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العنوان
Synthesis of new heterocyclic compounds containing triazole rings /
المؤلف
Sheta, Rasha Adel Abo El-Fath.
هيئة الاعداد
باحث / رشا عادل أبو الفتوح
مشرف / إبراهيم فتحى زيد
مشرف / عادل عبد الهادى نصار
مشرف / عبدالله شعبان العتراوى
الموضوع
Triazoles. Chemistry. Heterocyclic chemistry.
تاريخ النشر
2016.
عدد الصفحات
125 p. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
الكيمياء
الناشر
تاريخ الإجازة
9/6/2016
مكان الإجازة
جامعة المنوفية - كلية العلوم - الكيمياء
الفهرس
Only 14 pages are availabe for public view

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Abstract

Reaction of p-methoxybenzaldhyde with malononitrile in the presence of a catalytic amount of piperidine under reflux afforded 2-(4-methoxybenzylidene)malononitrile (2) in 86 % yield (Scheme 1). A solution of 2 and thioglycolic acid in ethanol and a catalytic amount of piperidine was refluxed for to afford the dicarbonitrile 3 in 86 % yield (Scheme 2). Stirring of a mixture of cyanohydrazide and 2 in absolute ethanol containing a catalytic amount of piperidine gave 4 in 90 % yield (Scheme 3).
A mixture of equimolar amounts of 4 and benzaldehyde (5) in ethanol was allowed to reflux to 6 in 75 % yield (Scheme 4). A mixture of equimolar amounts of 4 and salicylaldehyde (7) in ethanol was allowed to reflux to give 8 in 77 % yield (Scheme 5). A mixture of equimolar amounts of 4 and p-chlorobenzaldehyde (9) in ethanol was allowed to reflux to afford 10 in 81 % yield (Scheme 6).
English Summary
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A mixture of equimolar amounts of 4 and p-florobenzaldehyde (11) in ethanol was allowed to reflux to afford 12 in 78 % yield (Scheme 7). A mixture of equimolar amounts of 4 and p-anisaldehyde (13) in ethanol was allowed to reflux to give 14 in 84 % yield (Scheme 8). A mixture of equimolar amounts of 4 and p-nitrobenzaldehyde (15) in ethanol was allowed to reflux. The resulting precipitate was filtered off, washed several times with ethanol, and recrystallized from glacial acetic acid to afford 16 in 80 % yield (Scheme 9).
A mixture of equimolar amounts of 4 and furfural (17) in ethanol was allowed to reflux to give 18 in 77 % yield (Scheme 10). A solution of 4 in freshly distilled acetic anhydride and acetic acid (1:1) was reflux for 10 h. The precipitate formed on cooling to room temperature was filtered off and recrystallized from DMF to afford 19 in 85 % yield (Scheme 11). A mixture of equimolar amounts of 4 and ethylacetoacetate was refluxed for 3 h in ethanol. The precipitate formed was filtered off,
washed several times with ethanol, and recrystallized from aqueous DMF to afford 20 in 86 % yield (Scheme 12). A mixture of equimolar amounts of 4 and D-xylose in ethanol was allowed to reflux for 7 h. The resulting precipitate was filtered off, washed several times with ethanol, and recrystallized from glacial acetic acid to afford 21 in 81 % yield (Scheme 13). A mixture of equimolar amounts of 4 and D-galactose in ethanol was allowed to reflux for 9 h. The resulting precipitate was filtered off, washed several times with ethanol, and recrystallized from glacial acetic acid to afford 22 in 78 % yield (Scheme 14).
A mixture of ethyl cyanoacetate, thiourea and p-anisaldehyde in sodium ethoxide was stirred for 24 h at room temperature and poured onto ice-water, and acidified with dil. HCl to give 23 in 76 % yield (Scheme 15). Equimolar mixture of 23 and ethanolamine was heated to reflux for 10 h. The reaction mixture was concentrated under reduced pressure; the separated solid was collected by filtration and recrystallized from glacial acetic acid to give 24 in 47 % yield (Scheme 16). A mixture of 23 and phenacylbromide was refluxed in ethanol for 5 h. After completion of the reaction, the precipitate formed on hot was
filtered, washed with ethanol, and dried to afford 26 in 70 % yield (Scheme 17). A mixture of compound 23, chloroacetic acid, benzaldehyde in a mixing solvent of acetic anhydride and acetic acid in the presence of fused sodium acetate was refluxed for 2 h. The solid obtained was recrystallized from proper solvent to afford 27 in 68 % yield (Scheme 18). A mixture of compound 23, chloroacetic acid, p-chlorobenzaldehyde in a mixing solvent of acetic anhydride and acetic acid in the presence of fused sodium acetate was refluxed for 3 h. The solid obtained was recrystallized to afford 28 in 68 % yield (Scheme 19). A mixture of compound 23, chloroacetic acid, p-nitrobenzaldehyde in a mixing solvent of acetic anhydride and acetic acid in the presence of
fused sodium acetate was refluxed for 4 h. The solid obtained was recrystallized to afford 29 in 69 % yield (Scheme 20). A mixture of the thiouracil derivative 23 and anthranilic acid was refluxed in sodium ethoxide solution for 12 h, cooled, and poured onto acidified ice-water. The obtained solid was filtered off, washed with water, dried, and recrystallized to afford 31 in 86 % yield (Scheme 21).