Isatin reacts with N-(2-aminoethyl)-1,3-propanediamine in a 1:1 molar ratio in ethyl alcohol to give new Schiff base, 4-[2-(2-oxoindolin-3-ylideneamino)ethylamino.-3,4-dihydro-2H-pyrido[3,2-b]indole. When the reaction is carried out by fusion, two new Schiff bases, 3-(vinylimino)indolin-2-one and 3-(allylimino)indolin-2-one, are obtained with the liberation of ammonia gas. The synthesis, characterization, and the reactivity of the Schiff bases with mercury(II) acetate and palladium(II) chloride are studied. Elucidation of the structures are based on elemental analyses and infrared (IR), ultraviolet (UV), 1H-nuclear magnetic resonance (NMR), and mass spectroscopic (MS) spectra.

Novel Organometallic Compounds Via Metallation of Some New Schiff Bases

Metallation of new imines 2-(4-(Dimethylamino)benzylidene- amino)benzenethiol (1) and 2-(4-nitrobenzylideneamino)-benz- enethiol(5) with Hg(II), Ni(II) acetate, and palladium chloride afforded metallated products (2), (3), and (4) in the form of monomercurated, dinickel nickel bis-, monopalladated products and monometallated products of Hg++ and Ni++ (6) and (7), and monopalladated cyclized product (8), respectively. Compounds (1) and (5) were prepared from the reaction of o-aminothiophenol with N,N-dimethylaminobenzaldehyde and p-nitrobenzaldehyde in ethyl alcohol. Elemental analyses, IR, 1HNMR, and mass spectral elucidated the structures. All the newly synthesized compounds have been evaluated for their antimicrobial activity against gram positive and gram negative bacteria and fungi. Compounds (4) and (8) exhibited in vitro anticancer activity toward breast cancer.

Metallation of Some New Imines and Evaluation of Their Antimicrobial and Anticancer Activity

Schiff bases are prepared via the reaction of 1,3-propanediamine with isatin in alcohol. The reaction depends on the mode of addition. The addition of isatin in alcohol to the diamine in alcohol afforded two products - a major product and a minor one. The obtained data confirmed that the two products are isomers. When the addition was reversed, another product was obtained. As the reaction mixture was left overnight, a product was obtained, which was found to be an isomer. The reaction was repeated in solid state by fusion or in microwave to give the same product. The synthesis, characterization and the reactivity of the Schiff bases with mercury(II) acetate and palladium(ΙΙ) chloride were studied. The structures of the products are confirmed by elemental analyses, IR, UV/Vis, 1 H NMR and mass spectra.

W. A. Mokbel

Papers

Synthesis of organopalladium and organomercury compounds via metallation of some new Schiff bases