الفهرس 
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Abstract
This thesis includes four chapters. The first chapter is an introduction which comprises a
review of the chemistry ofthe isatins (lH-indole-2,3-diones). The most important methods
I’ of synthesis of these compounds, as well as their reactions and their biological activities
are considered.
The second chapter is devoted to a discussion of the original work of the candidate
regarding the synthesis of the new hydrazones family, pyrazolopyrimidino-
indolinonehydrazones and the novel tetra heterocyclic family, indolo[2,3-e]-
pyrazolo[l’,5’:3,4]pyrimido[2,1-c][1,2,4]triazines, as well as study of their reactions. Thus,
a series of (E)-3-{2-(2,5-diphenylpyrazolo[1,5-c]pyrimidin-7-yl)hydrazono }indolin-2-ones
(113a-c) were prepared by the reaction of the 2,5-diphenyl-7-hydrazinopyrazolo[1,5-c]-
pyrimidine (111) with the respective IH-indole-2,3-diones (112a-c) in dioxan at room
temperature, which upon boiling in dioxan yielded the corresponding (Z)-pyrazolo-
pyrimidinoindolinonehydrazones 114a-c in excellent yields.
The structure of both (E and Z) pyrazolopyrimidinoindolinonehydrazones was fully
established, besides elemental analysis, by study of their spectral characteristic including
infrared, IH NMR and mass spectra. The infrared of 113a-c showed that, in the solid state
they exist predominantly in the ketone forms (l13A and 113B). The infrared spectra could
not differentiate between (E)- and (Z)-pyrazolopyrimidinoindolinonehydrazones 113 and
114 however, the IH NMR spectra in DMSO-d6 indicated that, 113 exist in the (E)
conformer either in the ketone or enol forms (l13A, 113B or 113C), while 114 exist in the
(Z) conformer due to the presence of hydrogen bond.
Some electrophilic substitution reactions of (E)-pyrazolopyrimidinoindolinone-
hydrazones 113a-c were studied. The reactions included halogenation, nitration in acetic
acid at room temperature and reaction with benzenediazonium chloride led to the
introduction of electrophiles at position 3 with the formation of (Z) conformer. Since (E)-
pyrazolopyrimidinoindolinonehydrazones 113 in acidic media were isomerized into the (2)
conformers. Thus, brornination of (E)-pyrazolopyrimidinoindolinonehydrazones in acetic
acid afforded (Z)-3-bromo-derivatives due to isomerization of (E) conformer into (Z)
conformer at first followed by brornination giving the products, this was confirmed by
synthesis of the isomeric (E)-3-bromopyrazolopyrirnidinoindolinonehYdrazones 119a-c by
the bromination of 2,5-diphenylpyrazolo[ 1 ,5-c ]pyrirnidine-7( 6H)-thione (110) giving
3-bromo-2,5-diphenylpyrazolo[ 1 ,5-c ]pyrimidine-7 (6H)-thione (117), which reacted with
hydrazine hydrate in refluxing ethanol to produce 3-bromo-7-hydrazino-2,5-diphenyl-
pyrazolo[1,5-c]pyrimidine (118). Stirring of 118 with the respective IH-indole-2,3-diones
(112a-c) in dioxan at room temperature afforded the corresponding (E)-3-bromopyrazolo-
pyrimidinoindolinonehydrazones 119a-c, which are different in TLC and IH NMR than
116a-c. Boiling of 119a-c in dioxan giving the respective (Z)-3-bromopyrazolo-
pyrimidinoindolinonehydrazones 116a-c.