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العنوان
Studies on utilization of isothiocyanates and enamines in heterocyclic synthesis /
المؤلف
Mohamed, Islam Ragab Abd El-ghany.
هيئة الاعداد
باحث / اسلام رجب عبد الغنى محمد
مشرف / ا.د / محمد جمعه محمد عاصى
مشرف / د / عنايات كامل محمد
مشرف / د / أميره عاطف غنيم
الموضوع
Heterocyclische verbindingen.
تاريخ النشر
2013.
عدد الصفحات
202 P. :
اللغة
الإنجليزية
الدرجة
الدكتوراه
التخصص
الكيمياء
تاريخ الإجازة
1/1/2013
مكان الإجازة
جامعة الزقازيق - كلية العلوم - الكيمياء
الفهرس
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Abstract

The reaction of aniline with acylisothiocyante 1 gave 1,3-thiourea derivative 2 which underwent intramolecular cycloaddition by treatment with sodium ethoxide and stirring gave at room temperature thiazineone derivative 3 while upon reflux gave pyrimidine derivative 4. Also treatment of compound 1 with phenylenediamine led to formation of benzimidazolo pyrimidine derivative 6. Compound 1 was allowed to react with aminoesrer producing thiophene derivative 7 which upon refluxing in sodium ethoxide gave thiouracil 8. The reaction of compound 1 with enaminones 9 and 11 led to form acetyl pyrimidine 10 and acetyl pyridine derivatives 14 respectively. Acylisothiocyanate 1 was allowed to react with benzylidene malononitrile producing oxazine derivative 15. Also compound 1 was reacted with sodium azide followed refluxing with sodium ethoxide affording thiazinotetrazole derivative 18. The reaction of acetylacetone with compound 1 gave pyridine derivative 20 by intramolecular cycloaddition while it was reacted with N-methyl aniline affording thiazine derivative 22. Also it was reacted with cyanoacetamide producing mercaptopyrimidine derivative 24. Compound 1 was refluxed with phenylhydrazine, urea, guanidinum carbonate and anthranilic acid in the presence of dry acetone affording triazole derivative 28, N-substituted pyrimidine 32, compound 33 and thiopyrimidine derivative 34 respectively. Pyrimidinthione 36 and pyridinthione derivative 37 are obtained from the reaction of enamine 11 with benzoyl isothiocyanate. Condensation of compound 36 with ethyl acetate afforded quinoxaline derivative 39. pyridinothiothiazole 42 was prepared by the reaction of compound 37 with sodium hypochloride. Alkylation of compound 37 with chloro acetic acid yielded thienopyridine 44. Condensation of 37 with diethyl oxalate afforded pyridopyridine derivative 46. Addition of benzylidene malononitrile to enamine 11 yielded pyridine 49. Heterocyclocondensation of benzylidene cyanoacetamide derivative and enamine 11 yielded hydroxypyridene 50. Compound 11 was reacted with potassium isothiocyanate affording oxathiazol 51 and with ethyl cyanoacetate afforded pyridinone derivative 52.