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العنوان
Some New Approaches For Synthesis Of Pyridines And Their Condensed Derivatives /
المؤلف
Abd-Elazez,Ghada W.
هيئة الاعداد
باحث / غادة وجيه عبد العزيز
مشرف / محمد إبراهيم
مشرف / احمد الغندور
مشرف / حسني علي
الموضوع
Pyridine.
تاريخ النشر
1996.
عدد الصفحات
75 P. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
Organic Chemistry
تاريخ الإجازة
26/12/1996
مكان الإجازة
اتحاد مكتبات الجامعات المصرية - الكيمياء
الفهرس
Only 14 pages are availabe for public view

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from 164

Abstract

Part (I) synthesis of novel derivatives of 4-methylthio-n-aryl-2-pyridones and deazapurine analogues : reaction of ketene jxthioacetals with substituted acetaniijpes : it has been found that both [bis(methylthio)methyiene]malononitrile 2a and ethyl 2-cyano-3,3-bis(methylthio)acrylate 2b reacted with substituted acetanilides 3a-c in sodium ethoxide or potassium hydroxide in dioxan to give the corresponding 4-methylthio-n-aryl-2-pyridones 5. The structures of 5 were established and confirmed for the reaction products on the basis of their elemental analysis and spectral data (ms, 1h nmr and ir). The formation of 5 from the reaction of 2 with 3 is assumed to proceed through intermediating of 4, which were cyclized to yield the final 4-methylthio-2-pyridones 5. Compounds 5 bearing methylthio group and other latent functional substituents were found useful for the synthesis of fused derivatives. Thus, it has been found that compounds 5 reacted with aromatic amines in fusion to afford the corresponding 4-anilino derivatives 6. The structures of compounds 6 were established on the basis of their elemental analysis and spectral data (ms, 1h nmr and ir). When compounds 5 were subjected to the reaction with hydrazine, the hydrazino derivatives could not be isolated but cyclized to the pyrazolo[4,3-c] pyridine derivatives 7. The structures of compounds 7 were established on the basis of their elemental analysis and spectral data (ms, 1h nmr and ir).
Part(II) synthesis of novel n-glycqsylated 2-pyridinethiones : pyridine-2(1h)-thione derivative 3 reacted with 2,3,4,6-tetra-o-acetyl-a-d-gluco- and galactopyranosyi bromides in the presence of aqueous potassium |hydroxide to give the corresponding n-glucosyl 6a and n-galactosyl pyridine-r1h)-thione derivative 7a. Although the coupling of 3 with glucosyl bromide could also give the corresponding thioglycosides, the formation of the n-jjglycoside derivatives 6a and 7a were proved chemicaly and confrimed by their elemental analysis and spectral data (ms, ir, uv, 1h nmr and ,3c nmr). Reaction of 3 with hexamethyldisilazane (hmds) in the presence of ammonium sulfate gave the corresponding 2-trimethylsiliylthiopyridines 5, which were subsequently treated with peracetylated sugars in the presence of tedistilled sncu to afford the corresponding n-glycosylpyridine-2(1h)-thione derivatives. Compounds 6a and 7a were deblocked through treatment with methanolic ammonia to give the free glycosides 6b and 7b respectively. The structures of the reaction products 6b and 7b were established and confrimed by their elemental analysis and spectral data (ms, ir, uv, 1h nmr and 13c nmr).