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العنوان
Synthesis of some quinazoline derivatives of expected biological activity /
المؤلف
Abd El-Wahab, Mohamed Mohamady Ahmed.
هيئة الاعداد
باحث / هحود هحودى أحود عبدالوهاب
مشرف / سامي عبدالغنى عيسوى
مشرف / محمد حلمي عريف
مشرف / علي عبدالمعبود علي
الموضوع
Chemical compounds Chemical reactions. Biochemistry. Chemistry. Chemistry.
تاريخ النشر
2011.
عدد الصفحات
91 p. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
Organic Chemistry
تاريخ الإجازة
1/1/2011
مكان الإجازة
جامعة بنها - كلية العلوم - Chemistry
الفهرس
Only 14 pages are availabe for public view

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Abstract

Polyfunctionally substituted heterocycles are biologically interesting molecules and their chemistry has in the past received interest, so that our work aims to synthesize some bulky substituents benzoxazinone derivatives which has strong conjunction power at position 2. the benzoxazinone derivatives 1 was produced via the reaction of anthranilic acid with dibenzothiophenyl –oxide-4-oxo-butaroyl chloride. During this phase of our research we studied the reaction of 1 with nitrogen nucleophiles namely, hydrazine hydrate, hydroxylamine hydrochloride, benzoyl hydrazine, piperidine, o-phenylenediamine, sodium azide and formamide to give products by ring opening which cyclizes in accordance with the reaction conditions and the nature of the reacting nucleophile. when amino quazolinone 2 reacted with chloroacetyl chloride and acetic anhydride afforded 2-chloro-N-(2-chloroacety)-N-quinazolinyl-acetamide 3 and N-acetyl-N-quinazolinyl-acetamide 4 respecrively. 3-hydroxy quinazolinone 5 can be reacted with ethylchloro acetate and acetylchloride to yield quinazolinyloxy-acetic acid ethylester 6 and quinazolinylester 7. the study extended to include the reaction of benzoxazine 1 with carbon nucleophiles e.g. ethylecetoacetate in pyridine afforded phenyl propionic acid ethyl ester derivative 13 when quinazolinone derivative 16 reacted with carbon electrophiles e.g. chloro acetophenon, benzylchloride and ethylchloroacetate in presence of anhydrous K2CO3 as catalyst and in dry acetone yielded the quinazoline derivatives 17, 19 and quinazolinone derivative 18 quinazolinone derivative 16 was allowed to react with a mixture of PCl5/POCl3 on boiling water bath to yield chloro quinazoline derivative 21. chloroquinazoline 21 reacted with nucleophiles such as:1-sulphur nucleophiles e.g; thioglycolic acid, thiouea and thiophenol to give compounds 22, 23 and 24. 2-nitrogen nucleophiles e.g. sodiumazide, piperidine and o-amino phenol to afford quinazoline derivatives 25, 26 and 27 respectively. when chloroquinazolin 21 reacted with hydrazine hydrate in boiling butanol afforded hydrazino quinazoline derivative 28. Compound 28 can be reacted with carbon disulphide to give compound 29 compound 28 reacted with benzaldehyde in boiling butanol to yield hydrazone derivative 30. chloroquinazoline 21 reacted with carbon nucleophiles such as acetyl acetone in presence of sodium ethoxide and in butanol to yield quinazolinyl peopanone 31.treatment of chloroquinazoline 21 with sulphanilamide in DMF afforded quinazolinylbenzene sulfonamide 32.the biological activity of all synthesized compounds have been studied and some of them have an impressive activity.