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العنوان
Synthesis of Some New Heterocycles With Anticipated Biological Activities /
المؤلف
Mirna Talaat Helmy Saadan,
هيئة الاعداد
باحث / Mirna Talaat Helmy Saadan
مشرف / Hamdi Mahmoud Hassaneen
مشرف / Farid Mohamed Ahmed Sroor
مناقش / Mohamed Abdel-Moety Mohamed
مناقش / Helmut Duddeck
الموضوع
organic chemistry
تاريخ النشر
2022.
عدد الصفحات
149 p. :
اللغة
الإنجليزية
الدرجة
الدكتوراه
التخصص
Chemistry (miscellaneous)
تاريخ الإجازة
19/6/2022
مكان الإجازة
جامعة القاهرة - كلية العلوم - Chemistry
الفهرس
Only 14 pages are availabe for public view

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from 198

Abstract

The present dissertation includes the synthesis of new heterocyclic compounds by treatment of N-(4-nitrophenyl)furan-2-carbohydrazonoyl chloride 2A and N-(4-nitrophenyl)thiophene-2-carbohydrazonoyl chloride 2B with acetylacetone 3 in the presence of ethanolic sodium ethoxide solution afforded pyrazoles 4A,B. Reaction of 4A,B with aryl aldehydes 5a-g in ethanol in the presence of sodium hydroxide solution yielded the pyrazolyl-chalcones 6A and 6B. Chalcones 6Aa and 6Ae were reacted with hydrazonoyl chlorides 2B-F in ethanol in the presence of triethylamine to yield the corresponding pyrazolines 8 which upon refluxed with chloranil in xylene afforded pyrazoles 10. Refluxing of chalcones 6Aa-g with hydrazine hydrate in ethanol yielded the corresponding pyrazolines 11a-g. Refluxing of chalcone 6Ad with hydrazine hydrate in boiling formic acid or acetic acid afforded the corresponding products 12d or 13d, respectively. Stirring of pyrazoline derivative 11d with sodium nitrite in the presence of hydrochloric acid or with phenyl isothiocyanate in dry ether afforded the corresponding products 14d or 15d, respectively. Enaminone 16 was prepared via heating of pyrazole compound 4A with DMF-DMA at reflux. Treatment of enaminone 16 with hydrazonoyl halides 2I-O in chloroform in the presence of triethylamine at reflux gave dipyrazolyl methanone derivatives 17I-O. Treatment of compounds 17I-K and 17L-N with hydrazine hydrate in ethanol at reflux afforded pyrazolopyridazinones 21I-K and pyrazolopyridazines 22L-N, respectively. Stirring of hydroximoyl chlorides 23a,b with enaminone 16 in chloroform in the presence of triethylamine at room temperature afforded isoxazole derivatives 24a,b which upon refluxed with hydrazine hydrate in ethanol gave isoxazolopyridazines 26a,b. Refluxing of enaminone 16 with the appropriate amines 27a-f in ethanol in the presence of acetic acid afforded the substituted products 28a-f. Reaction of hydrazonoyl chloride 2A with 2-((methylthio)carbonthioyl)hydrazones 31 and 35-40 at room temperature in absolute ethanol in the presence of triethylamine afforded 1,3,4-thiadiazole derivatives 34 and 41-46. Compound product 47 was prepared via refluxing of pyrazole compound 4A with methyl hydrazinecarbodithioate 29 in absolute ethanol in the presence of drops of hydrochloric acid. Refluxing of 47 with hydrazonoyl halides 2A-P in absolute ethanol in the presence of triethylamine afforded 1,3,4-thiadiazole derivatives 50A-P. The structures of the all new compounds were elucidated from their elemental analyses and their spectral data (IR, 1H NMR, 13C NMR and MS). Antimicrobial and antitumor activities for some of new synthesized compounds were studied