ü,Ý- unsaturated nitrile derivatives in EtOH at reflux in the presence of piperidine. Also, novel spirocyclic 2-oxoindole derivatives of thieno[3',2':5,6]pyrimido[1,2-a]quinolone were synthesized by the reaction this cyclic Ý-enaminone with 3-cyanomethylidene 2-oxoindole derivatives in refluxing EtOH. In the third part, The three-component reaction of dimedone, malononitrile dimer and bis-aldehydes in ethanol at reflux in the presence of piperidine afforded bis(5H-chromeno[2,3-b]pyridine-3-carbonitrile) derivatives in excellent yields. The chemical structures of all new synthesized products were confirmed based on the different spectral tools and elemental analysis data

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