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العنوان
the use of β-ketoanilides in the synthesis of new heterocyclic compounds /
المؤلف
Rizk, Nanees Nagy Soliman.
هيئة الاعداد
باحث / Nanees Nagy Soliman Rizk
مشرف / Mohamed Abbas El-Metwally
مشرف / Ahmed Fekri Abdel Hak
باحث / Nanees Nagy Soliman Rizk
الموضوع
β-ketoanilides.
تاريخ النشر
2013.
عدد الصفحات
148 p. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
Organic Chemistry
تاريخ الإجازة
1/1/2013
مكان الإجازة
جامعة المنصورة - كلية العلوم - Department of Chemistry
الفهرس
Only 14 pages are availabe for public view

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from 148

Abstract

Acetoacetanilide (1) has been prepared by the reaction of ethyl aceto-acetate and aniline in boiling dry xylene.
Knoevenagel condensation of different aromatic aldehydes e.g. 4-isopropyl-benzaldehyde, 4-anisaldehyde and salicylaldehyde with acetoacetanilide in ethanol containing catalytic amount of piperidine furnished the corresponding α,β-unsaturated compounds 2a-c.
The reaction of α,β-unsaturated compound 2a with acetoacetanilide (1) proceeds in ethanol containing DROPs of conc HCl as a catalyst to afford the corresponding N-phenyl-2-pyridinone derivative 6.
The base-prompted reaction of the acidic methylene compound 7 with phenyl isothiocyanate in dry DMF at room temperature in basic medium led to the formation of the non-isolable intermediates 8 which underwent insitu heterocyclization reaction with chloroacetyl chloride to afford the corresponding bis-thiazolidin-5-one derivative 9
Insitu treatment of the non-isolable intermediates 8 with dilute HCl gave the corresponding bis-thiocarbamoyl derivatives 10a and 10b. Refluxing of 10 with chloroacetic acid afforded the corresponding bis-thiazolidin-4-one derivatives 11. Treatment of bis-thiocarbamoyl derivative 10a with diazotized sulphanilic acid affected the acetyl cleavage (Japp-Klingmann reaction type) with the formation of arylhydrazono-thiocarbamoyl derivative 12
Treatment of compound 17b with two moles of thiourea in ethanol and sodium ethoxide to give corresponding bis-1,3-thiazine derivative 25.