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

This thesis comprises four chapters. The first chapter is an introduction which consists of a brief literature survey on the recent trends in the synthesis of thieno[2,3- d]pyrimidines, urea, thiourea, thiazole, oxazole derivatives and thieno triazolopyrimidines, in addition to an account on their cytotoxic activity. The second chapter presents the objectives of the work, in addition to the Schemes designed for the preparation of the target compounds. Scheme for starting materials describes the preparation of 2-amino-4,5,6,7- tetrahydro[1]benzothiophene-3-carbonitrile (Ia) followed by reaction with formic acid to yield 5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (II) which reacted with phosphorous oxychloride to afford the key intermediate III. Compound III was then reacted with p-phenylene diamine or hydrazine hydrate to obtain the amino derivative IV and the hydrazinyl derivative V, respectively. It also includes the preparation of 2-amino-4,5,6,7-tetrahydro[1]benzothiophene-3- carboxamide (Ib) which was reacted with chloroacetyl chloride to produce VI. Scheme 1 involves the reaction of IV with the appropriate isothiocyanate or isocyanate to yield two series of thienopyrimidine thiourea and urea derivatives VIIa-g & IXa-e. Compounds VIIa, VIIe, IXb & IXd were further reacted with 4- bromophenacyl bromide to afford the title products VIIIa,b & Xa,b. Scheme 2 comprises the synthesis of 2-(((4-aminophenyl)amino)methyl)- 5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one (XI) via the reaction of VI with p-phenylene diamine, followed by the reaction of XI with the appropriate isothiocyanate to yield a series of thienopyrimidine thiourea derivatives XIIa-e. Scheme 3 is concerned with the preparation of the compounds XIIIa-e through the reaction of the hydrazinyl derivative V with the respective isocyanate

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