الفهرس 
Synthesis of isatin and isatin derivativesOnly 14 pages are availabe for public view
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Abstract
Utility of carbonyl compounds in heterocyclic synthesis
This thesis describes the utility of isatin as a key starting
material for the preparation of a novel series of isatins
derivatives and studies the antimicrobial and fluorescent
activities of these compounds.
Synthesis of spiro[indoline-3,4’-pyridine]-3’,5’-dicarbonitrile II
derivatives
Spiro-indoline pyridine II was synthesized to be used as a
starting material for synthesizing some new heterocyclic
compounds containing isatin moiety. It was found that the
reaction of isatylidene malononitrile I with malononitrile and
ethyl thiol in presence of ammonium acetate gave compound II
when the reaction was continued for 10 min at 55oC (Scheme
A).
Scheme A
Study on 2’-amino-6’-(ethylthio)-2-oxo-1’H-spiro[indoline-3,4’-
pyridine]-3’,5’-dicarbonitrile II
The compound II reacted with carbon disulfide in
refluxing pyridine afforded carbamodithioic acid derivative III.
Also, the reaction of compound II with triethyl orthoformate,
dimethylformamide dimethyl acetal, and maleic anhydride
yielded the compounds IV, V, and VI respectively (Scheme B).
Summary
2
Scheme B
Also, the alkylation of compound II with α-halo acetic acid
derivatives (chloroacetonitrile and ethyl bromoacetate) was
achieved in dry acetone containing anhydrous potassium
carbonate and afforded the compounds VII and VIII
respectively, while the reaction of II with hydrazine hydrate
afforded pyrrole derivative IX (Scheme C).
Scheme C
Moreover, active methylene compounds such as
malononitrile, ethyl acetoacetate, diethylmalononate, and
malononitrile with acetaldehyde afforded the compounds X,
XII, XIII, and XI respectively (Scheme D).
Summary
3
Scheme D
Oxazine and pyrimidine derivatives synthesized by the
reaction of compound II with acetic anhydride, formic acid, and
phenyl isothiocyanate afforded the compounds XIV, XV, and
XVI (Scheme E).
Scheme E
Summary
4
Synthesis of 2-(2-Oxoindolin-3-ylidene)hydrazine-1-carbox-
imidamide Ia derivatives
The reaction of isatin with aminoguanidine in aqueous
ethanol in presence of a catalytic amount of hydrochloric acid
yielded 2-(2-oxoindolin-3-ylidene)hydrazine-1-carboximid-
amide Ia, while in presence of a catalytic amount of
concentrated sulfuric acid yielded N-2-bis(2-oxoindolin-3-
ylidene)hydrazine-1-carboximidamide IIa (Scheme F).
Scheme F
Study on 2-(2-Oxoindolin-3-ylidene)hydrazine-1-carboximid-
amide Ia
Cyclization of 2-(2-oxoindolin-3-ylidene)hydrazine-1-
carboximidamide Ia in presence of catalytic piperidine in
aqueous ethanol produced IIIa. while the reaction of Ia with
hydrazine hydrate afforded N’-(2-oxoindolin-3-ylidene)
hydrazinecarboximidhydrazide IVa (Scheme G).