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العنوان
STUDIES ON SOME NITROGEN
CONTAINING HETEROCYCLIC COMPOUNDS\
المؤلف
EL-SAYED,ABEER MOHAMED
هيئة الاعداد
مشرف / محمد على حسن
مشرف / محمد محمود محمد
مشرف / سيد احمد شيبة
مناقش / امتثال احمد الصاوى
تاريخ النشر
1998.
عدد الصفحات
194p.;
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
Organic Chemistry
تاريخ الإجازة
1/1/1998
مكان الإجازة
جامعة عين شمس - كلية العلوم - قسم الكيمياء الحيوية
الفهرس
Only 14 pages are availabe for public view

from 194

from 194

Abstract

The work reported in this thesis is aiming to study the reactivity of 2-oxo(thioxo)pyridine
derivatives towards some organic reagents.
3-cyano-4,6-dimethyl-2(1H)-pyridone (1) and pyridin­ thione (2) have been synthesized. Pyridone (1)
reacted with phosphorus oxychloride to give 2-chloropyridine (3), which is reacted with sodium
ethoxide, p-anisidine or sodium azide to give the corresponding 2-ethoxy, 2-p-methoxyphenyl­ amino
derivatives (4 and 5), or tetrazolopyridine’ (6), respectively. The 2-oxo(thioxo)pyridines (1,2)
underwent base catalyzed condensation with aromatic aldehydes to give 4-styrylpyridene
derivative (7) and/or bis-pyridin-4-yl­ propane derivative (8).
Also, 3-cyano-2-oxo(thioxo )pyridines (1,2) were reacted with Grignard reagents to give the
corresponding 3-acyl derivatives (9). The 3-acetylpyridone (9a) reacted with phenylhydrazine,
hydrazine hydrate, aromatic aldehydes or POCh to give the phenylhydrazone (10), the azine (11),
the propenones (12) or 2-chloro-3-acetylpyridine (13), respectively.
One the other hand, alkylation of2-oxopyridine (1)
by some organic halogen compounds under phase transfer
catalysis conditions, afforded predominantly N-alkylation
products (14), in addition to 0-alkylation product (15) only in case of methylation, while
2-thioxopyridine (2) yielded, exclusively, the S-alkylated pyridones (17) and thiopheno­ pyridine
(18). However, PIC-alkylation of(1), in presence of CS2, yielded the thin-derivative (16).
2-0xopyridine (1) and its N-methyl derivative (14a)
were subjected to react with some reactive dienophiles under thermal Diels-Alder condition to give
the corresponding bicycloadducts (20 and 21).
Ou the other hand, the 3-cinnamoylpyridone (12b) acting as an a,j3-unsaturated ketone, which is
reacted with some active methylene compounds in presence of different catalytic bases at different
reaction conditions via a Michael route addition or cycloaddition reaction to give the adducts
(22-31). Also, the propenone (12b) is condensed with hydrazines and hydroxylamine to give the
corresponding pyridylpyrazolines (32) and isooxazolopyridine (33), respectively.
Elemental analysis, IR, 1H-NMR, 13C-NMR and mass
spectra were used to establish the structures of the products.