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العنوان
Synthesis and reactions of some new isatin mannich bases and related compounds of expected biological activity /
المؤلف
El-Mettwaly, Mohamed El-Mettwaly Hammouda.
هيئة الاعداد
باحث / Mohamed El-Mettwaly Hammouda El-Mettwaly
مشرف / E.M.Afsah
مشرف / A.A.Fadda
باحث / Mohamed El-Mettwaly Hammouda El-Mettwaly
الموضوع
Biological activity.
تاريخ النشر
2012.
عدد الصفحات
254 p. :
اللغة
الإنجليزية
الدرجة
الدكتوراه
التخصص
الكيمياء
تاريخ الإجازة
1/1/2012
مكان الإجازة
جامعة المنصورة - كلية العلوم - Department of Chemistry.
الفهرس
Only 14 pages are availabe for public view

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from 254

Abstract

The material presented in this work is separated into three main parts: 1: Synthesis of Some New Mannich Bases and Bis(Mannich Bases) Related to Isatin Schiff Bases.1,1: isatin 1 was treated with 2-aminothiazole, 5-aminotetrazole and 2-amino-3-hydroxypyridine to give the corresponding 2 - 4. Treatment of them with piperidine and formaldehyde afforded 5, 6 and 7. Treating 3 with formaldehyde and N-methyl-D-glucamine to afford the polyhydroxy Mannich base 8. The analogous reaction of 4 with diethanolamine gave 9. 1,2: The use of 5-aminotetrazole as the amine component in the Mannich reaction with 3 lead to the formation of 10. Treating compounds 2 - 4 with benzaldehyde and 2-aminothiazole, p-anisidine, 5-aminotetrazole and 2-amino-3-hydroxypyridine to afford 11-14. Treating 3 and 4 with p-hydroxybenzaldehyde and p-anisidine yielding compounds 15 and 16. 2,1: The reaction of isatin 1 or its Mannich base 36 with the hydrazide 35 afforded 37 and 38 (Scheme 8). The periodate oxidation of the tetrahydrocarbazole moiety of 37 and 38 gave compounds 39 and 40. 41 was treated with 42 to afford 43 in a good yield (Scheme 9).The formation of 44, has been achieved by the periodate oxidation of the tetrahydrocarbazole moiety of compound 43. Compound 1 was treated with 45 and formaldehyde to give a mixture, which was separated by column chromatography into the new Mannich bases 46 and 47. The periodate oxidation of the tetrahydrocarbazole moiety of 46 is of particular interest, because it provides access to hexahydrobenzo[b]azonines of the type 48 having an indolin-2,3-dione as a structural unit.Thus, compound 46 was subjected to the periodate oxidation to afford 48. Compound 48 has been used as a precursor to 49, the reaction of 46 with p-aminophenol gave the Schiff base 50, which was subjected to periodate oxidation to give 51. 2,2: In the course of this study, isatin 1 was treated with 52, 53 and 54 to give 55, 56 and 57 respectively (Scheme 12). 3: Addition reaction to arylidine of isatin using thiophenol and oxidation reaction. The compound 74 was subjected to dehydration to give compound 75, which was treated with piperidine to afford compound 76. The synthesis of compound 77 has been achieved on treating 75 with piperazine. The reaction of compound 75 with thiophenol gave compound 78, which was oxidized to give 79. The base catalyzed addition of dimethyl phosphite to compound 75 and 80, afforded the compounds 81 and 82 respectively. The synthesis of compound 85 has been achieved by treating 83 with 84 in presence of diethyl amine.