Synthesis and Characterization of Some New Symmetrical Bis-Isatins Derived From p-Substituted Aromatic Amines

Authors: Faiq H. S.Hussain & Hussein K A. Khudhur

Abstract:  A series of p-substituted isonitrosoacetanilide 2(a-g) were prepared via the condensation of p-substitutedaromatic amines (benzene-1,4-diamine,o-tolidine,4,4’-diaminodiphenylmethane, p bromoaniline p-nitroaniline, p-aminobenzoic acid and p-toluidine) with chloral hydrate and hydroxylamine hydrochloride in aqueous solution of sodium sulfate and absolute ethanol as a co-solvent under reflux conditions. The compounds 2(a-g) were cyclized in the presence of a strong acid to obtain 5-sudstituted isatin 3(a-f), which were condensed with aromatic diamines to some new bis-azomethine of isatin 4(a-h) in the presences of catalytic amounts of glacial acetic acid in EtOH. On the other hand some new bis Azomethine of isatin 5(a-d) were synthesized, from the reaction of di-isatins with aromatic monoamines (pyridin-2-amine and 5-chloropyridin-2-amine) in the presences of catalytic amounts of glacial acetic acid in DMSO. The new synthesized compounds were identified using spectroscopic techniques (IR, 1H-NMR, 13C-NMR, DEPT-135, Elemental analysis and Mass Spectroscopy). Finally the prepared compounds have been screened for antimicrobial activity in vitro against two types of bacteria Staphylococcus-aureus (Gr+ve) and Escherichia-coli (Gr-ve) the results showed that most of the prepared compounds are sensitive against both types of tested bacteria.

Keywords: Bis-Isonitrosoacetanilide , 5-Substituted Isatin , Bis-Isatins, Bis-Azomethine

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doi: 10.23918/eajse.v4i1sip56

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