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Some reactions of 8-aminoquinoline
Author
Thong, Kar Fong
Supervisor
Khoo, Lian Ee
Abstract
The reactions between 8-aminoquinoline and R2SnC12 (R - Ph, Me, n-Bu) have been carried out. 8-Aminoquinoline was found to form a stable 1:1 adduct, dichlorodiphenyl(8-aminoquinoline)tin(IV) (11a), with Ph2SnC12, as reported. With Me2SnC12:, it reacted to yield dichlorodimethyl(8-aminoquinoline)tin(lV) (11b), which was more stable in anhydrous benzene than in 'reagent-grade' CHC13. However, with n-Bu2SnC12, irrespective of the solvent used, 8-aminoquinoline was protonated at the p!ridyl nitrogen atom, leading to the formation of 8-aminoquirlolinium chioride (12).
(l11a) and (12) were prepared and characterized. They were required as the essential materials for studying the feasibility of the hydrolyzing reaction. UV spectroscopy was especially adopted to characterize the starting materials [ (11a) and (11b) ] and the decomposed products (12). The evidences gathered from a series of UV spectra indicated that these complexes, (11a) and (11b), would hydrolyze in the presence of water. This experimental result has an important implication in the mode of action for antitumour activity of diorganotin complexes.
In addition, (11b) which is s potential antitumour agent was successfully isolated. IR and NMR studies indicated the possession of a pair of cis chlorides and this was further confirmed by preliminary X-ray determination of the structure. This property is an important requirement for complexes to exhibit antitumour activity. The synthesis was further extended to the isolation of 8-amonioquinolinium dichloride (22) and 8-ammonioquinolinium diphenyltetrachlorostannate (23). These two new compounds were characterized spectroscopically. Hopefully, X-ray crystallography analysis can be carried out with the intention of determining the structural parameters important for antitumour activity.
(l11a) and (12) were prepared and characterized. They were required as the essential materials for studying the feasibility of the hydrolyzing reaction. UV spectroscopy was especially adopted to characterize the starting materials [ (11a) and (11b) ] and the decomposed products (12). The evidences gathered from a series of UV spectra indicated that these complexes, (11a) and (11b), would hydrolyze in the presence of water. This experimental result has an important implication in the mode of action for antitumour activity of diorganotin complexes.
In addition, (11b) which is s potential antitumour agent was successfully isolated. IR and NMR studies indicated the possession of a pair of cis chlorides and this was further confirmed by preliminary X-ray determination of the structure. This property is an important requirement for complexes to exhibit antitumour activity. The synthesis was further extended to the isolation of 8-amonioquinolinium dichloride (22) and 8-ammonioquinolinium diphenyltetrachlorostannate (23). These two new compounds were characterized spectroscopically. Hopefully, X-ray crystallography analysis can be carried out with the intention of determining the structural parameters important for antitumour activity.
Date Issued
1997
Call Number
RC271.C5 Tho
Date Submitted
1997