Synthesis of new heterocycles via C-C bond formation reactions / Hadeel Fawzi Hammad Mohammed Radwan ; Supervised Mahfouz Ali Abdelaziz , Ahmed Fathy Darweesh , Amr Mohamed Abdelmoniem

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

Simple and efficient procedures have been developed for the synthesis of novel series of bis(9,10-diaryl-hexahydroacridine-1,8-diones) in which the two acridine moieties were linked to aliphatic, aromatic or heteroaromatic spacers via ether or ester linkages.The target products were performed in good to excellent yields via a multi-component reaction of the appropriate aromatic amine, 5,5-dimethyl-1,3-cyclohexanedione, and the corresponding bisaldehydes in acetic acid at reflux. The reactions were also proceeded to give the target products in good yields via a multi-component reaction of the appropriate 3- (arylamino)cyclohex-2-en-1-one, 5,5-dimethyl-1,3-cyclohexanedione, and the corresponding bis-aldehydes under similar conditions.Bis-alkylation of the appropriate hexahydroacridine- 1,8-dione with the corresponding dihalo compound in basic medium was also proved to be an effective strategy for the synthesis of the target products. The multi-component reaction of the appropriate aromatic amine, bis-aldehydes and barbituric acid or 1,3-dimethylbarbituric acid, instead of 5,5-dimethyl-1,3-cyclohexanedione, afforded the corresponding Knoevenagel condensation adducts in good yield and unfortunately, the expected bis(pyrimido[4,5- b]quinoline-2,4,6(1H,3H,5H)-trione)) could not be isolated even in traces

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