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العنوان
/Studies on cyclic imides
المؤلف
Khalil, ahmed.
هيئة الاعداد
باحث / ahmed khalil
مشرف / mohamed younes
مناقش / abd elfatah shaaban
مناقش / mohamed younes
الموضوع
chemistry.
تاريخ النشر
1984 .
عدد الصفحات
111p. :
اللغة
الإنجليزية
الدرجة
ماجستير
التخصص
الكيمياء
تاريخ الإجازة
1/1/1984
مكان الإجازة
جامعة بنها - كلية العلوم - كمياء
الفهرس
Only 14 pages are availabe for public view

from 152

from 152

Abstract

In the present investigation, N-(phthalimido]-acetoxy, o-jrn-, and p-benzoyloxy
phthalimides (III a-d) were obtained from the reaction of phthaloxime
(I) with phthalimidoacetyl chloride, o-vm-, and p-phthalimidobenzoyl chlorides
(II a-d).
N-[phthalimido]-acetoxy phthalimide (III a) undergoes hydrolysis with
(70 %) H2SOlf to give a mixture of phthalic acid (IV) and glycine (V).
N-[phthalimido]-acetoxy phthalimide (III a) undergoes base-catalyzed
ring opening with aromatic amines and aminobenzoic acids to give the corresponding
N-aryl-phthalimides (VI a-g) and anilides (VII a-g).
Similarly (III a), reacts with hydrazine hydrate in fluxing benzene to
give mixture of phthalhydrazide (VIII), and N-phthalimidoacetic acid hydrazide
(IX); and with phenyl hydrazine to give a mixture of N-anilino-phthalirnide
(X) and phthalimidoacetyl phenylhydrazine (XI).
N-(phthalimido]-acetoxy phthalimide (III a) undergo acid catalyzed
ring opening with anhydrous aluminium chloride (2 moles) in the presence
of reactive aromatic substrates to give the corresponding mixtures of If-aryl-
2,3,I-benzoxazone (XII a-c) and the corresponding aryl-phthalimidomethyl
ketone (XIII a-c) •.
Also (III a) react with (6 moles) anhydrous aluminium chloride in the
presence of reactive aromatic substrates to give the corresponding mixtures
of o-aryl-anilides (XIV a-c) and aryl-phthalimidomethyl ketones (XIII a-c).
-ii-
And Also, in the present invistigation, benzoyloxy phthalimide was
introduced of phthalimido moiety in o-,m-, and p-position to see their effects
on the mode of the reactions and also to see the bulky effects of o-,m-
, and p-substitution on the mode of reaction.
Also; N-[phthalimido]-benzoyloxy phthalimides (III b-d) undergo hydrolysis
with (70 %) H2S04 to give a mixture of phthalic acid (IV) and the corresponding
aminobenzoic acid (XV a-c).
N-[Phthalimido]-benzoyloxy phthalimides (III b-d) undergo base-catalyzed
ring opening with aromatic amines and aminobenzoic acids to give the corresponding
N-aryl-phthalimides (VI a-u) and anilides (XVI a-u),
Similarly (III b-d) react with hydrazine hydrate to give the corresponding
mixture of phthalhydrazide (VIII) and N-[phthalimido]-o-,m-, and p-benzoic
acid hydrazide (XVII a-c); and with phenyl hydrazine to give a mixture
of N-anilinophthalimide (X) and the corresponding phthalimidobenzoyl phenylhydrazines
(XIX a-c).
N-[phthalimido]-benzoyloxy phthalimides (III b-d) undergo acid-catalyzed
ring opening with anhydrous aluminium chloride (2 moles) in the presence
of reactive aromatic substrates to give a mixture of 4-phenyl-2,3,I-benzoxazones
(XII a-c) and N-[aroylphenyJ]-phthalimides (XX a-c),(XXI a-c),(XXII a-c).
Also, (III b-d) react with (6 moles) anhydrous aluminium chloride in
the presence of reactive aromatic substrates to give the corresponding
mixtures of o-uroylanilides (XIV a-c) and N-[aroylphenyJ]-phthalimides