الفهرس 
Chapter (1): IntroductionOnly 14 pages are availabe for public view
 |  | from | 208 |  |  |
| | | from | 208 | | |
Abstract
his thesis describes the studying synthesis of new phthalazine derivatives
through the reaction of nucleophiles a with the key intermediates with the
aim to evaluate their biological activities.
1. Preparation of the key intermediate phthalazinone derivative 3(a,b):
The reaction of phthalic anhydride 1 with benzene or chlorobenzene in the
presence of anhydrous AlCl3 were carried out under reflux condition at 80 °C
to produce aroyl benzoic acid derivatives 2(a,b). Further cyclisation with
hydrazine hydrate to give corresponding intermediate 3(a,b), the key
intermediate phthalazine derivatives 4(a,b) was synthesized by chlorination of
3(a,b) through dehydroxychlorinated by POCl3 in a heating mixture of DMF
and acetonitrile Scheme 1
2. Synthesis of amino phthalazine derivatives 5,6(a-c).
Reactions of phthalazine derivatives 4(a,b) with nitrogen containing
nucleophiles such as aniline, m-methyl aniline and p-chloro aniline in dry
chloroform affording 5,6(a-c).
3. Synthesis of 1-oxo-Arylphthalazine sulphonylchloride 7(a,b), and
sulphonylhydrazide 8(a,b).
Arylphthalazine derivatives 3(a,b) were added portion wise to
chlorosulphonic acid in the presence of excess amount of thionylchloride at 0 oC
with stirring , the temperature was elevated to 90 oC for 72 hours , the reaction
mixture was poured into crushed ice , the products were filtered off to give
7(a,b), an treatment with hydrazine hydrate in THF at room temperature
affording 8(a,b) in good yields.
4. Synthesis of 1-oxophthalazine sulphonylhydrazone derivatives 9, 10(a-d)
and 11, 12(a-c).
A mixture of phthalazine sulfonylhydrazide 8(a,b) and aldehyde
derivatives such as benzaldehyde, p-chlorobenzaldehyde, anisaldehyde, and mbromobenzaldehyde
or sugar derivatives such as D-glucose, D-arabinose and Dxylose
in ethanol with catalytic amount of glacial acetic acid were reflux for 2
hours followed reaction affording 9,10(a-d) and 11,12(a-c) in good yields.
5. Synthesis of 1-oxophthalazine carboxamide and carbothioamide
derivatives 13, 14(a,b).
A mixture of compound 3(a,b) and phenylisocyanate or phenylisothiocyanate
in benzene was refluxed for 8 hours , follow reaction to give 13,14(a,b).
6. Reaction with pipredine under Mannich condition 15(a,b).
A mixture of compound 3(a,b) and pipredine and formaldehyde solution and
DROP of HCl in ethanol was refluxed for 4 hours , followed reaction affording
15(a,b).
The structures of all synthesized compounds were characterized by various
spectral techniques. (C.f. EX. part)
Biological activity
All synthesized compounds witch tested against C. Pipiens larval proved to a
promising controlling against C. Pipiens larval.