Synthesis and characterization of new phthalimides linked to schiff ’s Bases

Dissertant

Abd al-Razzaq, Marwah Shawqi

Thesis advisor

al-Azzawi, Ahlam Maruf

Comitee Members

Khalil, Muhammad Rifat Ahmad

University

University of Baghdad

Faculty

College of Science

Department

Chemistry Department

University Country

Iraq

Degree

Master

Degree Date

2012

English Abstract

The present work involved synthesis of new phthalimides linked to Schiffs̕ bases through different strategies.

The work was divided into four main parts: 1.

The first part involved synthesis of phthalimides linked to Schiff bases through phenyl sulfonamido group [5-18] Scheme(1).

Performing this part include the following steps: a.

Synthesis of N-phenyl phthalamic acid [1] via reaction of phthalic anhydride with aniline.

b.

Dehydration of the synthesized phthalamic acid by acetic anhydride and anhydrous sodium acetate as dehydrating agent producing Nphenyl phthalimide [2].

c.

The synthesized N-phenyl phthalimide was introduced in chlorosulfonation reaction producing phthalimidyl phenyl sulfonyl chloride [3].

d.

Phthalimidyl phenyl sulfonyl chloride was treated with hydrazine hydrate producing phthalimidyl phenyl sulfonyl hydrazine [4].

e.

Reaction of compound [4] with different aromatic aldehydes and ketones producing the target compounds [5-18].

2.

The second part involved synthesis of new phthalimides linked to Schiffs̕ bases through phenyl sulfonate moiety [20-26] Scheme(2).

Performing this part involved the following steps: a.

Synthesis of phthalimidyl phenyl sulfonate acetophenone [19] via reaction of the synthesized phthalimidyl phenyl sulfonyl chloride with 4-hydroxy acetophenone.

viii b.

Reaction of compound [19] with different primary aromatic amines producing the desired compounds [20-26].

3.

The third part involved synthesis of new phthalimides linked to Schiffs̕ bases through phenyl sulfonate moiety [28-33]Scheme(3).

This part involved the following steps: a.

Synthesis of phthalimidyl phenyl sulfonate benzaldehyde [27] via reaction of the synthesized phthalimidyl phenyl sulfonyl chloride with 4-hydroxy benzaldehyde.

b.

Reaction of compound [27] with different primary aromatic amines producing the desired compounds [28-33].

4.

The fourth part involved synthesis of new phthalimides linked to Schiffs̕ bases through methylene group [35-40].

Performing this part includes the following steps: a.

Synthesis of N-[4-phenyl phenacyl] phthalimide [34] via reaction of phthalimide potassium salt with 4-phenyl phenacyl bromide.

b.

Reaction of compound [34] with different primary aromatic amines producing the desired compounds [35-40] Scheme(4).

All the synthesized compounds were characterized by FT-IR spectroscopy and 1H-NMR , 13C-NMR spectra for some of them.

5.

Antibacterial activity for some of the synthesized imides were evaluated against two types of bacteria and the results showed that most of them have a good antibacterial activity

Main Subjects

Chemistry

No. of Pages

117

Table of Contents

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Language

English

Data Type

Arab Theses

Record ID

BIM-599660