Synthesis of Certain Fused Thienopyrimidines of Biological Interest /
تشييد بعض مشتقات الثينوبيريميدينات الملتحمة ذات الاهمية البيولوجية
Asmaa Elsayed Abdellatief Kassab ; Supervised Bothaina Abdelfattah Mousa , Manal Mostafa Kandeel , Omneya Mahmoud Khalil
- Cairo : Asmaa Elsayed Abdellatief Kassab , 2006
- 141P : ill ; 30cm
Thesis (M.Sc.) - Cairo University - Faculty Of Pharmacy - Department Of Organic Chemistry
The thesis is prefaced by an account on the synthesis of cycloalkeno - thieno[2 , 3 - d]pyrimidin - 4 (3H) - ones and triazolocycloalkenothienopyrimidine derivativesIn addition , a survey covering the different biological activities of some cycloalkenothienopyrimidines and their fused systems is givenPreparation of the root compounds vizethyl 2 - aminocycloocteno - [b]thiophene - 3 - carboxylate (II) , ethyl 2 - (3 - substituted thioureido) cycloocte - no[b]thiophene - 3 - carboxylates (IIIa and b) , 3 - substituted - 2 - thioxo - 1H , 3H - cyc - loocteno[4 , 5]thieno[2 , 3 - d]pyrimidin - 4 - ones (IVa and b) and 3 - amino - 2 - substit - uted aminocycloocteno[4 , 5]thieno[2 , 3 - d]pyrimidin - 4 (3H) - ones (XIIa and b) is presentedScheme 1 is concerned with the interaction of the ortho amino ester II with isothiocyanates to furnish IIIa and bFurthermore , cyclization of the latter was accomplished smoothly in ethanol saturated with dry hydrogen chloride to give the 2 - mercaptothienopyrimidin - 4 (3H) - ones IVa and b which was alkylated using different alkyl halides (methyl iodide , ethyl iodide and allyl bromide) to afford Va - fs regards Scheme 2 , it involves the reaction of IVa and b with ethyl chloroacetate to give 2 - ethoxycarbonylmethylthio - 3 - substituted cyclooct - eno[4 , 5]thieno[2 , 3 - d]pyrimidin - 4 (3H) - ones (VIa and b) Reaction of the latter with hydrazine hydrate gave the corresponding hydrazide VIIa and bCondensation of VIIa and b with different aromatic ketones (acetophenone , 4 - chloroacetophenone , 4 - aminoacetophenone and 4 - hydroxyacetophenone) afforded the corresponding arylethylidene derivatives VIIIa - hThe reaction of VIIIa - h with acetic anhydride yielded 2 - (acetyloxyethynylthio) - 3 - substituted cycloocteno[4 , 5]thieno[2 , 3 - d]pyrimidin - 4 (3H) - ones (XIa and b) , instead of expected 1 , 3 , 4 - oxadiazoline derivativesIn addition , 3 - phenyl -