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العنوان
Synthesis and Reactions of some heterocyclic compounds and studying their behavior towards electrophilic and nucleophilic reagents \
المؤلف
Mahmoud, Mohammed Gamal Mohammed.
هيئة الاعداد
باحث / محمد جمال محمد محمود
مشرف / ماهر عبد العزيز محمود الحشاش
مشرف / سامح احمد محمد احمد رزق
مشرف / عبير محمد السيد النجار
تاريخ النشر
2021.
عدد الصفحات
260 p. :
اللغة
الإنجليزية
الدرجة
الدكتوراه
التخصص
Organic Chemistry
تاريخ الإجازة
1/1/2021
مكان الإجازة
جامعة عين شمس - كلية العلوم - الكيمياء
الفهرس
Only 14 pages are availabe for public view

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Abstract

The original work of this thesis can be classified into three parts:
First part: In the present work, reaction of 3-nitrophthalic anhydride with anthranilic acid to afford the corresponding anthranil that is treated with acetic anhydride yielded the 2-benzoxazinonyl-5-nitrobenzoic acid (BNBA) could be isomerized to the stereogenic 9-nitrobenzoxazinone[2,3-a]isoindolinone acetate (NBIA) via basic reaction conditions. A reaction of the BNBA→NBIA was allowed with series of nitrogen nucleophiles such as formamide and hydrazine derivatives e.g. hydrazine hydrate, hydroxyl amine, acetic hydrazide, thiosemicarbazide, thiocarboihydrazide and some amino acid e.g. glycine, alanine and some aliphatic amine e.g. octyl amine, decyl amine and aromatic amine e.g. aniline, o-toluidine, 4-aminobenzoic acid and carbon nucleophiles such as malononitrile and diethylmalonate. The basicity of previous nucleophiles and thermal stability of the products can be controlled on the course of reaction. The chemical structure of the synthesized compounds can be confirmed by micro-analytical, spectral data and they optimized by quantum chemical parameters (DFT study) to identify the thermal stability of the products .
Second part: In this part, reaction of benzoyl chloride with anthranilic acid to afford the corresponding benzoxazinone that is treated with different nitrogen and sulfur nucleophiles to afford the corresponding quinazolinone and thio quinazolinone derivatives, and also react with some metals to form metalo organic complexes with high biological activity.
Also quinazolinones react with different carbon electrophiles and react with metals to afford the corresponding organometallic complexes.
Third part: The data obtained from the molecular modeling were correlated with those obtained from the biological screening. A novel sequence of quinazoline derivatives were synthesized, evaluated for their algaecides activity against Compounds 1b, 2, 3a and 6 showed the highest algaecides activities of this series with relatively low toxicity in the median lethal dose test. The obtained results proved that the most active compounds could be a useful model for future design, adaptation and investigation to construct more active analogs.