تحضير وتشخيص بعض المركبات الحلقية غير المتجانسة المشتقة من أورثو-كاربوكسي بنزالديهايد وتقدير فعاليتها البايولوجية

الباحث

ميساء خير الدين شاكر محمود آل ملا خضير

المشرف

مؤيد سالم نوري الجوادي

الجامعة

جامعة الموصل

الكلية / القسم

كلية العلوم / قسم الكيمياء

الشهادة

دكتوراه

السنة

2022

لغة الرسالة

عربي

الكلمات المفتاحية

المركبات الحلقية غير المتجانسة ; أورثو-كاربوكسي بنزالديهايد ; الفعالية البايولوجية ; الكيمياء العضوية

This study included the preparation of a number of various heterocyclic compounds using ortho-carboxybenzaldehyde as a raw material for organic reactions, and then evaluation of the biological activity of a number of them. The preparation process included the following tracks: The first path: This path includes the preparation of Schiff bases (M1-6) from the reaction of ortho-carboxybenzaldehyde with several primary aromatic amines using methyl alcohol as a solvent for the reaction and by adding two drops of acetic acid and then reacted with alpha-chloro acetate chloride to give the four membered ring compounds represented by aztidine-2-on (M7-12) And its reaction with thioglycolic acid in the presence of anhydrous zinc chloride in ethyl alcohol to give five-ring compounds represented by thiazolidine-4-un (M13-18). Whereas, the Schiff bases compounds were reacted with anhydrous malic acid and anhydrous phthalic acid in a medium of ethyl alcohol to give the seven-cyclic compounds represented by 1,3-oxazepine (M19-24) and 1,3-benzooxazepine (M25-30), respectively. The second path: This path includes the preparation of benzimidazoles (M31-36) through the reaction of Schiff bases (M1-6) with ortho-phenylenediamine in ethyl alcohol in the presence of ammonium chloride as a catalyst and at a ratio of (1:1) and also the introduction of Schiff bases (M3) and (M6) which containing two carboxyl groups in the reaction with ortho-phenylenediamine in a ratio of (2:1) to obtain the two compounds (M37 and M38), respectively. The third path: the introduction of compounds (M31-35) in the alkylation reaction in the benzimidazole ring through its reaction with benzyl chloride to give compounds (M39-43) and with alpha-chlorochloride acetate to give compounds (M44-48), as well as with alpha-chloro acid Acetic and ethyl chloroacetate to give compounds )M49-53( and )M54-58(, respectively. The fourth route: esterification of the ortho-carboxybenzaldehyde compound to give the compound 2-formyl ethyl benzoate (M59) and then reacted with simecarbazide in ethyl alcohol to obtain the semicarbazide derivative (M60), which was cyclization using a sodium hydroxide solution (8% NaOH) to give triazole (M61). The fifth path: the reaction of the ester compound (M59) with thiosimicarbazide in ethyl alcohol to obtain the compound (M62), which is cyclization using a solution of sodium hydroxide (8% NaOH) to give triazole (M63), which is subsequently reacted with the primary amines in methyl alcohol in an acidic medium using acetic acid to prepare Schiff base compounds (M64-68). Then it reacted with alpha-chlorochloride acetate to give the four membered ring compounds represented by azitidine-2-on along with the triazole ring in the same compound (M69-73). The sixth path: This path includes the reaction of the ester compound (M59) with hydrazine hydrate in ethyl alcohol to obtain the hydrazide compound (M74), which is reacted with carbon disulfide by stirring in ethyl alcohol and in the presence of potassium hydroxide to give the xanthate salt (M75) which converts to 4-aminotriazole compound (M76) when heated with hydrazine in aqueous media and then reacted with substitutes of benzoic acid in the presence of phosphorous oxytrichloride (POCl3) to form triazole compounds bonded with the thiadiazole ring (M77-80). The seventh path: This path includes the reflux of the hydrazide compound (M74) for (24) hours in a solvent dimethyl sulfoxide (DMSO) to obtain the triazole analogue (M81) that was introduced into the reaction of preparing Schiff bases by reacting with substituted benzaldehyde in a medium of ethyl alcohol and in the presence of a mixture of glacial acetic acid and anhydrous sodium acetate to obtain the compounds (M82-85). All the products were confirmed using available physical methods as well as spectral data using infrared and nuclear magnetic resonance spectrum to prove the structural structure of the resulting compounds. And then studying the effect of some prepared compounds (M7, M9, M13, M16, M19, M24, M25 M30, M65, M67, M34, M38, M44, M50, M72, M76, M79, M80, M81, M82) on four types of Positive and negative bacteria, including gram-positive Staphylococcus aurous and three types of gram-negative bacteria are (Klepsiella pnenmoniao), (E. coli) and finally (Pseudomonas aeroginosa).

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